Total Synthesis and Proof of Structure of Mycothiol Bimane

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 stru...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2002-04, Vol.124 (14), p.3492-3493
Main Authors: Nicholas, Gillian M, Kováč, Pavol, Bewley, Carole A
Format: Article
Language:English
Subjects:
Bridged Bicyclo Compounds, Heterocyclic - chemical synthesis
Bridged Bicyclo Compounds, Heterocyclic - chemistry
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Chemistry
Circular Dichroism
Cysteine
Disaccharides - chemical synthesis
Disaccharides - chemistry
Exact sciences and technology
Glycopeptides
Inositol
Organic chemistry
Preparations and properties
Pyrazoles - chemical synthesis
Pyrazoles - chemistry
Sulfhydryl Compounds - chemical synthesis
Sulfhydryl Compounds - chemistry
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Summary: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)-α-d-glucopyranoside.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja017891a