Rapid formal hydrolysis of peptide-αthioesters

Zachary P. Gates; Jules R. Stephan; Dong Jun Lee; Stephen B. H. Kent

doi:10.1039/C2CC38229F

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Rapid formal hydrolysis of peptide-^αthioesters†

Zachary P. Gates,*^a Jules R. Stephan,^a Dong Jun Lee^a and Stephen B. H. Kent^a

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^a Department of Chemistry, University of Chicago, Chicago, IL, USA
E-mail: skent@uchicago.edu
Tel: +1 773 702 4912

Abstract

In the presence of 2-mercaptoethanol peptide-^αthioesters undergo smooth conversion to their corresponding peptide-^αcarboxylates. This general and operationally simple reaction extends the utility of a promising new strategy for cleaving resin-bound Boc/benzyl-protected peptides without the use of hydrogen fluoride.

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Article information

DOI: https://doi.org/10.1039/C2CC38229F
Article type: Communication
Submitted: 14 Nov 2012
Accepted: 29 Nov 2012
First published: 29 Nov 2012

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Chem. Commun., 2013,49, 786-788

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Rapid formal hydrolysis of peptide-^αthioesters

Z. P. Gates, J. R. Stephan, D. J. Lee and S. B. H. Kent, Chem. Commun., 2013, 49, 786 DOI: 10.1039/C2CC38229F

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