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Org Lett. 2004 Feb 5;6(3):365-8.

First total synthesis of mycothiol and mycothiol disulfide.

Author information

1
Division of Medicinal and Natural Products Chemistry, College of Pharmacy, and Center for Biocatalysis and Bioprocessing, The University of Iowa, Iowa City, Iowa 52242, USA.

Abstract

[reaction: see text] 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-alpha,beta-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.

PMID:
14748594
DOI:
10.1021/ol0362008
[Indexed for MEDLINE]

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