A Thioethylalkylamido (TEA) Thioester Surrogate in the Synthesis

A Thioethylalkylamido (TEA) Thioester Surrogate in the Synthesis of a Cyclic Peptide via a Tandem Acyl Shift
Misako Taichi , Xinya Hemu , Yibo Qiu , and James P. Tam *
School of Biological Sciences, Nanyang Technological University, 60 Nanyang Drive, Singapore 637551
Org. Lett., Article ASAP
DOI: 10.1021/ol400801k
Publication Date (Web): May 13, 2013
Copyright © 2013 American Chemical Society

The cyclic cystine-knot peptide, kalata B1, was synthesized by employing a novel Fmoc-compatible thioethylalkylamido (TEA) thioester surrogate via an N–S acyl shift followed by a thiol-thioester exchange reaction. TEA thioester surrogate is cost-effective, conveniently prepared in one-step with starting materials, readily available from commercial sources, and highly efficient in preparing peptide thioesters.