Application of a novel thioesterification reaction to the synthesis of chemokine CCL27 by the modified thioester method

Organic & Biomolecular Chemistry Pub Date: 2008-03-31 DOI: 10.1039/B800884A

Abstract

Aryl thioesters of peptide segments were prepared by the conventional 9-fluorenylmethoxycarbonyl (Fmoc) strategy using a novel N-alkyl cysteine (NAC)-assisted thioesterification reaction. The peptide carrying NAC at its C-terminus was prepared by the Fmoc strategy and converted to the aryl thioester by 4-mercaptophenylacetic acid (MPAA) treatment without significant side reactions. The peptide thioester was used for the efficient preparation of 95-amino acid (AA) chemokine CCL27 by an Ag+-free thioester method.

Graphical abstract: Application of a novel thioesterification reaction to the synthesis of chemokine CCL27 by the modified thioester method
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