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J Am Chem Soc. 2002 Apr 10;124(14):3492-3.

Total synthesis and proof of structure of mycothiol bimane.

Author information

1
Laboratories of Bioorganic Chemistry and Medicinal Chemistry, NIDDK, National Institutes of Health, Bethesda, Maryland 20892-0820, USA.

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.

PMID:
11929223
DOI:
10.1021/ja017891a
[Indexed for MEDLINE]

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