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Rethinking Cysteine Protective Groups: S ‐Alkylsulfonyl‐ l ‐Cysteines for Chemoselective Disulfide Formation
Author(s) -
Schäfer Olga,
Huesmann David,
Muhl Christian,
Barz Matthias
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201604391
Subject(s) - cysteine , chemistry , peptide , disulfide bond , derivative (finance) , cleavage (geology) , amino acid , polymerization , thiol , stereochemistry , peptide synthesis , combinatorial chemistry , biochemistry , organic chemistry , polymer , enzyme , geotechnical engineering , fracture (geology) , financial economics , engineering , economics
The ability to reversibly cross‐link proteins and peptides grants the amino acid cysteine its unique role in nature as well as in peptide chemistry. We report a novel class of S ‐alkylsulfonyl‐ l ‐cysteines and N ‐carboxy anhydrides (NCA) thereof for peptide synthesis. The S ‐alkylsulfonyl group is stable against amines and thus enables its use under Fmoc chemistry conditions and the controlled polymerization of the corresponding NCAs yielding well‐defined homo‐ as well as block co‐polymers. Yet, thiols react immediately with the S ‐alkylsulfonyl group forming asymmetric disulfides. Therefore, we introduce the first reactive cysteine derivative for efficient and chemoselective disulfide formation in synthetic polypeptides, thus bypassing additional protective group cleavage steps.