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Issue 25, 2015

Peptide 2-formylthiophenol esters do not proceed through a Ser/Thr ligation pathway, but participate in a peptide aminolysis to enable peptide condensation and cyclization

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Abstract

Peptide thiol salicylaldehyde (SAL) esters unexpectedly do not follow a Ser/Thr ligation pathway to react with peptides containing N-terminal Ser/Thr, but proceed towards a peptide aminolysis in DMSO. The reaction takes place even at a low substrate concentration (1 mM). The method has been successfully used to synthesize several natural cyclic peptides, with a high ratio of monocyclic to dimeric products.

Graphical abstract: Peptide 2-formylthiophenol esters do not proceed through a Ser/Thr ligation pathway, but participate in a peptide aminolysis to enable peptide condensation and cyclization

Supplementary files

Article information


Submitted
24 Apr 2015
Accepted
08 May 2015
First published
14 May 2015

Org. Biomol. Chem., 2015,13, 6922-6926
Article type
Communication
Author version available

Peptide 2-formylthiophenol esters do not proceed through a Ser/Thr ligation pathway, but participate in a peptide aminolysis to enable peptide condensation and cyclization

C. L. Tung, C. T. T. Wong and X. Li, Org. Biomol. Chem., 2015, 13, 6922 DOI: 10.1039/C5OB00825E

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