Chemical Conversion of Nocathiacin I to Nocathiacin II and a Lactone Analogue of Glycothiohexide α

Nocathiacin I (1) was converted to its deoxy indole analogue, nocathiacin II (2), another natural product, by a unique and facile chemical process. This process was applied to nocathiacin IV (4), generating the lactone analogue of glycothiohexide α (5), which was also prepared from nocathiacin II by...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2005-04, Vol.68 (4), p.550-553
Main Authors: Connolly, Timothy P, Regueiro-Ren, Alicia, Leet, John E, Springer, Dane M, Goodrich, Jason, Huang, Xiaohua (Stella), Pucci, Michael J, Clark, Junius M, Bronson, Joanne J, Ueda, Yasutsugu
Format: Article
Language:English
Subjects:
Animals
Anti-Bacterial Agents - chemistry
Anti-Bacterial Agents - pharmacology
Antibacterial agents
Antibiotics. Antiinfectious agents. Antiparasitic agents
Biological and medical sciences
Disease Models, Animal
Medical sciences
Mice
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Peptides - chemistry
Peptides - pharmacology
Peptides, Cyclic - chemistry
Peptides, Cyclic - pharmacology
Pharmacology. Drug treatments
Thiazoles - chemistry
Thiazoles - pharmacology
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Summary:Nocathiacin I (1) was converted to its deoxy indole analogue, nocathiacin II (2), another natural product, by a unique and facile chemical process. This process was applied to nocathiacin IV (4), generating the lactone analogue of glycothiohexide α (5), which was also prepared from nocathiacin II by a mild hydrolytic process. In contrast to glycothiohexide α (3), this lactone analogue (5) was found to exhibit in vivo antibacterial efficacy in an animal (mouse) infection model.
ISSN:0163-3864
1520-6025
DOI:10.1021/np040225d