Journal article
HF-Free Boc synthesis of peptide thioesters for ligation and cyclization
- Abstract:
- We have developed a convenient method for the direct synthesis of peptide thioesters, versatile intermediates for peptide ligation and cyclic peptide synthesis. The technology uses a modified Boc SPPS strategy that avoids the use of anhydrous HF. Boc in situ neutralization protocols are used in combination with Merrifield hydroxymethyl resin and TFA/TMSBr cleavage. Avoiding HF extends the scope of Boc SPPS to post-translational modifications that are compatible with the milder cleavage conditions, demonstrated here with the synthesis of the phosphorylated protein CHK2. Peptide thioesters give easy, direct, access to cyclic peptides, illustrated by the synthesis of cyclorasin, a KRAS inhibitor.
- Publication status:
- Published
- Peer review status:
- Peer reviewed
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(Preview, Version of record, pdf, 1.6MB, Terms of use)
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(Preview, Supplementary materials, pdf, 1.8MB, Terms of use)
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- Publisher copy:
- 10.1002/anie.201607657
Authors
- Publisher:
- Wiley
- Journal:
- Angewandte Chemie International Edition More from this journal
- Volume:
- 55
- Issue:
- 42
- Pages:
- 13174-13179
- Publication date:
- 2016-10-06
- Acceptance date:
- 2016-09-02
- DOI:
- EISSN:
-
1521-3773
- ISSN:
-
1433-7851
- Language:
-
English
- Keywords:
- Pubs id:
-
1111522
- Local pid:
-
pubs:1111522
- Deposit date:
-
2020-06-11
Terms of use
- Copyright holder:
- Raz et al.
- Copyright date:
- 2016
- Rights statement:
- © 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
- Licence:
- CC Attribution (CC BY)
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