Invited Speaker 7th Modern Solid Phase Peptide Synthesis & Its Applications Symposium 2019

Fmoc-Cys(Msbh) – a sophisticated building block for cysteine-rich peptides. A journey from discovery through to large scale production. (#34)

Thomas Bruckdorfer 1 , Markus Weishaupt 1 , Haixiang Zhang 2
  1. Iris Biotech GmbH, Marktredwitz, Germany
  2. Iris Biotech Laboratories GmbH, Marktredwitz, Germany

A safety-catch cysteine protecting group, S-4,4’-dimethylsulfinylbenzhydryl (Msbh), has been gained increasing interest in the last past, in order to expand the capabilities of synthetic strategies for the regioselective formation of disulfide bonds in cysteine-rich peptides, e.g. sequences with up to four disulfide bonds, or containing disulfide bonds next to free cysteines. The orthogonality of Msbh towards Fmoc, Boc and Alloc removal conditions promoted this cysteine derivative to a broadly used building block for challenging peptide sequences in bulk scale peptide synthesis. We describe how route of synthesis and conditions changes from discovery and use in research applications to industrial scale with a focus on production efficiency, economics, and sustainability.

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