Mycothiol synthesis by an anomerization reaction through endocyclic cleavage

Shino Manabe; Yukishige Ito

doi:10.3762/bjoc.12.35

Mycothiol synthesis by an anomerization reaction through endocyclic cleavage

Shino Manabe, Yukishige Ito

Research output: Contribution to journal › Article › peer-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 language	English
Pages (from-to)	328-333
Number of pages	6
Journal	Beilstein Journal of Organic Chemistry
Volume	12
DOIs	https://doi.org/10.3762/bjoc.12.35
Publication status	Published - 2016 Feb 22
Externally published	Yes

Keywords

Aminoglycoside
Anomerization
Endocyclic cleavage reaction
Inositol
Mycothiol

ASJC Scopus subject areas

Organic Chemistry

UN SDGs

This output contributes to the following Sustainable Development Goal(s)

Access to Document

10.3762/bjoc.12.35

Fingerprint Dive into the research topics of 'Mycothiol synthesis by an anomerization reaction through endocyclic cleavage'. Together they form a unique fingerprint.

Cite this

@article{344729ec673c4bb6a9e24edf2b18ef08,

title = "Mycothiol synthesis by an anomerization reaction through endocyclic cleavage",

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.",

keywords = "Aminoglycoside, Anomerization, Endocyclic cleavage reaction, Inositol, Mycothiol",

author = "Shino Manabe and Yukishige Ito",

note = "Publisher Copyright: {\textcopyright} 2016 Manabe and Ito.",

year = "2016",

month = feb,

day = "22",

doi = "10.3762/bjoc.12.35",

language = "English",

volume = "12",

pages = "328--333",

journal = "Beilstein Journal of Organic Chemistry",

issn = "1860-5397",

publisher = "Beilstein-Institut Zur Forderung der Chemischen Wissenschaften",

}

TY - JOUR

T1 - Mycothiol synthesis by an anomerization reaction through endocyclic cleavage

AU - Manabe, Shino

AU - Ito, Yukishige

PY - 2016/2/22

Y1 - 2016/2/22

N2 - 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.

AB - 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.

KW - Aminoglycoside

KW - Anomerization

KW - Endocyclic cleavage reaction

KW - Inositol

KW - Mycothiol

UR - http://www.scopus.com/inward/record.url?scp=84962252545&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84962252545&partnerID=8YFLogxK

U2 - 10.3762/bjoc.12.35

DO - 10.3762/bjoc.12.35

M3 - Article

AN - SCOPUS:84962252545

VL - 12

SP - 328

EP - 333

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

SN - 1860-5397

ER -

Mycothiol synthesis by an anomerization reaction through endocyclic cleavage

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

Access to Document

Other files and links

Cite this