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Literature DB >> 20443569

Intramolecular alpha-glucosaminidation: synthesis of mycothiol.

Kehinde Ajayi¹, Vinay V Thakur, Robert C Lapo, Spencer Knapp.

Abstract

A protected cyclitol aglycon was tethered to an (N-arylsulfonyl)glucosamine donor by a methylene linker; the exclusively alpha-selective intramolecular glycosylation 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.

Entities: Chemical Disease Gene Species

Mesh：

Substances：

Year: 2010 PMID： 20443569 PMCID： PMC2892847 DOI： 10.1021/ol1008334

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

29 in total

1. Biochemistry of the initial steps of mycothiol biosynthesis.

Authors: Gerald L Newton; Philong Ta; Krzysztof P Bzymek; Robert C Fahey
Journal: J Biol Chem Date: 2006-08-28 Impact factor: 5.157

2. Differential antibiotic susceptibilities of starved Mycobacterium tuberculosis isolates.

Authors: Zhifang Xie; Noman Siddiqi; Eric J Rubin
Journal: Antimicrob Agents Chemother Date: 2005-11 Impact factor: 5.191

Review 3. Drugs for bad bugs: confronting the challenges of antibacterial discovery.

Authors: David J Payne; Michael N Gwynn; David J Holmes; David L Pompliano
Journal: Nat Rev Drug Discov Date: 2006-12-08 Impact factor: 84.694

Review 4. Intramolecular aglycon delivery.

Authors: Ian Cumpstey
Journal: Carbohydr Res Date: 2008-04-29 Impact factor: 2.104

5. Total synthesis and structural revision of TMG-chitotriomycin, a specific inhibitor of insect and fungal beta-N-acetylglucosaminidases.

Authors: You Yang; Yao Li; Biao Yu
Journal: J Am Chem Soc Date: 2009-09-02 Impact factor: 15.419

6. Total synthesis and proof of structure of mycothiol bimane.

Authors: Gillian M Nicholas; Pavol Kovác; Carole A Bewley
Journal: J Am Chem Soc Date: 2002-04-10 Impact factor: 15.419

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

Authors: M Anwar Jardine; Hendrik S C Spies; Comfort M Nkambule; David W Gammon; Daniel J Steenkamp
Journal: Bioorg Med Chem Date: 2002-04 Impact factor: 3.641

Intramolecular alpha-glucosaminidation: synthesis of mycothiol.

1. Biochemistry of the initial steps of mycothiol biosynthesis.

2. Differential antibiotic susceptibilities of starved Mycobacterium tuberculosis isolates.

Review 3. Drugs for bad bugs: confronting the challenges of antibacterial discovery.

Review 4. Intramolecular aglycon delivery.

5. Total synthesis and structural revision of TMG-chitotriomycin, a specific inhibitor of insect and fungal beta-N-acetylglucosaminidases.

6. Total synthesis and proof of structure of mycothiol bimane.

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

8. Low-molecular-weight thiols in streptomycetes and their potential role as antioxidants.

9. Mycothiol disulfide reductase: solid phase synthesis and evaluation of alternative substrate analogues.

Review 10. Biosynthesis and functions of mycothiol, the unique protective thiol of Actinobacteria.

1. Metabolic coupling of two small-molecule thiols programs the biosynthesis of lincomycin A.

2. Mycothiol synthesis by an anomerization reaction through endocyclic cleavage.