1228173-37-2Relevant academic research and scientific papers
Mycothiol synthesis by an anomerization reaction through endocyclic cleavage
Manabe, Shino,Ito, Yukishige
supporting information, p. 328 - 333 (2016/04/05)
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.
Desymmetrization of 2,4,5,6-tetra-o-benzyl-d-myo-inositol for the synthesis of mycothiol
Chung, Chuan-Chung,Zulueta, Medel Manuel L.,Padiyar, Laxmansingh T.,Hung, Shang-Cheng
supporting information; experimental part, p. 5496 - 5499 (2011/12/22)
An efficient chemical synthesis of mycothiol involving the regioselective ketopinyl desymmetrization of 2,4,5,6-tetrabenzylated d-myo-inositol as the key step is described. Together with a highly α-stereoselective d-glucosaminylation, the whole procedure was accomplished in eight steps with an overall yield of 40%.
Intramolecular α-glucosaminidation: Synthesis of mycothiol
Ajayi, Kehinde,Thakur, Vinay V.,Lapo, Robert C.,Knapp, Spencer
supporting information; experimental part, p. 2630 - 2633 (2010/08/22)
A protected cyclitol aglycon was tethered to an (N-arylsulfonyl)glucosamine donor by a methylene linker; the exclusively α-selective intramolecular glycosyation reaction was then initiated by electrophilic activation of the thioglycoside donor portion. Further transformations of the glycosylation product to give the M. tuberculosis detoxifier mycothiol and its oxidized congener, the disulfide mycothione, are detailed.
