Conformational Selection in Glycomimetics: Human Galectin-1 Only Recognizes syn-Ψ-Type Conformations of β-1,3-Linked Lactose and Its C-Glycosyl Derivative
The human lectin galectin‐1 (hGal‐1) translates sugar signals, that is, β‐galactosides, into effects on the level of cells, for example, growth regulation, and has become a model for studying binding of biopharmaceutically relevant derivatives. Bound‐state conformations of Galβ‐C‐(1→3)‐Glcβ‐OMe (1)...
Saved in:
Published in | Chemistry : a European journal Vol. 19; no. 43; pp. 14581 - 14590 |
---|---|
Main Authors | , , , , , , , , , , |
Format | Journal Article |
Language | English |
Published |
Weinheim
WILEY-VCH Verlag
18.10.2013
WILEY‐VCH Verlag Wiley-VCH Verlag |
Subjects | |
Online Access | Get full text |
Cover
Loading…
Abstract | The human lectin galectin‐1 (hGal‐1) translates sugar signals, that is, β‐galactosides, into effects on the level of cells, for example, growth regulation, and has become a model for studying binding of biopharmaceutically relevant derivatives. Bound‐state conformations of Galβ‐C‐(1→3)‐Glcβ‐OMe (1) and its βGal‐(1→3)‐βGlc‐OMe disaccharide parent compound were studied by using NMR spectroscopy (transferred (TR)‐NOESY data), assisted by docking experiments and molecular dynamics (MD) simulations. The molecular recognition process involves a conformational selection event. Although free C‐glycoside access four distinct conformers in solution, hGal‐1 recognizes shape of a local minimum of compound 1, the syn‐Φ/syn‐Ψ conformer, not the structure at global minimum. MD simulations were run to explain, in structural terms, the observed geometry of the complex.
Trapping one conformer: Combination of transferred (TR)‐NOESY experiments, which include the bioactive conformation determination with molecular modeling, have enabled the explanation, in structural chemistry terms, of a conformational selection process in the recognition of C‐glycomimetics by a human galectin (see figure). |
---|---|
AbstractList | The human lectin galectin-1 (hGal-1) translates sugar signals, that is, β-galactosides, into effects on the level of cells, for example, growth regulation, and has become a model for studying binding of biopharmaceutically relevant derivatives. Bound-state conformations of Galβ-C-(1→3)-Glcβ-OMe (1) and its βGal-(1→3)-βGlc-OMe disaccharide parent compound were studied by using NMR spectroscopy (transferred (TR)-NOESY data), assisted by docking experiments and molecular dynamics (MD) simulations. The molecular recognition process involves a conformational selection event. Although free C-glycoside access four distinct conformers in solution, hGal-1 recognizes shape of a local minimum of compound 1, the syn-Φ/syn-Ψ conformer, not the structure at global minimum. MD simulations were run to explain, in structural terms, the observed geometry of the complex. The human lectin galectin-1 (hGal-1) translates sugar signals, that is, beta-galactosides, into effects on the level of cells, for example, growth regulation, and has become a model for studying binding of biopharmaceutically relevant derivatives. Bound-state conformations of Gal beta-C-(1 -> 3)-Glc beta-OMe (1) and its beta Gal-(1 -> 3)-beta Glc-OMe disaccharide parent compound were studied by using NMR spectroscopy (transferred (TR)-NOESY data), assisted by docking experiments and molecular dynamics (MD) simulations. The molecular recognition process involves a conformational selection event. Although free C-glycoside access four distinct conformers in solution, hGal-1 recognizes shape of a local minimum of compound 1, the syn-Phi/syn-Psi conformer, not the structure at global minimum. MD simulations were run to explain, in structural terms, the observed geometry of the complex The human lectin galectin‐1 (hGal‐1) translates sugar signals, that is, β‐galactosides, into effects on the level of cells, for example, growth regulation, and has become a model for studying binding of biopharmaceutically relevant derivatives. Bound‐state conformations of Galβ‐C‐(1→3)‐Glcβ‐OMe (1) and its βGal‐(1→3)‐βGlc‐OMe disaccharide parent compound were studied by using NMR spectroscopy (transferred (TR)‐NOESY data), assisted by docking experiments and molecular dynamics (MD) simulations. The molecular recognition process involves a conformational selection event. Although free C‐glycoside access four distinct conformers in solution, hGal‐1 recognizes shape of a local minimum of compound 1, the syn‐Φ/syn‐Ψ conformer, not the structure at global minimum. MD simulations were run to explain, in structural terms, the observed geometry of the complex. Trapping one conformer: Combination of transferred (TR)‐NOESY experiments, which include the bioactive conformation determination with molecular modeling, have enabled the explanation, in structural chemistry terms, of a conformational selection process in the recognition of C‐glycomimetics by a human galectin (see figure). Abstract The human lectin galectin‐1 (hGal‐1) translates sugar signals, that is, β‐galactosides, into effects on the level of cells, for example, growth regulation, and has become a model for studying binding of biopharmaceutically relevant derivatives. Bound‐state conformations of Galβ‐ C ‐(1→3)‐Glcβ‐ O Me ( 1 ) and its βGal‐(1→3)‐βGlc‐OMe disaccharide parent compound were studied by using NMR spectroscopy (transferred (TR)‐NOESY data), assisted by docking experiments and molecular dynamics (MD) simulations. The molecular recognition process involves a conformational selection event. Although free C ‐glycoside access four distinct conformers in solution, hGal‐1 recognizes shape of a local minimum of compound 1 , the syn ‐ Φ / syn ‐ Ψ conformer, not the structure at global minimum. MD simulations were run to explain, in structural terms, the observed geometry of the complex. |
Author | Roldós, Virginia André, Sabine Gabius, Hans-Joachim Espinosa, Juan Félix Vauzeilles, Boris Cañada, F. Javier Jiménez-Barbero, Jesús Bleriot, Yves Fernández-Alonso, María del Carmen Vidal, Paloma Martín-Santamaría, Sonsoles |
Author_xml | – sequence: 1 givenname: Paloma surname: Vidal fullname: Vidal, Paloma organization: Discovery Chemistry Research and Technologies, Centro de Investigación Lilly, Avenida de la Industria 30, 28108 Alcobendas, Madrid (Spain) – sequence: 2 givenname: Virginia surname: Roldós fullname: Roldós, Virginia organization: Chemical and Physical Biology, CIB-CSIC, Ramiro de Maeztu 9, 28040 Madrid (Spain) – sequence: 3 givenname: María del Carmen surname: Fernández-Alonso fullname: Fernández-Alonso, María del Carmen organization: Chemical and Physical Biology, CIB-CSIC, Ramiro de Maeztu 9, 28040 Madrid (Spain) – sequence: 4 givenname: Boris surname: Vauzeilles fullname: Vauzeilles, Boris organization: CNRS and Université Paris-Sud, Glycochimie Moléculaire et Macromoléculaire, ICMMO, UMR 8182, 91405 Orsay (France) – sequence: 5 givenname: Yves surname: Bleriot fullname: Bleriot, Yves organization: Laboratoire SRSN, Université de Poitiers, 40, avenue du Recteur Pineau, 86022 Poitiers (France) – sequence: 6 givenname: F. Javier surname: Cañada fullname: Cañada, F. Javier organization: Chemical and Physical Biology, CIB-CSIC, Ramiro de Maeztu 9, 28040 Madrid (Spain) – sequence: 7 givenname: Sabine surname: André fullname: André, Sabine organization: Institut für Physiologische Chemie, Tierärztliche Fakultät, Ludwig-Maximilians-Universität München, Veterinärstr. 13, 80539 München (Germany) – sequence: 8 givenname: Hans-Joachim surname: Gabius fullname: Gabius, Hans-Joachim organization: Institut für Physiologische Chemie, Tierärztliche Fakultät, Ludwig-Maximilians-Universität München, Veterinärstr. 13, 80539 München (Germany) – sequence: 9 givenname: Jesús surname: Jiménez-Barbero fullname: Jiménez-Barbero, Jesús email: jjbarbero@cib.csic.es organization: Chemical and Physical Biology, CIB-CSIC, Ramiro de Maeztu 9, 28040 Madrid (Spain) – sequence: 10 givenname: Juan Félix surname: Espinosa fullname: Espinosa, Juan Félix email: jfespinosa@lilly.com organization: Discovery Chemistry Research and Technologies, Centro de Investigación Lilly, Avenida de la Industria 30, 28108 Alcobendas, Madrid (Spain) – sequence: 11 givenname: Sonsoles surname: Martín-Santamaría fullname: Martín-Santamaría, Sonsoles email: smsantamaria@ceu.es organization: Chemistry and Biochemistry Department, Facultad de Farmacia, Universidad CEU San Pablo, 28668-Boadilla del Monte, Madrid (Spain) |
BackLink | https://www.ncbi.nlm.nih.gov/pubmed/24105715$$D View this record in MEDLINE/PubMed https://hal.science/hal-00989845$$DView record in HAL |
BookMark | eNqFkctuEzEUhi1URNPCliXyEiQcfJsbuzaUTKUpFbTA0nI8x9R0xg7jSWB4Fh6ANQ_SZ2LSlKg7Vj46-v7P0vkP0J4PHhB6yuiUUcpfmStop5wyQRmX8gGasIQzIrI02UMTWsiMpIko9tFBjF8ppUUqxCO0zyWjScaSCfo1C96GrtW9C143-AIaMJsZO4_nzWBC61ronYmvcblq9bjUt4QnDJ_7ZsAfwIQv3v2EiOPgyc1vcjksAd_3RhwsvvlD2EtBKuevocaVNn2IgLWv8Wkf8YzcfhaHBr-Bzq3H3Boeo4dWNxGe3L2H6OPbk8tZSarz-ensqCJGskySLNHSyNxqXS_kIrWsltTmKec2s4kUYkG5TmWdbc6UW8MNZKnlgnO-0EbXQhyiF1vvlW7UsnOt7gYVtFPlUaU2u_FweZHLZM1G9vmWXXbh2wpir1oXDTSN9hBWUTEphWR5zviITreo6UKMHdidm1G1aU9t2lO79sbAszv3atFCvcP_1TUCxRb47hoY_qNTs_Lk7L6cbLMu9vBjl9XdtUozkSXq87u5KgQvzy4-Hav34i8tRLkR |
CitedBy_id | crossref_primary_10_1002_chem_201501249 crossref_primary_10_1016_j_bbagen_2014_03_016 crossref_primary_10_1039_D0OB00039F crossref_primary_10_1016_j_bmc_2021_116309 crossref_primary_10_1016_j_carres_2017_09_006 crossref_primary_10_1002_anie_201405008 crossref_primary_10_1002_ange_201405008 crossref_primary_10_1371_journal_pone_0125946 crossref_primary_10_1002_cbic_201402474 crossref_primary_10_1002_ejoc_202000813 crossref_primary_10_1016_j_carres_2018_10_011 crossref_primary_10_1021_acs_orglett_7b03741 crossref_primary_10_1021_acs_orglett_9b00862 crossref_primary_10_3389_fpls_2023_1259347 crossref_primary_10_1039_C4MD00138A crossref_primary_10_1039_D0CC03882B |
Cites_doi | 10.1039/B307802G 10.1016/0022-2364(85)90171-4 10.1039/c0ob01235a 10.1021/ja020468x 10.1093/jnen/61.7.585 10.1016/S0065-2318(01)56006-0 10.1517/14728222.2013.750651 10.1016/S0022-2836(03)00610-7 10.1021/ar000033j 10.1021/ja990601u 10.1111/j.1742-4658.2007.05851.x 10.1002/jcc.20820 10.1016/j.tibs.2011.01.005 10.1021/ja982193k 10.1002/cbic.201000705 10.1002/jcc.20035 10.1002/(SICI)1096-987X(19981115)19:14<1639::AID-JCC10>3.0.CO;2-B 10.1016/S0304-4165(01)00224-0 10.1111/febs.12001 10.1093/glycob/cwr083 10.1002/ange.19961080310 10.1021/bi051144z 10.1351/PAC-CON-11-10-01 10.1038/nsb1294-863 10.1093/glycob/9.11.1253 10.1016/j.jmb.2004.08.078 10.1139/v02-162 10.1002/psc.1338 10.1063/1.445869 10.1002/iub.358 10.1039/c0nj00277a 10.1038/cdd.2010.148 10.1039/c1an15692f 10.1063/1.465608 10.1016/j.carres.2007.04.017 10.1111/j.1365-2559.2011.03776.x 10.1007/s00418-011-0814-2 10.1002/chem.200800247 10.1021/ar300024d 10.1039/c1cc11163a 10.1039/c2ob25870f 10.1016/j.carres.2007.02.034 10.1002/(SICI)1097-458X(199703)35:3<199::AID-OMR55>3.0.CO;2-1 10.1016/j.bbagen.2011.04.001 10.3390/molecules18044026 10.1002/anie.199603031 10.1111/j.1742-4658.2010.07764.x 10.1053/j.gastro.2008.12.039 10.1016/j.bmc.2011.03.022 10.1002/1098-1136(200103)33:3<241::AID-GLIA1023>3.0.CO;2-1 10.1016/0021-9991(77)90098-5 |
ContentType | Journal Article |
Copyright | Copyright © 2013 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. Distributed under a Creative Commons Attribution 4.0 International License |
Copyright_xml | – notice: Copyright © 2013 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim – notice: Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. – notice: Distributed under a Creative Commons Attribution 4.0 International License |
DBID | BSCLL CGR CUY CVF ECM EIF NPM AAYXX CITATION 7X8 1XC |
DOI | 10.1002/chem.201301244 |
DatabaseName | Istex Medline MEDLINE MEDLINE (Ovid) MEDLINE MEDLINE PubMed CrossRef MEDLINE - Academic Hyper Article en Ligne (HAL) |
DatabaseTitle | MEDLINE Medline Complete MEDLINE with Full Text PubMed MEDLINE (Ovid) CrossRef MEDLINE - Academic |
DatabaseTitleList | MEDLINE - Academic MEDLINE CrossRef |
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: EIF name: MEDLINE url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/medline/basic-search sourceTypes: Index Database |
DeliveryMethod | fulltext_linktorsrc |
Discipline | Chemistry |
EISSN | 1521-3765 |
EndPage | 14590 |
ExternalDocumentID | oai_HAL_hal_00989845v1 10_1002_chem_201301244 24105715 CHEM201301244 ark_67375_WNG_932HMSVB_Q |
Genre | article Research Support, Non-U.S. Gov't Journal Article |
GrantInformation_xml | – fundername: European Commission funderid: BM1003; CM1102 – fundername: Spanish MINECO funderid: CTQ2009‐08536; CTQ2012‐32025; CTQ2011‐22724 – fundername: Fundación Universitaria San Pablo CEU funderid: USP‐PC 14/2011 and 13/2012 – fundername: Comunidad de Madrid – fundername: GlycoHIT program funderid: 260600 – fundername: GLYCOPHARM ITN‐project |
GroupedDBID | --- -DZ -~X .3N .GA .Y3 05W 0R~ 10A 1L6 1OB 1OC 1ZS 29B 33P 3SF 3WU 4.4 4ZD 50Y 50Z 51W 51X 52M 52N 52O 52P 52S 52T 52U 52W 52X 53G 5GY 5VS 66C 6J9 702 77Q 7PT 8-0 8-1 8-3 8-4 8-5 8UM 930 A03 AAESR AAEVG AAHHS AAJUZ AANLZ AAONW AASGY AAXRX AAZKR ABCQN ABCUV ABCVL ABDBF ABHUG ABIJN ABJNI ABLJU ABPVW ACAHQ ACBWZ ACCFJ ACCZN ACGFS ACIWK ACNCT ACPOU ACXBN ACXME ACXQS ADAWD ADBBV ADDAD ADEOM ADIZJ ADKYN ADMGS ADOZA ADXAS ADZMN ADZOD AEEZP AEGXH AEIGN AEIMD AEQDE AEUQT AEUYR AFBPY AFFPM AFGKR AFPWT AFRAH AFVGU AFZJQ AGJLS AHBTC AHMBA AIURR AIWBW AJBDE AJXKR ALAGY ALMA_UNASSIGNED_HOLDINGS ALUQN AMBMR AMYDB ASPBG ATUGU AUFTA AVWKF AZBYB AZFZN AZVAB BAFTC BDRZF BFHJK BHBCM BMNLL BMXJE BNHUX BROTX BRXPI BSCLL BY8 CS3 D-E D-F DCZOG DPXWK DR2 DRFUL DRSTM EBD EBS EJD F00 F01 F04 F5P G-S G.N GNP GODZA H.T H.X HBH HHY HHZ HZ~ IX1 J0M JPC KQQ LATKE LAW LC2 LC3 LEEKS LH4 LITHE LOXES LP6 LP7 LUTES LW6 LYRES MEWTI MK4 MRFUL MRSTM MSFUL MSSTM MXFUL MXSTM N04 N05 N9A NF~ NNB O66 O9- P2W P2X P4D PQQKQ Q.N Q11 QB0 QRW R.K RGC RNS ROL RWI RX1 RYL SUPJJ TN5 TWZ UB1 UPT V2E V8K W8V W99 WBFHL WBKPD WH7 WIB WIH WIK WJL WOHZO WQJ WRC WXSBR WYISQ XG1 XPP XV2 YZZ ZZTAW ~IA ~WT AITYG HGLYW OIG CGR CUY CVF ECM EIF NPM AAYXX CITATION 7X8 1XC |
ID | FETCH-LOGICAL-c4174-75a4c48faadb4b6f1d40f8622f7f5433b02a64d720138fc2ce76f23222bacad33 |
IEDL.DBID | DR2 |
ISSN | 0947-6539 |
IngestDate | Tue Oct 15 15:56:40 EDT 2024 Fri Aug 16 06:15:25 EDT 2024 Fri Aug 23 02:36:54 EDT 2024 Sat Sep 28 07:52:29 EDT 2024 Sat Aug 24 01:03:15 EDT 2024 Wed Jan 17 05:06:20 EST 2024 |
IsPeerReviewed | true |
IsScholarly | true |
Issue | 43 |
Keywords | conformation analysis structure-activity relationships NMR spectroscopy molecular modeling glycoconjugates |
Language | English |
License | Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. Distributed under a Creative Commons Attribution 4.0 International License: http://creativecommons.org/licenses/by/4.0 |
LinkModel | DirectLink |
MergedId | FETCHMERGED-LOGICAL-c4174-75a4c48faadb4b6f1d40f8622f7f5433b02a64d720138fc2ce76f23222bacad33 |
Notes | ArticleID:CHEM201301244 istex:970687E1309154A53A01E1102849AE24B860C502 European Commission - No. BM1003; No. CM1102 Comunidad de Madrid GLYCOPHARM ITN-project Fundación Universitaria San Pablo CEU - No. USP-PC 14/2011 and 13/2012 ark:/67375/WNG-932HMSVB-Q Spanish MINECO - No. CTQ2009-08536; No. CTQ2012-32025; No. CTQ2011-22724 GlycoHIT program - No. 260600 ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
PMID | 24105715 |
PQID | 1443418812 |
PQPubID | 23479 |
PageCount | 10 |
ParticipantIDs | hal_primary_oai_HAL_hal_00989845v1 proquest_miscellaneous_1443418812 crossref_primary_10_1002_chem_201301244 pubmed_primary_24105715 wiley_primary_10_1002_chem_201301244_CHEM201301244 istex_primary_ark_67375_WNG_932HMSVB_Q |
PublicationCentury | 2000 |
PublicationDate | 2013-10-18 October 18, 2013 2013-Oct-18 20131018 |
PublicationDateYYYYMMDD | 2013-10-18 |
PublicationDate_xml | – month: 10 year: 2013 text: 2013-10-18 day: 18 |
PublicationDecade | 2010 |
PublicationPlace | Weinheim |
PublicationPlace_xml | – name: Weinheim – name: Germany |
PublicationTitle | Chemistry : a European journal |
PublicationTitleAlternate | Chem. Eur. J |
PublicationYear | 2013 |
Publisher | WILEY-VCH Verlag WILEY‐VCH Verlag Wiley-VCH Verlag |
Publisher_xml | – name: WILEY-VCH Verlag – name: WILEY‐VCH Verlag – name: Wiley-VCH Verlag |
References | S. André, B. Liu, H.-J. Gabius, R. Roy, Org. Biomol. Chem. 2003, 1, 3909-3916 ROESY: A. Bax, D. G. Davis, J. Magn. Reson. 1985, 63, 207-213. J. L. Asensio, A. Ardá, F. J. Cañada, J. Jiménez-Barbero, Acc. Chem. Res. 2013, 46, 946-954. P. A. Kollman, I. Massova, C. Reyes, B. Kuhn, S. H. Huo, L. Chong, M. Lee, T. Lee, Y. Duan, W. Wang, O. Donini, P. Cieplak, J. Srinivasan, D. A. Case, T. E. Cheatham, Acc. Chem. Res. 2000, 33, 889-897. S. Saussez, L. de Leval, C. Decaestecker, N. Sirtaine, S. Cludts, A. Duray, D. Chevalier, S. André, H.-J. Gabius, M. Remmelink, X. Leroy, Histol. Histopathol. 2010, 25, 541-550 J. L. Asensio, J. F. Espinosa, H. Dietrich, F. J. Cañada, R. R. Schmidt, M. Martín-Lomas, S. André, H.-J. Gabius, J. Jiménez-Barbero, J. Am. Chem. Soc. 1999, 121, 8995-9000 S. Saussez, D. Decaestecker, F. Lorfevre, D. R. Cucu, G. Mortuaire, D. Chevalier, A. Wacreniez, H. Kaltner, S. André, G. Toubeau, I. Camby, H.-J. Gabius, R. Kiss, Int. J. Oncol. 2007, 30, 1109-1117 J.-M. Beau, B. Vauzeilles, T. Skrydstrup, C-Glycosyl Analogs of Oligosaccharides and Glycosyl Amino Acids in Glycoscience, Vol. 3 (Eds.: B. O. Fraser-Reid, K. Tatsuta, J. Thiem), Springer, Berlin, 2001, pp. 2679-2724. J. Jiménez-Barbero, J. F. Espinosa, J. L. Asensio, F. J. Cañada, A. Poveda, Adv. Carbohydr. Chem. Biochem. 2000, 56, 235-284. H. Sanchez-Ruderisch, K. M. Detjen, M. Welzel, S. André, C. Fischer, H.-J. Gabius, S. Rosewicz, Cell Death Differ. 2011, 18, 806-816 M. Amano, H. Eriksson, J. C. Manning, K. M. Detjen, S. André, S.-I. Nishimura, J. Lehtiö, H.-J. Gabius, FEBS J. 2012, 279, 4062-4080. M. C. Miller, J. P. Ribeiro, V. Roldós, S. Martín-Santamaría, F. J. Cañada, I. A. Nesmelova, S. André, M. Pang, A. A. Klyosov, L. G. Baum, J. Jiménez-Barbero, H.-J. Gabius, K. H. Mayo, Glycobiology 2011, 21, 1627-1641. J.-P. Ryckaert, G. Ciccotti, H. J. C. Berendsen, J. Comput. Phys. 1977, 23, 327-341. M. Remmelink, L. de Leval, C. Decaestecker, A. Duray, E. Crompot, N. Sirtaine, S. André, H. Kaltner, X. Leroy, H.-J. Gabius, S. Saussez, Histopathology 2011, 58, 543-556. S. André, H. Sanchez-Ruderisch, H. Nakagawa, M. Buchholz, J. Kopitz, P. Forberich, W. Kemmner, C. Böck, K. Deguchi, K. M. Detjen, B. Wiedenmann, M. von Knebel Doeberitz, T. M. Gress, S.-I. Nishimura, S. Rosewicz, H.-J. Gabius, FEBS J. 2007, 274, 3233-3256 S. Vandenbussche, D. Díaz, M. C. Fernández-Alonso, W. Pan, S. P. Vincent, G. Cuevas, F. J. Cañada, J. Jiménez-Barbero, K. Bartik, Chem. Eur. J. 2008, 14, 7570-7578 A. Göhler, C. Büchner, S. André, S. Doose, H. Kaltner, H.-J. Gabius, Analyst 2011, 136, 5270-5276 O. Roda, E. Ortíz-Zapater, N. Martínez-Bosch, R. Gutiérrez-Gallego, M. Vila-Perelló, C. Ampurdanés, H.-J. Gabius, S. André, D. Andreu, F. X. Real, P. Navarro, Gastroenterology 2009, 136, 1379-1390 S. André, P. J. Cejas Ortega, M. A. Perez, R. Roy, H.-J. Gabius, Glycobiology 1999, 9, 1253-1261 K. Smetana, Jr., S. André, H. Kaltner, J. Kopitz, H.-J. Gabius, Exp. Opin. Ther. Targ. 2013, 17, 379-392. Y. Bourne, B. Bolgiano, D. I. Liao, G. Strecker, P. Cantau, O. Herzberg, T. Feizi, C. Cambillau, Nat. Struct. Biol. 1994, 1, 863-870. T. K. Dam, H.-J. Gabius, S. André, H. Kaltner, M. Lensch, C. F. Brewer, Biochemistry 2005, 44, 12564-12571. Angew. Chem. Int. Ed. Engl. 1996, 35, 303-306 S. André, O. Renaudet, I. Bossu, P. Dumy, H.-J. Gabius, J. Pept. Sci. 2011, 17, 427-437 G. M. Morris, D. S. Goodsell, R. S. Halliday, R. Huey, W. E. Hart, R. K. Belew, A. J. Olson, J. Comput. Chem. 1998, 19, 1639-1662. H. Sanchez-Ruderisch, C. Fischer, K. M. Detjen, M. Welzel, A. Wimmel, J. C. Manning, S. André, H.-J. Gabius, FEBS J. 2010, 277, 3552-3563 S. André, D. Giguère, T. K. Dam, F. Brewer, H.-J. Gabius, R. Roy, New J. Chem. 2010, 34, 2229-2240 S. André, C. Grandjean, F. M. Gautier, S. Bernardi, F. Sansone, H.-J. Gabius, R. Ungaro, Chem. Commun. 2011, 47, 6126-6128 S. Martín-Santamaría, H.-J. Gabius, J. Jiménez-Barbero, Pure Appl. Chem. 2012, 84, 49-64. M. F. López-Lucendo, D. Solís, S. André, J. Hirabayashi, K.-I. Kasai, H. Kaltner, H.-J. Gabius, A. Romero, J. Mol. Biol. 2004, 343, 957-970. J. Kopitz, M. Bergmann, H.-J. Gabius, IUBMB Life 2010, 62, 624-628 G.-N. Wang, S. André, H.-J. Gabius, P. V. Murphy, Org. Biomol. Chem. 2012, 10, 6893-6907 S. Rorive, N. Belot, C. Decaestecker, F. Lefranc, L. Gordower, S. Micik, C. A. Maurage, H. Kaltner, M.-M. Ruchoux, A. Danguy, H.-J. Gabius, I. Salmon, R. Kiss, I. Camby, GLIA 2001, 33, 241-255 H. Kaltner, H.-J. Gabius, Histol. Histopathol. 2012, 27, 397-416 J. Iwaki, H. Tateno, N. Nishi, T. Minamisawa, S. Nakamura-Tsuruta, Y. Itakura, J. Kominami, T. Urashima, T. Nakamura, J. Hirabayashi, Biochim. Biophys. Acta Gen. Subj. 2011, 1810, 643-651. P. Vidal, B. Vauzeilles, Y. Bleriot, M. Sollogoub, P. Sinaÿ, J. Jiménez-Barbero, J. F. Espinosa, Carbohydr. Res. 2007, 342, 1910-1917. D. Giguère, S. André, M. A. Bonin, M. A. Bellefleur, A. Provencal, P. Cloutier, B. Pucci, R. Roy, H.-J. Gabius, Bioorg. Med. Chem. 2011, 19, 3280-3287 I. Camby, N. Belot, F. Lefranc, N. Sadeghi, Y. de Launoit, H. Kaltner, S. Murette, F. Darro, A. Danguy, I. Salmon, H.-J. Gabius, R. Kiss, J. Neuropathol. Exp. Neurol. 2002, 61, 585-596 HSQC-NOESY: R. Wagner, S. Berger, Magn. Reson. Chem. 1996, 35, 199-202. H. Gohlke, C. Kiel, D. A. Case, J. Mol. Biol. 2003, 330, 891-913. N. Ahmad, H.-J. Gabius, H. Kaltner, S. André, I. Kuwabara, F.-T. Liu, S. Oscarson, T. Norberg, C. F. Brewer, Can. J. Chem. 2002, 80, 1096-1104 F. A. Habermann, S. André, H. Kaltner, D. Kübler, F. Sinowatz, H.-J. Gabius, Histochem. Cell Biol. 2011, 135, 539-552. D. M. York, T. A. Darden and L. G. Pedersen, J. Chem. Phy. 1993, 99, 8345-8348. V. García-Aparicio, M. Sollogoub, Y. Blériot, V. Colliou, S. André, J. L. Asensio, F. J. Cañada, H.-J. Gabius, P. Sinaÿ, J. Jiménez-Barbero, Carbohydr. Res. 2007, 342, 1918-1928 S. Martín-Santamaría, S. André, E. Buzamet, R. Caraballo, G. Fernández-Cureses, M. Morando, J. P. Ribeiro, K. Ramírez-Gualito, B. de Pascual-Teresa, F. J. Cañada, M. Menéndez, O. Ramström, J. Jiménez-Barbero, D. Solís, H.-J. Gabius, Org. Biomol. Chem. 2011, 9, 5445-5455. V. Roldós, F. J. Cañada, J. Jiménez-Barbero, ChemBioChem 2011, 12, 990-1005. K. N. Kirschner, A. B. Yongye, S. M. Tschampel, J. Gonzalez-Outeirino, C. R. Daniels, B. L. Foley, R. J. Woods, J. Comput. Chem. 2008, 29, 622-655. W. L. Jorgensen, J. Chandrasekhar, J. D. Madura, R. W. Impey, M. L. Klein, J. Chem. Phys. 1983, 79, 926-935. J. M. Alonso-Plaza, M. A. Canales, M. Jiménez, J. L. Roldán, A. García-Herrero, L. Iturrino, J. L. Asensio, F. J. Cañada, A. Romero, H.-C. Siebert, S. André, D. Solís, H.-J. Gabius, J. Jiménez-Barbero, Biochim. Biophys. Acta Gen. Subj. 2001, 1568, 225-236. J. F. Espinosa, F. J. Cañada, J. L. Asensio, H. Dietrich, M. Martín-Lomas, R. R. Schmidt, J. Jiménez-Barbero, Angew. Chem. 1996, 108, 323-326 R. Ravishankar, A. Surolia, M. Vijayan, S. Lim, Y. Kishi, J. Am. Chem. Soc. 1998, 120, 11297-11303 H.-J. Gabius, S. André, J. Jiménez-Barbero, A. Romero, D. Solís, Trends Biochem. Sci. 2011, 36, 298-313 J. Wang, R. M. Wolf, J. W. Caldwell, P. A. Kollman, D. A. Case, J. Comput. Chem. 2004, 25, 1157-1174. L. M. Mikkelsen, M. J. Hernaiz, M. Martín-Pastor, T. Skrydstrup, J. Jiménez-Barbero, J. Am. Chem. Soc. 2002, 124, 14940-14951. P. V. Murphy, S. André, H.-J. Gabius, Molecules 2013, 18, 4026-4053. 2004; 25 2007; 342 1999; 121 2011; 12 1985; 63 2007; 30 2011; 58 1977; 23 2011; 17 1996; 35 2011; 19 2011; 18 2012; 10 2010; 62 2013; 18 1998; 19 2013; 17 2010; 25 2001 2000; 56 2008; 29 2010; 277 2011; 21 2012; 27 2003; 1 1998; 120 2004; 343 2010; 34 2011; 136 2011; 135 2013; 46 2008; 14 2001; 1568 2011; 36 2002; 80 2005; 44 2009; 136 1983; 79 2003; 330 2011; 9 1999; 9 2002; 61 2002; 124 1993; 99 2000; 33 1996 1996; 108 35 2007; 274 2011; 1810 2011; 47 2012; 279 1994; 1 2001; 33 2012; 84 e_1_2_6_51_2 e_1_2_6_53_2 e_1_2_6_30_2 Saussez S. (e_1_2_6_47_2) 2010; 25 e_1_2_6_19_2 Beau J.‐M. (e_1_2_6_1_2) 2001 e_1_2_6_34_2 e_1_2_6_59_2 e_1_2_6_11_2 e_1_2_6_32_2 e_1_2_6_17_2 e_1_2_6_38_2 e_1_2_6_55_2 e_1_2_6_15_2 e_1_2_6_36_2 e_1_2_6_57_2 e_1_2_6_62_2 e_1_2_6_64_2 e_1_2_6_20_2 e_1_2_6_41_2 e_1_2_6_60_2 e_1_2_6_7_2 e_1_2_6_9_2 e_1_2_6_3_2 e_1_2_6_5_2 e_1_2_6_24_2 e_1_2_6_22_2 e_1_2_6_49_2 e_1_2_6_28_2 e_1_2_6_43_2 e_1_2_6_66_2 e_1_2_6_26_2 e_1_2_6_50_2 e_1_2_6_52_2 e_1_2_6_31_2 e_1_2_6_18_2 e_1_2_6_12_2 e_1_2_6_35_2 e_1_2_6_58_2 e_1_2_6_10_2 e_1_2_6_33_2 e_1_2_6_16_2 e_1_2_6_39_2 e_1_2_6_54_2 e_1_2_6_14_2 e_1_2_6_37_2 e_1_2_6_56_2 e_1_2_6_61_2 e_1_2_6_63_2 e_1_2_6_42_2 e_1_2_6_40_2 e_1_2_6_8_2 Kaltner H. (e_1_2_6_13_2) 2012; 27 e_1_2_6_29_2 e_1_2_6_4_2 e_1_2_6_6_2 e_1_2_6_4_3 e_1_2_6_23_2 Saussez S. (e_1_2_6_45_2) 2007; 30 e_1_2_6_48_2 e_1_2_6_2_2 e_1_2_6_21_2 e_1_2_6_65_2 e_1_2_6_27_2 e_1_2_6_44_2 e_1_2_6_25_2 e_1_2_6_46_2 |
References_xml | – volume: 18 start-page: 806 year: 2011 end-page: 816 publication-title: Cell Death Differ. – volume: 21 start-page: 1627 year: 2011 end-page: 1641 publication-title: Glycobiology – volume: 1 start-page: 3909 year: 2003 end-page: 3916 publication-title: Org. Biomol. Chem. – volume: 14 start-page: 7570 year: 2008 end-page: 7578 publication-title: Chem. Eur. J. – volume: 136 start-page: 5270 year: 2011 end-page: 5276 publication-title: Analyst – volume: 17 start-page: 427 year: 2011 end-page: 437 publication-title: J. Pept. Sci. – volume: 61 start-page: 585 year: 2002 end-page: 596 publication-title: J. Neuropathol. Exp. Neurol. – volume: 135 start-page: 539 year: 2011 end-page: 552 publication-title: Histochem. Cell Biol. – volume: 44 start-page: 12564 year: 2005 end-page: 12571 publication-title: Biochemistry – volume: 12 start-page: 990 year: 2011 end-page: 1005 publication-title: ChemBioChem – volume: 18 start-page: 4026 year: 2013 end-page: 4053 publication-title: Molecules – volume: 25 start-page: 541 year: 2010 end-page: 550 publication-title: Histol. Histopathol. – volume: 330 start-page: 891 year: 2003 end-page: 913 publication-title: J. Mol. Biol. – volume: 136 start-page: 1379 year: 2009 end-page: 1390 publication-title: Gastroenterology – volume: 58 start-page: 543 year: 2011 end-page: 556 publication-title: Histopathology – volume: 25 start-page: 1157 year: 2004 end-page: 1174 publication-title: J. Comput. Chem. – volume: 30 start-page: 1109 year: 2007 end-page: 1117 publication-title: Int. J. Oncol. – volume: 33 start-page: 889 year: 2000 end-page: 897 publication-title: Acc. Chem. Res. – volume: 19 start-page: 3280 year: 2011 end-page: 3287 publication-title: Bioorg. Med. Chem. – volume: 120 start-page: 11297 year: 1998 end-page: 11303 publication-title: J. Am. Chem. Soc. – volume: 19 start-page: 1639 year: 1998 end-page: 1662 publication-title: J. Comput. Chem. – volume: 34 start-page: 2229 year: 2010 end-page: 2240 publication-title: New J. Chem. – volume: 47 start-page: 6126 year: 2011 end-page: 6128 publication-title: Chem. Commun. – volume: 63 start-page: 207 year: 1985 end-page: 213 publication-title: J. Magn. Reson. – volume: 80 start-page: 1096 year: 2002 end-page: 1104 publication-title: Can. J. Chem. – volume: 342 start-page: 1910 year: 2007 end-page: 1917 publication-title: Carbohydr. Res. – volume: 121 start-page: 8995 year: 1999 end-page: 9000 publication-title: J. Am. Chem. Soc. – volume: 46 start-page: 946 year: 2013 end-page: 954 publication-title: Acc. Chem. Res. – volume: 1810 start-page: 643 year: 2011 end-page: 651 publication-title: Biochim. Biophys. Acta Gen. Subj. – volume: 23 start-page: 327 year: 1977 end-page: 341 publication-title: J. Comput. Phys. – volume: 36 start-page: 298 year: 2011 end-page: 313 publication-title: Trends Biochem. Sci. – volume: 124 start-page: 14940 year: 2002 end-page: 14951 publication-title: J. Am. Chem. Soc. – volume: 342 start-page: 1918 year: 2007 end-page: 1928 publication-title: Carbohydr. Res. – volume: 1 start-page: 863 year: 1994 end-page: 870 publication-title: Nat. Struct. Biol. – volume: 33 start-page: 241 year: 2001 end-page: 255 publication-title: GLIA – volume: 17 start-page: 379 year: 2013 end-page: 392 publication-title: Exp. Opin. Ther. Targ. – volume: 279 start-page: 4062 year: 2012 end-page: 4080 publication-title: FEBS J. – start-page: 2679 year: 2001 end-page: 2724 – volume: 62 start-page: 624 year: 2010 end-page: 628 publication-title: IUBMB Life – volume: 343 start-page: 957 year: 2004 end-page: 970 publication-title: J. Mol. Biol. – volume: 35 start-page: 199 year: 1996 end-page: 202 publication-title: Magn. Reson. Chem. – volume: 274 start-page: 3233 year: 2007 end-page: 3256 publication-title: FEBS J. – volume: 84 start-page: 49 year: 2012 end-page: 64 publication-title: Pure Appl. Chem. – volume: 27 start-page: 397 year: 2012 end-page: 416 publication-title: Histol. Histopathol. – volume: 56 start-page: 235 year: 2000 end-page: 284 publication-title: Adv. Carbohydr. Chem. Biochem. – volume: 108 35 start-page: 323 303 year: 1996 1996 end-page: 326 306 publication-title: Angew. Chem. Angew. Chem. Int. Ed. Engl. – volume: 10 start-page: 6893 year: 2012 end-page: 6907 publication-title: Org. Biomol. Chem. – volume: 9 start-page: 1253 year: 1999 end-page: 1261 publication-title: Glycobiology – volume: 1568 start-page: 225 year: 2001 end-page: 236 publication-title: Biochim. Biophys. Acta Gen. Subj. – volume: 29 start-page: 622 year: 2008 end-page: 655 publication-title: J. Comput. Chem. – volume: 9 start-page: 5445 year: 2011 end-page: 5455 publication-title: Org. Biomol. Chem. – volume: 277 start-page: 3552 year: 2010 end-page: 3563 publication-title: FEBS J. – volume: 79 start-page: 926 year: 1983 end-page: 935 publication-title: J. Chem. Phys. – volume: 99 start-page: 8345 year: 1993 end-page: 8348 publication-title: J. Chem. Phy. – ident: e_1_2_6_51_2 doi: 10.1039/B307802G – ident: e_1_2_6_65_2 doi: 10.1016/0022-2364(85)90171-4 – ident: e_1_2_6_66_2 – ident: e_1_2_6_40_2 doi: 10.1039/c0ob01235a – ident: e_1_2_6_49_2 – ident: e_1_2_6_3_2 – volume: 25 start-page: 541 year: 2010 ident: e_1_2_6_47_2 publication-title: Histol. Histopathol. contributor: fullname: Saussez S. – ident: e_1_2_6_6_2 doi: 10.1021/ja020468x – ident: e_1_2_6_44_2 doi: 10.1093/jnen/61.7.585 – ident: e_1_2_6_2_2 doi: 10.1016/S0065-2318(01)56006-0 – ident: e_1_2_6_14_2 doi: 10.1517/14728222.2013.750651 – ident: e_1_2_6_37_2 doi: 10.1016/S0022-2836(03)00610-7 – ident: e_1_2_6_57_2 – ident: e_1_2_6_36_2 doi: 10.1021/ar000033j – ident: e_1_2_6_8_2 doi: 10.1021/ja990601u – ident: e_1_2_6_16_2 doi: 10.1111/j.1742-4658.2007.05851.x – ident: e_1_2_6_35_2 doi: 10.1002/jcc.20820 – ident: e_1_2_6_12_2 doi: 10.1016/j.tibs.2011.01.005 – ident: e_1_2_6_5_2 doi: 10.1021/ja982193k – ident: e_1_2_6_27_2 doi: 10.1002/cbic.201000705 – start-page: 2679 volume-title: C‐Glycosyl Analogs of Oligosaccharides and Glycosyl Amino Acids in Glycoscience, Vol. 3 year: 2001 ident: e_1_2_6_1_2 contributor: fullname: Beau J.‐M. – ident: e_1_2_6_34_2 doi: 10.1002/jcc.20035 – ident: e_1_2_6_11_2 – ident: e_1_2_6_28_2 doi: 10.1002/(SICI)1096-987X(19981115)19:14<1639::AID-JCC10>3.0.CO;2-B – ident: e_1_2_6_22_2 – ident: e_1_2_6_39_2 doi: 10.1016/S0304-4165(01)00224-0 – ident: e_1_2_6_20_2 doi: 10.1111/febs.12001 – ident: e_1_2_6_21_2 doi: 10.1093/glycob/cwr083 – ident: e_1_2_6_4_2 doi: 10.1002/ange.19961080310 – ident: e_1_2_6_24_2 doi: 10.1021/bi051144z – ident: e_1_2_6_30_2 – ident: e_1_2_6_60_2 – ident: e_1_2_6_10_2 doi: 10.1351/PAC-CON-11-10-01 – ident: e_1_2_6_38_2 doi: 10.1038/nsb1294-863 – ident: e_1_2_6_50_2 doi: 10.1093/glycob/9.11.1253 – ident: e_1_2_6_29_2 doi: 10.1016/j.jmb.2004.08.078 – ident: e_1_2_6_23_2 doi: 10.1139/v02-162 – ident: e_1_2_6_52_2 doi: 10.1002/psc.1338 – ident: e_1_2_6_61_2 doi: 10.1063/1.445869 – ident: e_1_2_6_17_2 doi: 10.1002/iub.358 – ident: e_1_2_6_58_2 doi: 10.1039/c0nj00277a – ident: e_1_2_6_15_2 – ident: e_1_2_6_19_2 doi: 10.1038/cdd.2010.148 – ident: e_1_2_6_32_2 doi: 10.1039/c1an15692f – ident: e_1_2_6_63_2 doi: 10.1063/1.465608 – ident: e_1_2_6_25_2 doi: 10.1016/j.carres.2007.04.017 – volume: 30 start-page: 1109 year: 2007 ident: e_1_2_6_45_2 publication-title: Int. J. Oncol. contributor: fullname: Saussez S. – ident: e_1_2_6_48_2 doi: 10.1111/j.1365-2559.2011.03776.x – ident: e_1_2_6_59_2 doi: 10.1007/s00418-011-0814-2 – ident: e_1_2_6_26_2 – ident: e_1_2_6_31_2 doi: 10.1002/chem.200800247 – ident: e_1_2_6_33_2 doi: 10.1021/ar300024d – volume: 27 start-page: 397 year: 2012 ident: e_1_2_6_13_2 publication-title: Histol. Histopathol. contributor: fullname: Kaltner H. – ident: e_1_2_6_53_2 doi: 10.1039/c1cc11163a – ident: e_1_2_6_42_2 – ident: e_1_2_6_55_2 doi: 10.1039/c2ob25870f – ident: e_1_2_6_9_2 doi: 10.1016/j.carres.2007.02.034 – ident: e_1_2_6_64_2 doi: 10.1002/(SICI)1097-458X(199703)35:3<199::AID-OMR55>3.0.CO;2-1 – ident: e_1_2_6_41_2 doi: 10.1016/j.bbagen.2011.04.001 – ident: e_1_2_6_56_2 doi: 10.3390/molecules18044026 – ident: e_1_2_6_4_3 doi: 10.1002/anie.199603031 – ident: e_1_2_6_7_2 – ident: e_1_2_6_18_2 doi: 10.1111/j.1742-4658.2010.07764.x – ident: e_1_2_6_46_2 doi: 10.1053/j.gastro.2008.12.039 – ident: e_1_2_6_54_2 doi: 10.1016/j.bmc.2011.03.022 – ident: e_1_2_6_43_2 doi: 10.1002/1098-1136(200103)33:3<241::AID-GLIA1023>3.0.CO;2-1 – ident: e_1_2_6_62_2 doi: 10.1016/0021-9991(77)90098-5 |
SSID | ssj0009633 |
Score | 2.2454724 |
Snippet | The human lectin galectin‐1 (hGal‐1) translates sugar signals, that is, β‐galactosides, into effects on the level of cells, for example, growth regulation, and... The human lectin galectin-1 (hGal-1) translates sugar signals, that is, β-galactosides, into effects on the level of cells, for example, growth regulation, and... Abstract The human lectin galectin‐1 (hGal‐1) translates sugar signals, that is, β‐galactosides, into effects on the level of cells, for example, growth... The human lectin galectin-1 (hGal-1) translates sugar signals, that is, beta-galactosides, into effects on the level of cells, for example, growth regulation,... |
SourceID | hal proquest crossref pubmed wiley istex |
SourceType | Open Access Repository Aggregation Database Index Database Publisher |
StartPage | 14581 |
SubjectTerms | Catalysis Chemical Sciences conformation analysis Galectin 1 - chemistry Galectin 1 - metabolism glycoconjugates Glycomics Glycosides - chemistry Humans Hydrogen Bonding Lactose - chemistry Molecular Conformation Molecular Dynamics Simulation molecular modeling NMR spectroscopy Organic chemistry Other structure-activity relationships Substrate Specificity |
Title | Conformational Selection in Glycomimetics: Human Galectin-1 Only Recognizes syn-Ψ-Type Conformations of β-1,3-Linked Lactose and Its C-Glycosyl Derivative |
URI | https://api.istex.fr/ark:/67375/WNG-932HMSVB-Q/fulltext.pdf https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fchem.201301244 https://www.ncbi.nlm.nih.gov/pubmed/24105715 https://search.proquest.com/docview/1443418812 https://hal.science/hal-00989845 |
Volume | 19 |
hasFullText | 1 |
inHoldings | 1 |
isFullTextHit | |
isPrint | |
link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwpV3NbtQwELagHODC_0_4k0EILqSNHTteuJWF7oLaIloKvVnjJBZVlyxqdiu2Jx6Bx-iZB-lD8CTMOE3aRUhIcIkcx05iZ-z5HM98w9gjgzA51-SxjMo9Vrl2scs0xAakyFxiIBfkKLy2ng231JttvX3Ki7_hh-h-uNHICPM1DXBw9dIJaSi2iTzJcQ4mFYWTMLHpESraOOGPQulqYskrExMHa8vamMil-epzWunsJ7KJPEfd_PVPwHMexwZFtHKJQduExv5kd3E6cYv5wW_sjv_Txsvs4jFK5cuNWF1hZ8rqKjvfb4PDXWOH5CnY-j1iyc0QTgfTfKfig9EMH7Tzmfwj6-c87BPwAYQS1c9v3wV_W41mfKOxXTooa17PKP_oEA-0MOan717zsedHP6je0xSPtHouC75KgYLqkkNV8NeTmvfxUnhwPRvxlziu9gOl-XW2tfLqfX8YHwd9iHMlyDZUg8pVzwMUTrnMi0IlHpdd0huvVZq6REKmCkO90vO5zEuTeUn7RQ5yKNL0BluoxlV5i_FUuCwptElwwlfOg5OQAGTGey9AgInYk_aj2y8Nt4dtWJylpZ63Xc9H7CHKRFeIKLmHy6uW8oiQ9VlP6X0RscdBZLpisLdLZnNG24_rA4tAebi2-eGFfRexB61MWfxstEMDVTme1rgOU4gqegi6InazEbbubpIMco3QEZNBZP7yypYoNbqz2_9S6Q67QGnS1KJ3ly1M9qblPYRgE3c_DLNfZUIuoA |
link.rule.ids | 230,315,786,790,891,1382,27955,27956,46327,46751 |
linkProvider | Wiley-Blackwell |
linkToHtml | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwpV3NbtQwELZoeygX_n_Cr0EILqSNHTteuJUt3RR2F9Ef4GbZSSyqLlnU7FZsTzwCj9EzD9KH4EmYcZqURUhIcLESx3Zie8Yzjme-IeSRAjU5k-ixDMI9FJm0oU2kCZXhLLGRMhlDR-HBMEl3xasPsrEmRF-YGh-i_eGGnOHXa2Rw_CG9eoYaCp1CV3JYhFFGLZAl4HmJvLm-dYYgBfRVR5MXKkQU1ga3MeKr8_Xn5NLCR7SKXMKB_vIn1XNek_WiaOMisU0naguU_ZXpxK5kR7_hO_5XLy-RC6eKKl2rKesyOVeUV8hyt4kPd5Uco7Ng4_oIJbd9RB24pnsl7Y1m8Ka9T-giWT2n_qiA9owvUf74-o3RN-VoRrdq86WjoqLVDPNPjiHBvTH9tfWKjh09-Y71nsaQ4ga6yGkfYwVVBTVlTjcnFe3CI__iajai68Bahx7V_BrZ3Xi5003D07gPYSYYmodKIzLRccbkVtjEsVxEDnZe3CknRRzbiJtE5ApHpeMynhUqcRyPjKzJTB7H18liOS6Lm4TGzCZRLlUEa76wzlhuImMS5ZxjhhkVkCfNrOvPNbyHroGcucaR1-3IB-QhEEVbCFG507W-xjzEZH3WEfKQBeSxp5m2mDnYR8s5JfX7YU-DrpwOtt-90G8D8qAhKg3Thoc0pizG0wq2YgIUiw7oXQG5UVNb2xpHm1zFZEC4p5m_fLJGVI327ta_VLpPltOdQV_3N4evb5PzmI-Cm3XukMXJwbS4CxrZxN7zPPcTMq4ywA |
linkToPdf | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwpV3NbtQwELZoK0Ev_FPCr0EILk0bO3YcuJVddrewXaCl0JtlJ7GoumSrZrdie-IReIyeeZA-BE_CTNKkXYSEBJcocfwT22PPTDzzDSFPFIjJiUSPZWDuvkik9W0kja8MZ5ENlEkYOgpvDKLetni9I3fOefFX-BDNDzdcGeV-jQt8P3WrZ6Ch0Cf0JIc9GFnUHFkQUchR_WpvngFIAXlVweSF8hGEtYZtDPjqbPkZtjT3GY0iF3Ccv_5J8pwVZEtO1LlCTN2HygBlb2UytivJ0W_wjv_Tyavk8qmYStcqurpGLmT5dXKpVUeHu0GO0VWwdnyEnFtlPB24p7s57Q6n0NDuF3SQLF7Q8qCAdk2ZI__57Tujb_PhlG5WxktHWUGLKaafHMMFNWN6vvaCjhw9-YHllkO4ovqcpbSPkYKKjJo8pevjgrbgVdlwMR3SNiyswxLT_CbZ7rz60Or5p1Ef_EQwNA6VRiQidsakVtjIsVQEDvQu7pSTIgxtwE0kUoWjEruEJ5mKHMcDI2sSk4bhLTKfj_LsNqEhs1GQShXAji-sM5abwJhIOeeYYUZ55Fk96Xq_AvfQFYwz1zjyuhl5jzwGmmgyISZ3b62vMQ0RWZ_HQh4yjzwtSabJZg720G5OSf1p0NUgKfc2tj6-1O898qimKQ3Thkc0Js9GkwIUMQFiRQxSl0eWKmJrauNokauY9AgvSeYvn6wRU6N5uvMvhR6Si-_aHd1fH7y5SxYxGbk2i--R-fHBJLsP4tjYPihX3C-AqzFv |
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=Conformational+Selection+in+Glycomimetics%3A+Human+Galectin%E2%80%901+Only+Recognizes+syn+%E2%80%90+%CE%A8+%E2%80%90Type+Conformations+of+%CE%B2%E2%80%901%2C3%E2%80%90Linked+Lactose+and+Its+C+%E2%80%90Glycosyl+Derivative&rft.jtitle=Chemistry+%3A+a+European+journal&rft.au=Vidal%2C+Paloma&rft.au=Rold%C3%B3s%2C+Virginia&rft.au=Fern%C3%A1ndez%E2%80%90Alonso%2C+Mar%C3%ADa+del+Carmen&rft.au=Vauzeilles%2C+Boris&rft.date=2013-10-18&rft.issn=0947-6539&rft.eissn=1521-3765&rft.volume=19&rft.issue=43&rft.spage=14581&rft.epage=14590&rft_id=info:doi/10.1002%2Fchem.201301244&rft.externalDBID=n%2Fa&rft.externalDocID=10_1002_chem_201301244 |
thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0947-6539&client=summon |
thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0947-6539&client=summon |
thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0947-6539&client=summon |