Mycothiol synthesis by an anomerization reaction through endocyclic cleavage

• Shino Manabe and
• Yukishige Ito

Beilstein J. Org. Chem. 2016, 12, 328–333, doi:10.3762/bjoc.12.35

• Shino Manabe Yukishige Ito Synthetic Cellular Chemistry Lab, RIKEN, Hirosawa, Wako, Saitama 351-0198, Japan 10.3762/bjoc.12.35 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: anomerization; aminoglycoside; endocyclic cleavage reaction; inositol; mycothiol; Introduction Tuberculosis is an infectious disease and has had a high death rate over the past few decades [1][2][3][4]. The

Synthesis of 1,2-cis-2-C-branched aryl-C-glucosides via desulfurization of carbohydrate based hemithioacetals

• Henok H. Kinfe,
• Fanuel M. Mebrahtu,
• Mandlenkosi M. Manana,
• Kagiso Madumo and
• Mokela S. Sokamisa

Beilstein J. Org. Chem. 2015, 11, 583–588, doi:10.3762/bjoc.11.64

• to C-glycosides are 2-C-branched carbohydrates which are employed as bioisosters of the natural 2-acetamido glycoside derivatives. Gammon et al. prepared a series of 2-C-branched carbohydrates as potential inhibitors of enzymes implicated in the biosynthesis of mycothiol, Mycobacterium tuberculosis’s

• for the enzymes of Mycobacterium tuberculosis, in particular a deacetylase implicated in the biosynthesis of mycothiol, is under way and the results will be reported in the future. Single X-ray crystal structure of hemithioacetal 3a. (i) CAN, wet silica, KBr, CH2Cl2/CH3CN (1:1), rt, 30 min; (ii) a