Mycothiol synthesis by an anomerization reaction through endocyclic cleavage

Mycothiol is found in Gram-positive bacteria, where it helps in maintaining a reducing intracellular environment and it plays an important role in protecting the cell from toxic chemicals. The inhibition of the mycothiol biosynthesis is considered as a treatment for tuberculosis. Mycothiol contains...

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Bibliographic Details
Published in:Beilstein journal of organic chemistry 2016-02, Vol.12 (1), p.328-333
Main Authors: Manabe, Shino, Ito, Yukishige
Format: Article
Language:English
Subjects:
aminoglycoside
anomerization
Chemistry
endocyclic cleavage reaction
inositol
Letter
mycothiol
Tuberculosis
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Summary:Mycothiol is found in Gram-positive bacteria, where it helps in maintaining a reducing intracellular environment and it plays an important role in protecting the cell from toxic chemicals. The inhibition of the mycothiol biosynthesis is considered as a treatment for tuberculosis. Mycothiol contains an α-aminoglycoside, which is difficult to prepare stereoselectively by a conventional glycosylation reaction. In this study, mycothiol was synthesized by an anomerization reaction from an easily prepared β-aminoglycoside through endocyclic cleavage.
ISSN:1860-5397
2195-951X
1860-5397
DOI:10.3762/bjoc.12.35