PMID: 11929223Apr 4, 2002Paper

Total synthesis and proof of structure of mycothiol bimane

Journal of the American Chemical Society
Gillian M NicholasCarole A Bewley

Abstract

Mycothiol is a low-molecular weight thiol produced by actinomycetes that serves to protect these organisms from oxidative stress and alkylating agents. We report the total synthesis of mycothiol bimane (1) which is a commonly isolated derivative of mycothiol. The synthesis confirms the original structure assignment and unambiguously establishes the absolute stereochemistry of mycothiol to be 1-d-myo-inosityl 2-deoxy-2-(N-acetamido-l-cysteinamido)-alpha-d-glucopyranoside.

Citations

Jul 17, 2008·Archives of Microbiology·Gerald L NewtonRobert C Fahey
Oct 22, 2005·Applied Microbiology and Biotechnology·Zbigniew J Witczak, James M Culhane
May 19, 2007·Carbohydrate Research·Rikard SlättegårdStefan Oscarson
Nov 22, 2002·Organic Letters·Spencer KnappCarole A Bewley
Jan 30, 2004·Organic Letters·Sungwon Lee, John P N Rosazza
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