Chemoselective F-18-incorporation into pyridyl acyltrifluoroborates for rapid radiolabelling of peptides and proteins at room temperature
A new prosthetic group is reported for F-18-labelling of peptides and proteins based on the chemoselective ligation of potassium acyltrifluoroborates (KATs) and hydroxylamines without any detectable F-18/F-19 isotope exchange at the acyltrifluoroborate moiety. The new building block is appended via...
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| Published in | Chemical communications (Cambridge, England) Vol. 56; no. 5; pp. 723 - 726 |
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| Main Authors | , , , , , , , , , |
| Format | Journal Article |
| Language | English |
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Royal Soc Chemistry
16.01.2020
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| Abstract | A new prosthetic group is reported for F-18-labelling of peptides and proteins based on the chemoselective ligation of potassium acyltrifluoroborates (KATs) and hydroxylamines without any detectable F-18/F-19 isotope exchange at the acyltrifluoroborate moiety. The new building block is appended via a common amide bond at room temperature with no need for protecting groups which enables an effective orthogonal F-18-radiolabelling. |
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| AbstractList | A new prosthetic group is reported for F-18-labelling of peptides and proteins based on the chemoselective ligation of potassium acyltrifluoroborates (KATs) and hydroxylamines without any detectable F-18/F-19 isotope exchange at the acyltrifluoroborate moiety. The new building block is appended via a common amide bond at room temperature with no need for protecting groups which enables an effective orthogonal F-18-radiolabelling. |
| Author | Bode, Jeffrey W. Chiotellis, Aristeidis Tanriver, Matthias White, Christopher J. Betzel, Thomas Song, Haewon Da Ros, Sara Schibli, Roger Ametamey, Simon M. Ahmed, Hazem |
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| Cites_doi | 10.1021/acs.accounts.5b00398 10.1002/chem.201405829 10.1021/ja044996f 10.1053/j.semnuclmed.2017.07.001 10.1038/nprot.2006.264 10.1021/acs.chemrev.5b00493 10.1039/c2md20105d 10.1021/acs.bioconjchem.6b00561 10.1021/cb5006728 10.1021/acs.chemrev.7b00090 10.1038/nprot.2015.090 10.1021/acscentsci.7b00432 10.1021/bc500475e 10.1021/jm9015813 10.1021/ja5018442 10.1039/c6cc01982j 10.2174/0929867323666160418114826 10.1088/0031-9155/51/13/R08 10.1007/s13139-015-0377-6 10.1021/ja8053805 10.7150/thno.5984 10.1002/anie.201406258 10.1002/anie.201201077 10.1021/cr0782426 10.1039/c0ob00255k 10.1021/bc050086r 10.1038/nchem.2693 10.1002/ejoc.201700970 10.1158/0008-5472.CAN-10-1584 10.1021/bc034107y |
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| Keywords | ORGANOTRIFLUOROBORATE DESIGN RADIOCHEMISTRY LIGATION CLICK-CHEMISTRY BIOMOLECULES EXCHANGE WATER |
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| Title | Chemoselective F-18-incorporation into pyridyl acyltrifluoroborates for rapid radiolabelling of peptides and proteins at room temperature |
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