Microbial Glycosylation of Macrolide Antibiotics by Streptomyces hygroscopicus ATCC 31080 and Distribution of a Macrolide Glycosyl Transferase in Several Streptomyces Strains

In the course of our microbial transformation study on erythromycin derivatives, Streptomyces hygroscopicus ATCC 31080, which produces a poly ether antibiotic carriomycin, was found to transform erythromycin derivatives to their inactivated derivatives. The structures of inactivated derivatives prep...

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Bibliographic Details
Published in:Journal of antibiotics 1996/11/25, Vol.49(11), pp.1110-1118
Main Authors: SASAKI, Jon, MIZOUE, KAZUTOSHI, MORIMOTO, SHIGEO, OMURA, SADAFUMI
Format: Article
Language:English
Subjects:
Anti-Bacterial Agents - metabolism
Anti-Bacterial Agents - pharmacology
Antibacterial agents
Antibiotics. Antiinfectious agents. Antiparasitic agents
Biological and medical sciences
Erythromycin - metabolism
Glycosylation
Medical sciences
Microbial Sensitivity Tests
Pharmacology. Drug treatments
Streptomyces - enzymology
Streptomyces hygroscopicus
Transferases - metabolism
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Summary:In the course of our microbial transformation study on erythromycin derivatives, Streptomyces hygroscopicus ATCC 31080, which produces a poly ether antibiotic carriomycin, was found to transform erythromycin derivatives to their inactivated derivatives. The structures of inactivated derivatives prepared by enzyme reaction using the cell extract, UDP-glucose (or UDP-galactose) and Mg2+ (or Mn2+) were elucidated on the basis of analysis of their spectral data to be the compounds glycosylated at C-2' of a desosamine moiety, indicating that the enzyme is a macrolide glycosyl transferase (MGT). The MGT activity of cell extract from S. antibiotieus ATCC 11891, a producing organism of oleandomycin, could be distinguished from that of ATCC 31080, based on the ability to glycosylate tylosin. We examined 32 actinomycete strains producing such polyketides as macrolide and polyether antibiotics, and found that 15 strains of Streptomyces have macrolide glycosyl transferase activity. It suggests that the MGTs have been distributed among at least polyketide producing Streptomyces strains.
ISSN:0021-8820
1881-1469
DOI:10.7164/antibiotics.49.1110