Mycothiol synthesis by an anomerization reaction through endocyclic cleavage

Shino Manabe, Yukishige Ito

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)328-333
Number of pages6
JournalBeilstein Journal of Organic Chemistry
Volume12
DOIs
Publication statusPublished - 2016 Feb 22
Externally publishedYes

Keywords

  • Aminoglycoside
  • Anomerization
  • Endocyclic cleavage reaction
  • Inositol
  • Mycothiol

ASJC Scopus subject areas

  • Organic Chemistry

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