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Issue 42, 2020
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Deprotection of S-acetamidomethyl cysteine with copper(ii) and 1,2-aminothiols under aerobic conditions

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Abstract

Ring-opening by CuSO4 of a 1,3-thiazolidine carbonyl structure (Thz) as an N-terminal cysteine (Cys) residue revealed that an intramolecular S-acetamidomethyl cysteine (Cys(Acm)) can also be deprotected with concomitant formation of a disulphide bond connecting the two Cys residues. A mechanistic study on the disulphide formation led to a general protocol for deprotection of the S-Acm group by CuSO4 and a 1,2-aminothiol under aerobic conditions. Application of this new deprotection reaction allowed for the synthesis of Apamin, a peptide with two-disulphides in a one-pot/stepwise disulphide-bridging procedure.

Graphical abstract: Deprotection of S-acetamidomethyl cysteine with copper(ii) and 1,2-aminothiols under aerobic conditions

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Article information


Submitted
17 Jul 2020
Accepted
19 Aug 2020
First published
20 Aug 2020

Org. Biomol. Chem., 2020,18, 8638-8645
Article type
Paper

Deprotection of S-acetamidomethyl cysteine with copper(II) and 1,2-aminothiols under aerobic conditions

D. Kobayashi, N. Naruse, M. Denda, A. Shigenaga and A. Otaka, Org. Biomol. Chem., 2020, 18, 8638
DOI: 10.1039/D0OB01475C

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