Synthesis of mycothiol, 1D-1-O-(2-[N-acetyl-l-cysteinyl]amino-2-deoxy-α-d-glucopyranosyl)-myo-inositol, principal low molecular mass thiol in the actinomycetes

• Published in: Bioorganic & medicinal chemistry Vol. 10; no. 4; pp. 875 - 881
• Main Authors: Jardine, M.Anwar, Spies, Hendrik S.C, Nkambule, Comfort M, Gammon, David W, Steenkamp, Daniel J
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Ltd 01.04.2002; Elsevier Science
• Subjects: Actinomycetales - chemistry; Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides; Carbohydrates. Nucleosides and nucleotides; Chemistry; Cysteine; Disaccharides - biosynthesis; Disaccharides - chemical synthesis; Disaccharides - metabolism; Exact sciences and technology; Glycopeptides; Inositol; Molecular Weight; Mycobacterium smegmatis - enzymology; Nuclear Magnetic Resonance, Biomolecular; Organic chemistry; Preparations and properties; Pyrazoles - chemical synthesis; Pyrazoles - metabolism; Sulfhydryl Compounds - chemical synthesis; Sulfhydryl Compounds - metabolism; Biosynthesis precursor; Cyclitol; Enantioselectivity; Chemical synthesis; Aminoglycoside; Disaccharide

Members of the actinomycetes produce 1D-1-O-(2-[N-acetyl-l-cysteinyl]amino-2-deoxy-α-d-glucopyranosyl)-myo-inositol or mycothiol 1 as principal low molecular mass thiol. Chemical synthesis of a biosynthetic precursor of mycothiol, the pseudodisaccharide 1D-1-O-(2-amino-2-deoxy-α-d-glucopyranosyl)-my...