Conformational analyses of mycothiol, a critical intracellular glycothiol in Mycobacteria

Carbohydrate Research
Christine E HandJohn F Honek

Abstract

Intracellular thiols are essential biomolecules, which play several critical roles in living organisms including controlling intracellular redox potential and acting as cofactors for several vital detoxification enzymes including S-transferases and formaldehyde dehydrogenases. The tripeptide gamma-L-glutamyl-L-cysteinylglycine, more commonly known as glutathione, is well known as the major intracellular thiol in eukaryotes and in some bacteria. However, glutathione is absent in the Actinomycetales bacteria such as Mycobacteria and Streptomyces and is believed to be replaced by 1-D-myo-inosityl-2-(N-acetyl-L-cysteinyl)amido-2-deoxy-alpha-D-glucopyranoside, mycothiol, in these organisms. Although much is known about the chemistry and biochemistry of glutathione, currently much less is known concerning mycothiol and its properties. The structure of mycothiol is composed of a glycoside linkage between myo-inositol and D-glucosamine with an N-acetyl-L-cysteine linked to the 2'-amino group of the d-glucosamine moiety. Mycothiol is currently of intense interest due to its essential role in the cellular physiology of Mycobacteria, such as Mycobacterium tuberculosis, and its possible role in antimycobacterial drug resistance. A detailed...Continue Reading

References

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Citations

Sep 6, 2008·Microbiology and Molecular Biology Reviews : MMBR·Gerald L NewtonRobert C Fahey
Feb 12, 2011·Seminars in Cell & Developmental Biology·Uthaiwan Suttisansanee, John F Honek
Nov 26, 2008·Natural Product Reports·Vishnu Karthik Jothivasan, Chris J Hamilton
Jul 6, 2014·Chembiochem : a European Journal of Chemical Biology·Bryan D CoxJames P Snyder
Mar 16, 2016·Beilstein Journal of Organic Chemistry·Shino Manabe, Yukishige Ito

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