- Mycothiol synthesis by an anomerization reaction through endocyclic cleavage
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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.
- Manabe, Shino,Ito, Yukishige
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p. 328 - 333
(2016/04/05)
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- Desymmetrization of 2,4,5,6-tetra-o-benzyl-d-myo-inositol for the synthesis of mycothiol
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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%.
- Chung, Chuan-Chung,Zulueta, Medel Manuel L.,Padiyar, Laxmansingh T.,Hung, Shang-Cheng
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p. 5496 - 5499
(2011/12/22)
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- Intramolecular α-glucosaminidation: Synthesis of mycothiol
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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.
- Ajayi, Kehinde,Thakur, Vinay V.,Lapo, Robert C.,Knapp, Spencer
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supporting information; experimental part
p. 2630 - 2633
(2010/08/22)
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- Mycothiol disulfide reductase: Solid phase synthesis and evaluation of alternative substrate analogues
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A solid phase synthesis of des-myo-inositol mycothiol disulfide and its alpha-configured methyl- and benzyl-glycoside derivatives has been developed. Kinetic characterisation of these compounds has demonstrated their viability as alternative substrates for use in mycothiol disulfide reductase enzyme assays. This journal is The Royal Society of Chemistry.
- Stewart, Matthew J. G.,Jothivasan, Vishnu Karthik,Rowan, Andrew S.,Wagg, Jennifer,Hamilton, Chris J.
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p. 385 - 390
(2008/10/09)
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- First Total Synthesis of Mycothiol and Mycothiol Disulfide
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(Matrix presented) The first total synthesis of mycothiol and mycothiol disulfide was achieved by linking D-2,3,4,5,6-penta-O-acetyl-myo-inositol, O-(3,4,6-tri-O-acetyl)-2-azido-2-deoxy-α,β-D-glucopyranosyl) trichloroacetimidate, and N,S-diacetyl-L-cysteine and deprotecting peracetylated mycothiol. The first full spectral characterization is reported for underivatized mycothiol. The structure of mycothiol was confirmed by spectral analysis of the known bimane derivative.
- Lee, Sungwon,Rosazza, John P. N.
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p. 365 - 368
(2007/10/03)
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