Cleavable Biotin Probes for Labeling of Biomolecules via Azide−Alkyne Cycloaddition
The azide−alkyne cycloaddition provides a powerful tool for bio-orthogonal labeling of proteins, nucleic acids, glycans, and lipids. In some labeling experiments, e.g., in proteomic studies involving affinity purification and mass spectrometry, it is convenient to use cleavable probes that allow rel...
Saved in:
| Published in | Journal of the American Chemical Society Vol. 132; no. 51; pp. 18351 - 18360 |
|---|---|
| Main Authors | , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
29.12.2010
Amer Chemical Soc |
| Subjects | |
| Online Access | Get full text |
Cover
Loading…
| Abstract | The azide−alkyne cycloaddition provides a powerful tool for bio-orthogonal labeling of proteins, nucleic acids, glycans, and lipids. In some labeling experiments, e.g., in proteomic studies involving affinity purification and mass spectrometry, it is convenient to use cleavable probes that allow release of labeled biomolecules under mild conditions. Five cleavable biotin probes are described for use in labeling of proteins and other biomolecules via azide−alkyne cycloaddition. Subsequent to conjugation with metabolically labeled protein, these probes are subject to cleavage with either 50 mM Na2S2O4, 2% HOCH2CH2SH, 10% HCO2H, 95% CF3CO2H, or irradiation at 365 nm. Most strikingly, a probe constructed around a dialkoxydiphenylsilane (DADPS) linker was found to be cleaved efficiently when treated with 10% HCO2H for 0.5 h. A model green fluorescent protein was used to demonstrate that the DADPS probe undergoes highly selective conjugation and leaves a small (143 Da) mass tag on the labeled protein after cleavage. These features make the DADPS probe especially attractive for use in biomolecular labeling and proteomic studies. |
|---|---|
| AbstractList | The azide−alkyne cycloaddition provides a powerful tool for bio-orthogonal labeling of proteins, nucleic acids, glycans, and lipids. In some labeling experiments, e.g., in proteomic studies involving affinity purification and mass spectrometry, it is convenient to use cleavable probes that allow release of labeled biomolecules under mild conditions. Five cleavable biotin probes are described for use in labeling of proteins and other biomolecules via azide−alkyne cycloaddition. Subsequent to conjugation with metabolically labeled protein, these probes are subject to cleavage with either 50 mM Na2S2O4, 2% HOCH2CH2SH, 10% HCO2H, 95% CF3CO2H, or irradiation at 365 nm. Most strikingly, a probe constructed around a dialkoxydiphenylsilane (DADPS) linker was found to be cleaved efficiently when treated with 10% HCO2H for 0.5 h. A model green fluorescent protein was used to demonstrate that the DADPS probe undergoes highly selective conjugation and leaves a small (143 Da) mass tag on the labeled protein after cleavage. These features make the DADPS probe especially attractive for use in biomolecular labeling and proteomic studies. The azide-alkyne cycloaddition provides a powerful tool for bio-orthogonal labeling of proteins, nucleic acids, glycans, and lipids. In some labeling experiments, e.g., in proteomic studies involving affinity purification and mass spectrometry, it is convenient to use cleavable probes that allow release of labeled biomolecules under mild conditions. Five cleavable biotin probes are described for use in labeling of proteins and other biomolecules via azide-alkyne cycloaddition. Subsequent to conjugation with metabolically labeled protein, these probes are subject to cleavage with either 50 mM Na(2)S(2)O(4), 2% HOCH(2)CH(2)SH, 10% HCO(2)H, 95% CF(3)CO(2)H, or irradiation at 365 nm. Most strikingly, a probe constructed around a dialkoxydiphenylsilane (DADPS) linker was found to be cleaved efficiently when treated with 10% HCO(2)H for 0.5 h. A model green fluorescent protein was used to demonstrate that the DADPS probe undergoes highly selective conjugation and leaves a small (143 Da) mass tag on the labeled protein after cleavage. These features make the DADPS probe especially attractive for use in biomolecular labeling and proteomic studies.The azide-alkyne cycloaddition provides a powerful tool for bio-orthogonal labeling of proteins, nucleic acids, glycans, and lipids. In some labeling experiments, e.g., in proteomic studies involving affinity purification and mass spectrometry, it is convenient to use cleavable probes that allow release of labeled biomolecules under mild conditions. Five cleavable biotin probes are described for use in labeling of proteins and other biomolecules via azide-alkyne cycloaddition. Subsequent to conjugation with metabolically labeled protein, these probes are subject to cleavage with either 50 mM Na(2)S(2)O(4), 2% HOCH(2)CH(2)SH, 10% HCO(2)H, 95% CF(3)CO(2)H, or irradiation at 365 nm. Most strikingly, a probe constructed around a dialkoxydiphenylsilane (DADPS) linker was found to be cleaved efficiently when treated with 10% HCO(2)H for 0.5 h. A model green fluorescent protein was used to demonstrate that the DADPS probe undergoes highly selective conjugation and leaves a small (143 Da) mass tag on the labeled protein after cleavage. These features make the DADPS probe especially attractive for use in biomolecular labeling and proteomic studies. The azide-alkyne cycloaddition provides a powerful tool for bio-orthogonal labeling of proteins, nucleic acids, glycans, and lipids. In some labeling experiments, e.g., in proteomic studies involving affinity purification and mass spectrometry, it is convenient to use cleavable probes that allow release of labeled biomolecules under mild conditions. Five cleavable biotin probes are described for use in labeling of proteins and other biomolecules via azide-alkyne cycloaddition. Subsequent to conjugation with metabolically labeled protein, these probes are subject to cleavage with either 50 mM Na2S2O4, 2% HOCH2CH2SH, 10% HCO2H, 95% CF3CO2H, or irradiation at 365 nm. Most strikingly, a probe constructed around a dialkoxydiphenylsilane (DADPS) linker was found to be cleaved efficiently when treated with 10% HCO2H for 0.5 h. A model green fluorescent protein was used to demonstrate that the DADPS probe undergoes highly selective conjugation and leaves a small (143 Da) mass tag on the labeled protein after cleavage. These features make the DADPS probe especially attractive for use in biomolecular labeling and proteomic studies. The azide-alkyne cycloaddition provides a powerful tool for bio-orthogonal labeling of proteins, nucleic acids, glycans, and lipids. In some labeling experiments, e.g., in proteomic studies involving affinity purification and mass spectrometry, it is convenient to use cleavable probes that allow release of labeled biomolecules under mild conditions. Five cleavable biotin probes are described for use in labeling of proteins and other biomolecules via the azide – alkyne cycloaddition. Subsequent to conjugation with metabolically labeled protein, these probes are subject to cleavage with either 50 mM Na 2 S 2 O 4 , 2% HOCH 2 CH 2 SH, 10% HCO 2 H, 95% CF 3 CO 2 H, or irradiation at 365 nm. Most strikingly, a probe constructed around a dialkoxydiphenylsilane (DADPS) linker was found to be cleaved efficiently when treated with 10% HCO 2 H for 0.5 h. A model GFP protein was used to demonstrate that the DADPS probe undergoes highly selective conjugation and leaves a small (143 Da) mass tag on the labeled protein after cleavage. These features make the DADPS probe especially attractive for use in biomolecular labeling and proteomic studies. The azide-alkyne cycloaddition provides a powerful tool for bio-orthogonal labeling of proteins, nucleic acids, glycans, and lipids. In some labeling experiments, e.g., in proteomic studies involving affinity purification and mass spectrometry, it is convenient to use cleavable probes that allow release of labeled biomolecules under mild conditions. Five cleavable biotin probes are described for use in labeling of proteins and other biomolecules via azide-alkyne cycloaddition. Subsequent to conjugation with metabolically labeled protein, these probes are subject to cleavage with either 50 mM Na(2)S(2)O(4), 2% HOCH(2)CH(2)SH, 10% HCO(2)H, 95% CF(3)CO(2)H, or irradiation at 365 nm. Most strikingly, a probe constructed around a dialkoxydiphenylsilane (DADPS) linker was found to be cleaved efficiently when treated with 10% HCO(2)H for 0.5 h. A model green fluorescent protein was used to demonstrate that the DADPS probe undergoes highly selective conjugation and leaves a small (143 Da) mass tag on the labeled protein after cleavage. These features make the DADPS probe especially attractive for use in biomolecular labeling and proteomic studies. |
| Author | Schuman, Erin M Hodas, Jennifer J. L Szychowski, Janek Mahdavi, Alborz Dieterich, Daniela C Tirrell, David A Ngo, John T Landgraf, Peter Bagert, John D |
| AuthorAffiliation | 2 Division of Biology, California Institute of Technology, 1200 E. California Blvd., MC 114-96, Pasadena, CA, 91125, USA 4 Max Planck Institute for Brain Research, Deutschordenstraße 46, 60528 Frankfurt, Germany 1 Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Blvd., MC 210-41, Pasadena, CA, 91125, USA 3 Leibniz-Institute for Neurobiology, Research Group Neuralomics, Brenneckestraße 6, 39118 Magdeburg, Germany |
| AuthorAffiliation_xml | – name: 1 Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Blvd., MC 210-41, Pasadena, CA, 91125, USA – name: 3 Leibniz-Institute for Neurobiology, Research Group Neuralomics, Brenneckestraße 6, 39118 Magdeburg, Germany – name: 4 Max Planck Institute for Brain Research, Deutschordenstraße 46, 60528 Frankfurt, Germany – name: 2 Division of Biology, California Institute of Technology, 1200 E. California Blvd., MC 114-96, Pasadena, CA, 91125, USA |
| Author_xml | – sequence: 1 givenname: Janek surname: Szychowski fullname: Szychowski, Janek – sequence: 2 givenname: Alborz surname: Mahdavi fullname: Mahdavi, Alborz – sequence: 3 givenname: Jennifer J. L surname: Hodas fullname: Hodas, Jennifer J. L – sequence: 4 givenname: John D surname: Bagert fullname: Bagert, John D – sequence: 5 givenname: John T surname: Ngo fullname: Ngo, John T – sequence: 6 givenname: Peter surname: Landgraf fullname: Landgraf, Peter – sequence: 7 givenname: Daniela C surname: Dieterich fullname: Dieterich, Daniela C – sequence: 8 givenname: Erin M surname: Schuman fullname: Schuman, Erin M – sequence: 9 givenname: David A surname: Tirrell fullname: Tirrell, David A email: tirrell@caltech.edu |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/21141861$$D View this record in MEDLINE/PubMed |
| BookMark | eNqNks2OFCEUhYkZ4_SMLnwBUxtjJqYcoCgKNiZtxb-kE104a0JRt0ZaGkaoatPzBK59RJ9EKt121MzCFZD7nXPhXM7QiQ8eEHpM8AuCKblca4JFJbG8hxakprisCeUnaIExpmUjeHWKzlJa5yOjgjxAp5QQRgQnC3TVOtBb3TkoXtkwWl98jKGDVAwhFivdgbP-ugjDXN0EB2Zyubi1ulje2h5-fv-xdF92Hop2Z1zQfW9HG_xDdH_QLsGjw3qOrt68_tS-K1cf3r5vl6tSV1yOpdQdxwIGIxvBOG-amkrDKiZM1UswTDPRSwkY14KQWhiCuwFYR4nktDeSVefo5d73Zuo20BvwY9RO3US70XGngrbq74q3n9V12KoKE45rnA2eHQxi-DpBGtXGJgPOaQ9hSkrkpCTFTGTyyZ-tjj1-R5mB53vgG3RhSMaCN3DE5lGI_AzR5F0931z8P93aUc-xtmHyY5Ze7KUmhpQiDEcZwWr-D-r4HzJ7-Q9rDl45DuvuVDzdK7RJah2m6PMA7-B-AYzNwRw |
| CitedBy_id | crossref_primary_10_1038_s41467_018_03511_6 crossref_primary_10_1021_jacs_4c02278 crossref_primary_10_1039_C7MB00491E crossref_primary_10_1039_C8MO00089A crossref_primary_10_1016_j_cclet_2021_03_016 crossref_primary_10_1021_jacs_0c04121 crossref_primary_10_1016_j_tetlet_2020_152018 crossref_primary_10_1021_acs_bioconjchem_7b00321 crossref_primary_10_1371_journal_pone_0154237 crossref_primary_10_1002_anie_202003478 crossref_primary_10_1021_acsinfecdis_6b00084 crossref_primary_10_1016_j_bmc_2024_117663 crossref_primary_10_1002_cmdc_201200498 crossref_primary_10_1007_s10439_013_0878_3 crossref_primary_10_1002_anie_201913620 crossref_primary_10_1016_j_tips_2024_09_001 crossref_primary_10_1016_j_biocel_2022_106289 crossref_primary_10_1021_jacs_6b06003 crossref_primary_10_1016_j_cbpa_2013_07_021 crossref_primary_10_1016_j_cbpa_2012_11_007 crossref_primary_10_1039_C2OB26561C crossref_primary_10_1021_acs_jproteome_3c00179 crossref_primary_10_1021_acs_analchem_9b04937 crossref_primary_10_1039_C5OB01056J crossref_primary_10_1038_nmeth_2401 crossref_primary_10_1039_c1ob06123b crossref_primary_10_1039_C9CC00055K crossref_primary_10_1021_acschembio_9b00424 crossref_primary_10_1039_D3SC02868B crossref_primary_10_1039_D3CB00042G crossref_primary_10_1073_pnas_1514412113 crossref_primary_10_1016_j_snb_2022_132167 crossref_primary_10_1002_asia_201100306 crossref_primary_10_1021_cr200338q crossref_primary_10_1021_ac202637n crossref_primary_10_1016_j_bbagen_2013_05_040 crossref_primary_10_1002_hlca_202400031 crossref_primary_10_1039_c2cc31887c crossref_primary_10_1016_j_chembiol_2023_09_009 crossref_primary_10_1016_j_cbpa_2020_09_001 crossref_primary_10_1021_cb400704n crossref_primary_10_1021_jacs_4c01402 crossref_primary_10_1021_acs_analchem_8b02426 crossref_primary_10_1016_j_bios_2020_112215 crossref_primary_10_1002_9780470559277_ch150185 crossref_primary_10_1021_acs_chemrev_0c00884 crossref_primary_10_1021_ar200144y crossref_primary_10_12677_AAC_2022_122014 crossref_primary_10_1016_j_chroma_2020_461051 crossref_primary_10_1002_anie_201912075 crossref_primary_10_3762_bjoc_20_199 crossref_primary_10_1021_acschembio_9b00511 crossref_primary_10_1016_j_foodchem_2023_136997 crossref_primary_10_1016_j_jcoa_2024_100154 crossref_primary_10_1073_pnas_1301740111 crossref_primary_10_1021_mz5004097 crossref_primary_10_1039_D2SC00918H crossref_primary_10_1039_C5SC03340C crossref_primary_10_1038_ncomms5776 crossref_primary_10_1002_ijch_202200100 crossref_primary_10_1016_j_chembiol_2016_05_018 crossref_primary_10_1002_ange_201302278 crossref_primary_10_1016_j_jtbi_2018_10_046 crossref_primary_10_1002_ange_202003478 crossref_primary_10_1021_acs_bioconjchem_4c00423 crossref_primary_10_1021_acschembio_8b00414 crossref_primary_10_1002_pmic_201800433 crossref_primary_10_1016_j_cbpa_2016_12_026 crossref_primary_10_1039_c3cc42214c crossref_primary_10_1021_acs_bioconjchem_6b00556 crossref_primary_10_1002_chem_202301067 crossref_primary_10_1002_open_202000128 crossref_primary_10_6023_A23050263 crossref_primary_10_1002_ange_201912075 crossref_primary_10_1021_acs_chemrev_0c01282 crossref_primary_10_1038_srep07896 crossref_primary_10_1002_cbic_202300082 crossref_primary_10_1039_C5OB00505A crossref_primary_10_1002_cbic_201700214 crossref_primary_10_1039_C7CC05814D crossref_primary_10_1016_j_bmc_2016_01_050 crossref_primary_10_1021_jacs_8b01462 crossref_primary_10_1016_j_cell_2014_11_051 crossref_primary_10_1039_c2ra20082a crossref_primary_10_1038_nmeth_3366 crossref_primary_10_1021_jacs_2c01528 crossref_primary_10_1038_s41557_019_0352_4 crossref_primary_10_1126_science_aal3316 crossref_primary_10_1021_acschembio_1c00981 crossref_primary_10_1002_anie_201302278 crossref_primary_10_1002_cbic_201300396 crossref_primary_10_1074_mcp_M112_021014 crossref_primary_10_1021_jacs_9b01164 crossref_primary_10_1002_ange_202315085 crossref_primary_10_1039_C5OB00488H crossref_primary_10_1002_cmdc_201200057 crossref_primary_10_1038_s41598_018_29126_x crossref_primary_10_1039_C7CC08605A crossref_primary_10_1021_cb300238w crossref_primary_10_4155_bio_14_239 crossref_primary_10_1039_c2cc18160f crossref_primary_10_1021_jacs_2c11858 crossref_primary_10_3389_fchem_2021_761609 crossref_primary_10_1021_acschembio_7b01023 crossref_primary_10_1016_j_cbpa_2021_07_001 crossref_primary_10_1016_j_jnutbio_2019_108286 crossref_primary_10_1021_jacs_1c10536 crossref_primary_10_1016_j_bmc_2017_09_014 crossref_primary_10_1021_jacs_9b11746 crossref_primary_10_1039_D0MO00181C crossref_primary_10_1002_chem_201400056 crossref_primary_10_1038_nmeth_4465 crossref_primary_10_1039_c3cc42076k crossref_primary_10_1039_D3AN02059B crossref_primary_10_1038_nprot_2012_010 crossref_primary_10_1021_jasms_0c00116 crossref_primary_10_1039_C4CC05246C crossref_primary_10_1111_1462_2920_12436 crossref_primary_10_1007_s00216_016_9934_9 crossref_primary_10_1021_acs_jproteome_1c00473 crossref_primary_10_1016_j_tet_2023_133554 crossref_primary_10_1039_D4OB02015D crossref_primary_10_1371_journal_pone_0099346 crossref_primary_10_1016_j_bmcl_2011_04_115 crossref_primary_10_1002_ange_201913620 crossref_primary_10_1016_j_jtbi_2017_03_031 crossref_primary_10_1021_jacs_3c05797 crossref_primary_10_1021_acs_biochem_7b01038 crossref_primary_10_1093_bioinformatics_btv558 crossref_primary_10_1016_j_cbpa_2019_11_003 crossref_primary_10_1021_acs_analchem_9b01873 crossref_primary_10_1021_jasms_1c00079 crossref_primary_10_1016_j_bmcl_2021_128244 crossref_primary_10_1016_j_cbpa_2024_102460 crossref_primary_10_1016_j_chembiol_2016_12_006 crossref_primary_10_1021_acsomega_8b01209 crossref_primary_10_3389_fchem_2021_737093 crossref_primary_10_1002_cpch_75 crossref_primary_10_3390_ijms23042365 crossref_primary_10_1039_D3CB00097D crossref_primary_10_1074_mcp_R120_002190 crossref_primary_10_1021_acs_jproteome_8b00986 crossref_primary_10_1021_acs_jproteome_2c00174 crossref_primary_10_1038_s43586_024_00308_4 crossref_primary_10_1002_anie_201711710 crossref_primary_10_1021_acschembio_6b01065 crossref_primary_10_1074_jbc_M116_736975 crossref_primary_10_1021_jacs_1c11053 crossref_primary_10_1073_pnas_1216375110 crossref_primary_10_1039_c2ob25440a crossref_primary_10_1002_anie_201708790 crossref_primary_10_1016_j_jchromb_2021_122527 crossref_primary_10_1038_s41596_018_0106_6 crossref_primary_10_1021_ar200125k crossref_primary_10_1021_acs_analchem_1c05438 crossref_primary_10_1002_pmic_201200112 crossref_primary_10_1186_s12864_015_2299_1 crossref_primary_10_1002_cbic_202400852 crossref_primary_10_1016_j_bmc_2011_07_048 crossref_primary_10_1021_jacs_4c03632 crossref_primary_10_1039_C9OB02515D crossref_primary_10_1038_nprot_2015_062 crossref_primary_10_1039_c3mb00003f crossref_primary_10_1002_ange_201711710 crossref_primary_10_1038_s41589_025_01849_9 crossref_primary_10_1074_mcp_M113_031914 crossref_primary_10_3390_pharmaceutics14010072 crossref_primary_10_1021_acs_joc_1c03027 crossref_primary_10_1002_anie_202315085 crossref_primary_10_1038_s41557_023_01281_3 crossref_primary_10_1038_nbt_4016 crossref_primary_10_1021_bc400093x crossref_primary_10_1039_C6MB00138F crossref_primary_10_1002_9780470559277_ch120241 crossref_primary_10_1002_ange_201708790 |
| Cites_doi | 10.1002/anie.201002050 10.1038/86783 10.1021/cb900085z 10.1002/anie.200905087 10.1021/cr980040+ 10.1021/jo011148j 10.1021/jo00246a038 10.1021/bc0503059 10.1021/ja064619y 10.1074/mcp.M700124-MCP200 10.1002/anie.200603811 10.1073/pnas.92.16.7590 10.1021/ja992749j 10.1021/cb6003228 10.1016/S0040-4020(01)92229-X 10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4 10.1002/anie.200700779 10.1038/nprot.2007.268 10.1021/bi00534a024 10.1074/mcp.M900121-MCP200 10.1073/pnas.012583299 10.1073/pnas.0605418103 10.1073/pnas.0712168105 10.1073/pnas.82.9.2593 10.1016/0003-2697(70)90102-8 10.1021/ja810122f 10.1016/j.chembiol.2009.06.005 10.1021/ja034490h 10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5 10.1073/pnas.81.17.5286 10.1073/pnas.0601637103 10.1074/jbc.M202508200 10.1038/nchembio.200 10.1038/nprot.2007.52 |
| ContentType | Journal Article |
| Copyright | Copyright © 2010 American Chemical Society |
| Copyright_xml | – notice: Copyright © 2010 American Chemical Society |
| DBID | AAYXX CITATION 17B 1KM BLEPL DTL EGQ GIGBA CGR CUY CVF ECM EIF NPM 7X8 5PM |
| DOI | 10.1021/ja1083909 |
| DatabaseName | CrossRef Web of Knowledge Index Chemicus Web of Science Core Collection Science Citation Index Expanded Web of Science Primary (SCIE, SSCI & AHCI) Web of Science - Science Citation Index Expanded - 2010 Medline MEDLINE MEDLINE (Ovid) MEDLINE MEDLINE PubMed MEDLINE - Academic PubMed Central (Full Participant titles) |
| DatabaseTitle | CrossRef Web of Science MEDLINE Medline Complete MEDLINE with Full Text PubMed MEDLINE (Ovid) MEDLINE - Academic |
| DatabaseTitleList | MEDLINE - Academic Web of Science MEDLINE |
| Database_xml | – sequence: 1 dbid: NPM name: PubMed url: https://proxy.k.utb.cz/login?url=http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed sourceTypes: Index Database – sequence: 2 dbid: 1KM name: Index Chemicus url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/woscc/search-with-editions?editions=WOS.IC sourceTypes: Enrichment Source Index Database |
| DeliveryMethod | fulltext_linktorsrc |
| Discipline | Chemistry |
| DocumentTitleAlternate | Cleavable Biotin Probes |
| EISSN | 1520-5126 |
| EndPage | 18360 |
| ExternalDocumentID | PMC3016050 21141861 000285818700054 10_1021_ja1083909 c101324672 |
| Genre | Research Support, U.S. Gov't, Non-P.H.S Research Support, Non-U.S. Gov't Journal Article Research Support, N.I.H., Extramural |
| GrantInformation_xml | – fundername: NIH; United States Department of Health & Human Services; National Institutes of Health (NIH) - USA grantid: GM62523; MH065537 – fundername: National Science and Engineering Council of Canada (NSERC); Natural Sciences and Engineering Research Council of Canada (NSERC) – fundername: ARO Institute for Collaborative Biotechnologies – fundername: Fonds Quebecois de la Recherche sur la Nature et les Technologies; Fonds de recherche du Quebec (FRQ); Fonds de recherche du Quebec - Nature et technologies (FRQNT) – fundername: NIMH NIH HHS grantid: R01 MH065537 – fundername: NIGMS NIH HHS grantid: GM62523 – fundername: NIGMS NIH HHS grantid: R01 GM062523 – fundername: NIMH NIH HHS grantid: MH065537 |
| GroupedDBID | - .K2 02 4.4 53G 55A 5GY 5RE 5VS 7~N 85S AABXI ABFLS ABMVS ABPPZ ABPTK ABUCX ABUFD ACGFS ACJ ACNCT ACS AEESW AENEX AETEA AFEFF AFFNX ALMA_UNASSIGNED_HOLDINGS AQSVZ BAANH BKOMP CS3 DU5 DZ EBS ED ED~ EJD ET F5P GNL IH9 JG JG~ K2 LG6 P2P ROL RXW TAE TAF TN5 UHB UI2 UKR UPT VF5 VG9 VQA W1F WH7 X XFK YZZ ZHY --- -DZ -ET -~X .DC AAHBH AAYOK AAYXX ABBLG ABJNI ABLBI ABQRX ACBEA ACGFO ADHLV AGXLV AHDLI AHGAQ CITATION CUPRZ GGK IH2 XSW YQT ZCA ~02 17B 1KM AAYWT BLEPL DTL GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED GROUPED_WOS_WEB_OF_SCIENCE CGR CUY CVF ECM EIF NPM 7X8 5PM |
| ID | FETCH-LOGICAL-a369t-9ab608efc97846677529c4348c3d9ec4a48d99e00581158c10bfe4b21962dc943 |
| IEDL.DBID | ACS |
| ISICitedReferencesCount | 180 |
| ISICitedReferencesURI | https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=000285818700054 |
| ISSN | 0002-7863 1520-5126 |
| IngestDate | Thu Aug 21 18:17:04 EDT 2025 Mon Jul 21 09:43:23 EDT 2025 Mon Jul 21 06:06:50 EDT 2025 Wed Aug 06 11:23:38 EDT 2025 Fri Aug 29 16:17:30 EDT 2025 Tue Jul 01 02:07:58 EDT 2025 Thu Apr 24 23:03:20 EDT 2025 Thu Aug 27 13:42:54 EDT 2020 |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 51 |
| Keywords | REPORTER ANALOGS RECOMBINANT PROTEINS IN-VIVO SOLID-PHASE CHEMISTRY LIGATION TERMINAL ALKYNES IDENTIFICATION PROTEOMES |
| Language | English |
| LinkModel | DirectLink |
| LogoURL | https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg |
| MergedId | FETCHMERGED-LOGICAL-a369t-9ab608efc97846677529c4348c3d9ec4a48d99e00581158c10bfe4b21962dc943 |
| Notes | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
| ORCID | 0000-0002-9880-1214 0000-0003-3508-1915 |
| PMID | 21141861 |
| PQID | 821192048 |
| PQPubID | 23479 |
| PageCount | 10 |
| ParticipantIDs | acs_journals_10_1021_ja1083909 webofscience_primary_000285818700054 crossref_primary_10_1021_ja1083909 proquest_miscellaneous_821192048 pubmedcentral_primary_oai_pubmedcentral_nih_gov_3016050 pubmed_primary_21141861 webofscience_primary_000285818700054CitationCount crossref_citationtrail_10_1021_ja1083909 |
| ProviderPackageCode | JG~ 55A AABXI GNL VF5 7~N ACJ VG9 W1F ACS AEESW AFEFF .K2 ABMVS ABUCX IH9 BAANH AQSVZ ED~ UI2 CITATION AAYXX |
| PublicationCentury | 2000 |
| PublicationDate | 2010-12-29 |
| PublicationDateYYYYMMDD | 2010-12-29 |
| PublicationDate_xml | – month: 12 year: 2010 text: 2010-12-29 day: 29 |
| PublicationDecade | 2010 |
| PublicationPlace | WASHINGTON |
| PublicationPlace_xml | – name: WASHINGTON – name: United States |
| PublicationTitle | Journal of the American Chemical Society |
| PublicationTitleAbbrev | J AM CHEM SOC |
| PublicationTitleAlternate | J. Am. Chem. Soc |
| PublicationYear | 2010 |
| Publisher | American Chemical Society Amer Chemical Soc |
| Publisher_xml | – name: American Chemical Society – name: Amer Chemical Soc |
| References | Wuts P. G. M. (ref26/cit26) 2007 Hannoush R. N. (ref8/cit8) 2009; 4 Oda Y. (ref18/cit18) 2001; 19 Gololobov Y. G. (ref28/cit28) 1992; 48 Tornoe C. W. (ref3/cit3) 2002; 67 Sawa M. (ref7/cit7) 2006; 103 Leighton B. H. (ref16/cit16) 2002; 277 Gillard J. W. (ref29/cit29) 1988; 53 Dieterich D. C. (ref4/cit4) 2006; 103 Van Hest J. C. M. (ref12/cit12) 2000; 122 Merel A. (ref22/cit22b) 2009; 8 Dieterich D. C. (ref17/cit17) 2007; 2 Rostovtsev V. V. (ref2/cit2) 2002; 41 Charron G. (ref9/cit9) 2009; 131 Salic A. (ref10/cit10) 2008; 105 McCormick D. B. (ref33/cit33) 1970; 34 Shimkus M. (ref22/cit22a) 1985; 82 Agard N. J. (ref13/cit13) 2006; 1 Kiick K. L. (ref11/cit11a) 2002; 99 Link A. J. (ref11/cit11b) 2007; 2 Hofmann K. (ref20/cit20) 1982; 21 Denny J. B. (ref30/cit30) 1984; 81 Yoo T. H. (ref31/cit31) 2007; 46 Grammel M. (ref15/cit15) 2010; 49 Olejnik J. (ref24/cit24a) 1995; 92 Ngo J. T. (ref14/cit14) 2009; 5 Park K. D. (ref25/cit25) 2009; 16 Hong V. (ref32/cit32) 2009; 48 Speers A. E. (ref5/cit5) 2003; 125 Guillier F. (ref27/cit27) 2000; 100 Rabuka D. (ref6/cit6) 2006; 128 Fonovic M. (ref19/cit19) 2007; 6 Verhelst S. H. L. (ref23/cit23) 2007; 46 Kim H. H. (ref24/cit24b) 2009; 8 Kolb H. C. (ref1/cit1) 2001; 40 Fauq A. H. (ref21/cit21) 2006; 17 Leighton, BH (WOS:000177509300064) 2002; 277 Charron, G (WOS:000264806300072) 2009; 131 DENNY, JB (WOS:A1984TK56500002) 1984; 81 Agard, NJ (WOS:000243895200017) 2006; 1 Rostovtsev, VV (WOS:000176972000038) 2002; 41 Rabuka, D (WOS:000240465200023) 2006; 128 GILLARD, JW (WOS:A1988N641300038) 1988; 53 Kiick, KL (WOS:000173233300006) 2002; 99 Wuts,, P. G. M. (000285818700054.35) 2007 Yoo, TH (WOS:000248063200017) 2007; 46 Merel,, A. (000285818700054.21) 2009; 8 Hong, V (WOS:000273452200020) 2009; 48 Fonovic, M (WOS:000250092600009) 2007; 6 Verhelst, SHL (WOS:000244382200017) 2007; 46 Dieterich, DC (WOS:000253138200010) 2007; 2 Kolb, HC (WOS:000169168100001) 2001; 40 van Hest, JCM (WOS:000085639200005) 2000; 122 GOLOLOBOV, YG (WOS:A1992HE90300001) 1992; 48 Speers, AE (WOS:000182331800008) 2003; 125 Kim, HYH (WOS:000269752800006) 2009; 8 Park, KD (WOS:000268762300010) 2009; 16 SHIMKUS, M (WOS:A1985AGW3200009) 1985; 82 Salic, A (WOS:000253469900032) 2008; 105 HOFMANN, K (WOS:A1982NE31400024) 1982; 21 Tornoe, CW (WOS:000175323600045) 2002; 67 Oda, Y (WOS:000167940700030) 2001; 19 Guillier, F (WOS:000087778100007) 2000; 100 Dieterich, DC (WOS:000238660400020) 2006; 103 Ngo, JT (WOS:000270039900006) 2009; 5 Link, AJ (WOS:000253139400005) 2007; 2 OLEJNIK, J (WOS:A1995RM72200093) 1995; 92 MCCORMICK, DB (WOS:A1970G075100024) 1970; 34 Hannoush, RN (WOS:000268233000010) 2009; 4 Sawa, M (WOS:000239867500032) 2006; 103 Grammel, M (WOS:000281105600030) 2010; 49 Fauq, AH (WOS:000234905500034) 2006; 17 |
| References_xml | – volume: 49 start-page: 5970 year: 2010 ident: ref15/cit15 publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.201002050 – volume: 19 start-page: 379 year: 2001 ident: ref18/cit18 publication-title: Nat. Biotechnol. doi: 10.1038/86783 – volume: 4 start-page: 581 year: 2009 ident: ref8/cit8 publication-title: ACS Chem. Biol. doi: 10.1021/cb900085z – volume: 48 start-page: 9879 year: 2009 ident: ref32/cit32 publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.200905087 – volume: 100 start-page: 2091 year: 2000 ident: ref27/cit27 publication-title: Chem. Rev. doi: 10.1021/cr980040+ – volume: 67 start-page: 3057 year: 2002 ident: ref3/cit3 publication-title: J. Org. Chem. doi: 10.1021/jo011148j – volume: 53 start-page: 2602 year: 1988 ident: ref29/cit29 publication-title: J. Org. Chem. doi: 10.1021/jo00246a038 – volume: 17 start-page: 248 year: 2006 ident: ref21/cit21 publication-title: Bioconjugate Chem. doi: 10.1021/bc0503059 – volume: 128 start-page: 12078 year: 2006 ident: ref6/cit6 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja064619y – volume: 6 start-page: 1761 year: 2007 ident: ref19/cit19 publication-title: Mol. Cell. Proteomics doi: 10.1074/mcp.M700124-MCP200 – volume: 46 start-page: 1284 year: 2007 ident: ref23/cit23 publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.200603811 – volume: 92 start-page: 7590 year: 1995 ident: ref24/cit24a publication-title: Proc. Natl. Acad. Sci. U.S.A. doi: 10.1073/pnas.92.16.7590 – volume: 122 start-page: 1282 year: 2000 ident: ref12/cit12 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja992749j – volume: 1 start-page: 644 year: 2006 ident: ref13/cit13 publication-title: ACS Chem. Biol. doi: 10.1021/cb6003228 – volume: 48 start-page: 1353 year: 1992 ident: ref28/cit28 publication-title: Tetrahedron doi: 10.1016/S0040-4020(01)92229-X – volume: 41 start-page: 2596 year: 2002 ident: ref2/cit2 publication-title: Angew. Chem., Int. Ed. doi: 10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4 – volume: 46 start-page: 5340 year: 2007 ident: ref31/cit31 publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.200700779 – volume: 2 start-page: 1879 year: 2007 ident: ref11/cit11b publication-title: Nat. Prot. doi: 10.1038/nprot.2007.268 – volume: 21 start-page: 978 year: 1982 ident: ref20/cit20 publication-title: Biochemistry doi: 10.1021/bi00534a024 – volume: 8 start-page: 2080 year: 2009 ident: ref24/cit24b publication-title: Mol. Cell. Proteomics doi: 10.1074/mcp.M900121-MCP200 – volume: 99 start-page: 19 year: 2002 ident: ref11/cit11a publication-title: Proc. Natl. Acad. Sci. U.S.A. doi: 10.1073/pnas.012583299 – volume: 103 start-page: 12371 year: 2006 ident: ref7/cit7 publication-title: Proc. Natl. Acad. Sci. U.S.A. doi: 10.1073/pnas.0605418103 – volume: 8 start-page: 3709 year: 2009 ident: ref22/cit22b publication-title: J. Proteome Res. – volume: 105 start-page: 2415 year: 2008 ident: ref10/cit10 publication-title: Proc. Natl. Acad. Sci. U.S.A. doi: 10.1073/pnas.0712168105 – volume: 82 start-page: 2593 year: 1985 ident: ref22/cit22a publication-title: Proc. Natl. Acad. Sci. U.S.A. doi: 10.1073/pnas.82.9.2593 – volume: 34 start-page: 226 year: 1970 ident: ref33/cit33 publication-title: Anal. Biochem. doi: 10.1016/0003-2697(70)90102-8 – volume: 131 start-page: 4967 year: 2009 ident: ref9/cit9 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja810122f – volume: 16 start-page: 763 year: 2009 ident: ref25/cit25 publication-title: Chem. Biol. doi: 10.1016/j.chembiol.2009.06.005 – volume: 125 start-page: 4686 year: 2003 ident: ref5/cit5 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja034490h – volume-title: Protective Groups in Organic Synthesis year: 2007 ident: ref26/cit26 – volume: 40 start-page: 2004 year: 2001 ident: ref1/cit1 publication-title: Angew. Chem., Int. Ed. doi: 10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5 – volume: 81 start-page: 5286 year: 1984 ident: ref30/cit30 publication-title: Proc. Natl. Acad. Sci. U.S.A. doi: 10.1073/pnas.81.17.5286 – volume: 103 start-page: 9482 year: 2006 ident: ref4/cit4 publication-title: Proc. Natl. Acad. Sci. U.S.A. doi: 10.1073/pnas.0601637103 – volume: 277 start-page: 29847 year: 2002 ident: ref16/cit16 publication-title: J. Biol. Chem. doi: 10.1074/jbc.M202508200 – volume: 5 start-page: 715 year: 2009 ident: ref14/cit14 publication-title: Nat. Chem. Biol. doi: 10.1038/nchembio.200 – volume: 2 start-page: 532 year: 2007 ident: ref17/cit17 publication-title: Nat. Protoc. doi: 10.1038/nprot.2007.52 – volume: 19 start-page: 379 year: 2001 ident: WOS:000167940700030 article-title: Enrichment analysis of phosphorylated proteins as a tool for probing the phosphoproteome publication-title: NATURE BIOTECHNOLOGY – volume: 49 start-page: 5970 year: 2010 ident: WOS:000281105600030 article-title: Orthogonal Alkynyl Amino Acid Reporter for Selective Labeling of Bacterial Proteomes during Infection publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201002050 – volume: 128 start-page: 12078 year: 2006 ident: WOS:000240465200023 article-title: A chemical reporter strategy to probe glycoprotein fucosylation publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja064619y – volume: 100 start-page: 2091 year: 2000 ident: WOS:000087778100007 article-title: Linkers and cleavage strategies in solid-phase organic synthesis and combinatorial chemistry publication-title: CHEMICAL REVIEWS doi: 10.1021/cr980040+ – volume: 41 start-page: 2596 year: 2002 ident: WOS:000176972000038 article-title: A stepwise Huisgen cycloaddition process: Copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION – volume: 81 start-page: 5286 year: 1984 ident: WOS:A1984TK56500002 article-title: I-125-LABELED CROSSLINKING REAGENT THAT IS HYDROPHILIC, PHOTOACTIVATABLE, AND CLEAVABLE THROUGH AN AZO LINKAGE publication-title: PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA-BIOLOGICAL SCIENCES – volume: 6 start-page: 1761 year: 2007 ident: WOS:000250092600009 article-title: Proteomics evaluation of chemically cleavable activity-based probes publication-title: MOLECULAR & CELLULAR PROTEOMICS doi: 10.1074/mcp.M700124-MCP200 – volume: 17 start-page: 248 year: 2006 ident: WOS:000234905500034 article-title: Synthesis of acid-cleavable light isotope-coded affinity tags (ICAT-L) for potential use in proteomic expression profiling analysis publication-title: BIOCONJUGATE CHEMISTRY doi: 10.1021/bc0503059 – volume: 5 start-page: 715 year: 2009 ident: WOS:000270039900006 article-title: Cell-selective metabolic labeling of proteins publication-title: NATURE CHEMICAL BIOLOGY doi: 10.1038/nchembio.200 – volume: 99 start-page: 19 year: 2002 ident: WOS:000173233300006 article-title: Incorporation of azides into recombinant proteins for chemoselective modification by the Staudinger ligation publication-title: PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA – volume: 92 start-page: 7590 year: 1995 ident: WOS:A1995RM72200093 article-title: PHOTOCLEAVABLE BIOTIN DERIVATIVES - A VERSATILE APPROACH FOR THE ISOLATION OF BIOMOLECULES publication-title: PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA – volume: 122 start-page: 1282 year: 2000 ident: WOS:000085639200005 article-title: Efficient incorporation of unsaturated methionine analogues into proteins in vivo publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY – volume: 4 start-page: 581 year: 2009 ident: WOS:000268233000010 article-title: Imaging the Lipidome: ω-Alkynyl Fatty Acids for Detection and Cellular Visualization of Lipid-Modified Proteins publication-title: ACS CHEMICAL BIOLOGY doi: 10.1021/cb900085z – volume: 103 start-page: 12371 year: 2006 ident: WOS:000239867500032 article-title: Glycoproteomic probes for fluorescent imaging of fucosylated glycans in vivo publication-title: PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA doi: 10.1073/pnas.0605418103 – volume: 82 start-page: 2593 year: 1985 ident: WOS:A1985AGW3200009 article-title: A CHEMICALLY CLEAVABLE BIOTINYLATED NUCLEOTIDE - USEFULNESS IN THE RECOVERY OF PROTEIN DNA COMPLEXES FROM AVIDIN AFFINITY COLUMNS publication-title: PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA – volume: 53 start-page: 2602 year: 1988 ident: WOS:A1988N641300038 article-title: SYMMETRICAL ALKOXYSILYL ETHERS - A NEW CLASS OF ALCOHOL-PROTECTING GROUPS - PREPARATION OF TERT-BUTOXYDIPHENYLSILYL ETHERS publication-title: JOURNAL OF ORGANIC CHEMISTRY – volume: 48 start-page: 1353 year: 1992 ident: WOS:A1992HE90300001 article-title: RECENT ADVANCES IN THE STAUDINGER REACTION publication-title: TETRAHEDRON – volume: 105 start-page: 2415 year: 2008 ident: WOS:000253469900032 article-title: A chemical method for fast and sensitive detection of DNA synthesis in vivo publication-title: PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA doi: 10.1073/pnas.0712168105 – volume: 46 start-page: 5340 year: 2007 ident: WOS:000248063200017 article-title: High-throughput screening for Methionyl-tRNA synthetases that enable residue-specific incorporation of noncanonical amino acids into recombinant proteins in bacterial cells publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200700779 – volume: 125 start-page: 4686 year: 2003 ident: WOS:000182331800008 article-title: Activity-based protein profiling in vivo using a copper(I)-catalyzed azide-alkyne [3+2] cycloaddition publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja034490h – volume: 131 start-page: 4967 year: 2009 ident: WOS:000264806300072 article-title: Robust Fluorescent Detection of Protein Fatty-Acylation with Chemical Reporters publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja810122f – volume: 67 start-page: 3057 year: 2002 ident: WOS:000175323600045 article-title: Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo011148j – volume: 48 start-page: 9879 year: 2009 ident: WOS:000273452200020 article-title: Analysis and Optimization of Copper-Catalyzed Azide-Alkyne Cycloaddition for Bioconjugation publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200905087 – volume: 8 start-page: 3709 year: 2009 ident: 000285818700054.21 publication-title: J. Proteome Res. – volume: 277 start-page: 29847 year: 2002 ident: WOS:000177509300064 article-title: A hydrophobic domain in glutamate transporters forms an extracellular helix associated with the permeation pathway for substrates publication-title: JOURNAL OF BIOLOGICAL CHEMISTRY doi: 10.1074/jbc.M202508200 – volume: 8 start-page: 2080 year: 2009 ident: WOS:000269752800006 article-title: An Azido-Biotin Reagent for Use in the Isolation of Protein Adducts of Lipid-derived Electrophiles by Streptavidin Catch and Photorelease publication-title: MOLECULAR & CELLULAR PROTEOMICS doi: 10.1074/mcp.M900121-MCP200 – volume: 21 start-page: 978 year: 1982 ident: WOS:A1982NE31400024 article-title: AVIDIN BINDING OF CARBOXYL-SUBSTITUTED BIOTIN AND ANALOGS publication-title: BIOCHEMISTRY – volume: 40 start-page: 2004 year: 2001 ident: WOS:000169168100001 article-title: Click chemistry: Diverse chemical function from a few good reactions publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION – volume: 2 start-page: 1879 year: 2007 ident: WOS:000253139400005 article-title: Preparation of the functionalizable methionine surrogate azidohomoalanine via copper-catalyzed diazo transfer publication-title: NATURE PROTOCOLS doi: 10.1038/nprot.2007.268 – volume: 1 start-page: 644 year: 2006 ident: WOS:000243895200017 article-title: A comparative study of bioorthogonal reactions with azides publication-title: ACS CHEMICAL BIOLOGY doi: 10.1021/cb6003228 – volume: 16 start-page: 763 year: 2009 ident: WOS:000268762300010 article-title: Useful Tools for Biomolecule Isolation, Detection, and Identification: Acylhydrazone-Based Cleavable Linkers publication-title: CHEMISTRY & BIOLOGY doi: 10.1016/j.chembiol.2009.06.005 – volume: 2 start-page: 532 year: 2007 ident: WOS:000253138200010 article-title: Labeling, detection and identification of newly synthesized proteomes with bioorthogonal non-canonical amino-acid tagging publication-title: NATURE PROTOCOLS doi: 10.1038/nprot.2007.52 – volume: 46 start-page: 1284 year: 2007 ident: WOS:000244382200017 article-title: A mild chemically cleavable linker system for functional proteomic applications publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200603811 – volume: 34 start-page: 226 year: 1970 ident: WOS:A1970G075100024 article-title: SPECIFICITY, STEREOCHEMISTRY, AND MECHANISM OF COLOR REACTION BETWEEN PARA-DIMETHYLAMINOCINNAMALDEHYDE AND BIOTIN ANALOGS publication-title: ANALYTICAL BIOCHEMISTRY – volume: 103 start-page: 9482 year: 2006 ident: WOS:000238660400020 article-title: Selective identification of newly synthesized proteins in mammalian cells using bioorthogonal noncanonical amino acid tagging (BONCAT) publication-title: PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA – year: 2007 ident: 000285818700054.35 publication-title: Protective Groups in Organic Synthesis |
| SSID | ssj0004281 |
| Score | 2.4382029 |
| Snippet | The azide−alkyne cycloaddition provides a powerful tool for bio-orthogonal labeling of proteins, nucleic acids, glycans, and lipids. In some labeling... The azide-alkyne cycloaddition provides a powerful tool for bio-orthogonal labeling of proteins, nucleic acids, glycans, and lipids. In some labeling... |
| Source | Web of Science |
| SourceID | pubmedcentral proquest pubmed webofscience crossref acs |
| SourceType | Open Access Repository Aggregation Database Index Database Enrichment Source Publisher |
| StartPage | 18351 |
| SubjectTerms | Alkynes - chemistry Azides - chemistry Biotin - chemistry Chemistry Chemistry, Multidisciplinary Cyclization Dapsone Green Fluorescent Proteins - chemistry Molecular Probes - chemical synthesis Molecular Probes - chemistry Physical Sciences Protein Structure, Secondary Proteins - chemistry Science & Technology |
| Title | Cleavable Biotin Probes for Labeling of Biomolecules via Azide−Alkyne Cycloaddition |
| URI | http://dx.doi.org/10.1021/ja1083909 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000285818700054 https://www.ncbi.nlm.nih.gov/pubmed/21141861 https://www.proquest.com/docview/821192048 https://pubmed.ncbi.nlm.nih.gov/PMC3016050 |
| Volume | 132 |
| WOS | 000285818700054 |
| WOSCitedRecordID | wos000285818700054 |
| hasFullText | 1 |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV1Lb9QwEB5V5QAX3o_wqCzogUuqxHYc-7gEqgoBQoKVeoscxxFRlwSx2UrtL-DMT-SXMJPH0qXL4-xJpMyMPd_EM98A7KNVy4o7H0pR6VAmkQzRbzBxRWibmLLALIS6kd--U0dz-fo4Od6BZ3-4wefEDxQjTDDUpHeFK51ShjXLPvxqfuQ6njBuqpWY6IMuPkqhxy03Q88lPLm9LPK3UNSHncMb8HJq3hmqTU4OVl1x4M4vczn-7YtuwvURdrLZ4Ce3YMc3t-FqNk17uwPzbOHtKfVRsRd129UNe0-NQkuGoJa9sUXfts7ailY_DyN1cfG0tmx2Xpf-x7fvs8XJWeNZduYWLVUpkcXvwvzw1cfsKBxHLoRWKNOFxhYq0r5ymFxKpdI04cZJIbUTpfFOWqlLYzwNI0QoqV0cFZWXBR57ipfOSHEPdpu28Q-AIbDylYwLL6ISkziPqaj1pSACQ2Ft5APYQ5vk45ZZ5v1tOMdsZNJOAM8nc-VuJCynuRmLbaJP16JfBpaObUJssnmOyqWLEdv4drXMNdHcEYNxAPcHF1i_BVdkrFUcQLrhHGsBoufeXGnqTz1NtyDyviQKYP-iG60f7H9sohrxwCTcHED8P2LZqAhiLOge_kuFj-AaH8tvuHkMu93XlX-CIKor9vpN9BNcDxO_ |
| linkProvider | American Chemical Society |
| linkToHtml | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwzV3NbtQwEB6VcigX_n_CT7FQkbikSmwnax84LIFqS7cVEl2pt-A4joi6JIhki7ZPwJkjr8Lb8CSMs0naLSvBpRJnTyxnPM58E898A7CFu5pmVBuXs0y4PPC4i3aDgStC20CmCUYhthp5_yAcTfjbo-BoDX50tTC4iApnqppL_DN2AUsT5CNakJ5sEyj3zPwrhmfVy93XuJfPKd15cxiN3LaDgKtYKGtXqiT0hMk0xko8DAeDgErNGReapdJorrhIpTS2tx4iI6F9L8kMT_AUhzTVkjOc9wpcRdBDbWA3jN6f1VxS4XfQeiBC1rEWnV-q9Xi6WvZ4f8DY1dmYFzxg4-12bsDPXk9Nksvx9qxOtvXpBQrJ_1ORN-F6C7LJcHEqbsGaKW7DRtT1trsDk2hq1ImtGiOv8rLOC_LOlkVVBCE8GaukKdInZWZHPy0aCOPgSa7I8DRPza9v34fT43lhSDTX09LmZFn7vguTS3mre7BelIV5AARhpMm4nxjmpRiyGgy8lUmZpWtkSnnGgU3cjLj9QFRxc_dPMfbqdsOBF52VxLqlZ7ddQqarRJ_1op8XnCSrhEhnajEq114DqcKUsyoWltTP8jU7cH9hef0sOMJ9EfoODJZsshewZOTLI0X-sSElZ5aqMPAc2Dpvvf2DzW9cVCO6BxslOOD_i1jUKsLyM9QP_6bCp7AxOtwfx-Pdg71HcI22iUdUPob1-svMPEH4WCebzTkm8OGy7f03eCt0MA |
| linkToPdf | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwzV3NbtQwEB6VIgEX_qHhp1ioSFxSJbGTjQ8clpRVS0tVCVbqLTiOI6Juk4pki7ZPwJkH4FV4F56EmWwSumUluFTi7InljMeZb-KZbwA2cFfTzNPGFjwLbeE7wka7wcAVoa0v0wSjEKpGfrcfbI_F20P_cAW-d7UwuIgKZ6qaS3w61Sdp1jIMEFWQi4hBOrJNotw1sy8YolWvdrZwP1943ujNh2jbbrsI2IoHsralSgInNJnGeEkEwWDge1ILLkLNU2m0UCJMpTTUXw_RUahdJ8mMSPAkB16qpeA47xW4SteDFNwNo_e_6y690O3g9SAMeMdcdH6p5PV0tej1_oCyyzMyL3jBxuONbsGPXldNosvR5rRONvXZBRrJ_1eZt-FmC7bZcH467sCKKe7C9ajrcXcPxtHEqFOqHmOv87LOC3ZA5VEVQyjP9lTSFOuzMqPR43kjYRw8zRUbnuWp-fn123ByNCsMi2Z6UlJuFtn5fRhfyls9gNWiLMwaMISTJhNuYriTYuhqMABXJuVE28iVcowF67ghcfuhqOImB8DDGKzbDQtedpYS65amnbqFTJaJPu9FT-bcJMuEWGduMSqXroNUYcppFYdE7ke8zRY8nFtfPwuOCDcMXAsGC3bZCxAp-eJIkX9qyMk5URb6jgUb5y24f7D5nYtqRDdB0YIF7r-IRa0iiKehfvQ3FT6Dawdbo3hvZ3_3Mdzw2vwjTz6B1frz1DxFFFkn681RZvDxss39F8sodrM |
| openUrl | ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Cleavable+Biotin+Probes+for+Labeling+of+Biomolecules+via+the+Azide+%E2%80%93+Alkyne+Cycloaddition&rft.jtitle=Journal+of+the+American+Chemical+Society&rft.au=Szychowski%2C+Janek&rft.au=Mahdavi%2C+Alborz&rft.au=Hodas%2C+Jennifer+J.+L.&rft.au=Bagert%2C+John+D.&rft.date=2010-12-29&rft.issn=0002-7863&rft.eissn=1520-5126&rft.volume=132&rft.issue=51&rft.spage=18351&rft.epage=18360&rft_id=info:doi/10.1021%2Fja1083909&rft_id=info%3Apmid%2F21141861&rft.externalDocID=PMC3016050 |
| thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0002-7863&client=summon |
| thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0002-7863&client=summon |
| thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0002-7863&client=summon |