Jump to main content
Jump to site search


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

Author affiliations

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

Back to tab navigation

Supplementary files

Article information


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

Org. Biomol. Chem., 2020, Advance Article
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, Advance Article , DOI: 10.1039/D0OB01475C

Social activity

Search articles by author

Spotlight

Advertisements