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Issue 18, 2017
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Tandem deprotection/coupling for peptide synthesis in water at room temperature

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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

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Publication details

The article was received on 29 May 2017, accepted on 21 Jul 2017 and first published on 24 Jul 2017


Article type: Communication
DOI: 10.1039/C7GC01575E
Citation: Green Chem., 2017,19, 4263-4267
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    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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