Issue 18, 2017

Tandem deprotection/coupling for peptide synthesis in water at room temperature

Abstract

A tandem deprotection/coupling sequence is reported for solution-phase peptide synthesis in water under micellar catalysis conditions using the designer surfactant TPGS-750-M. Cbz deprotection followed by peptide coupling in the presence of COMU and 2,6-lutidine afforded polypeptides containing up to 10 amino acid residues. A broad scope characterizes this new technology. No epimerization has been detected. The associated E Factors, as a measure of “greenness” and known to be extremely high for peptide couplings, have been reduced to less than 10 due to the step-economy and minimal amounts of organic solvent needed for product extraction.

Graphical abstract: Tandem deprotection/coupling for peptide synthesis in water at room temperature

Supplementary files

Article information

Article type
Communication
Submitted
29 may 2017
Accepted
21 iyl 2017
First published
24 iyl 2017

Green Chem., 2017,19, 4263-4267

Tandem deprotection/coupling for peptide synthesis in water at room temperature

M. Cortes-Clerget, J. Berthon, I. Krolikiewicz-Renimel, L. Chaisemartin and B. H. Lipshutz, Green Chem., 2017, 19, 4263 DOI: 10.1039/C7GC01575E

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