Preparation and In Vitro Antibacterial Activity of 6-O-Methylerythromycin D

The commercial success of 6-O-methylerythromycin A (clarithromycin) has prompted further study of alkylation reactions in macrolide synthesis. While synthetic methods for 6-O-methylation of erythromycin A are well-known, appropriate processes for methylation of structurally simpler erythromycin A pr...

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Published inJournal of antibiotics Vol. 52; no. 9; pp. 831 - 834
Main Authors GRACEY, H. EUGENE, MONTGOMERY, STEPHEN H., LIU, JIH-HUA, NILIUS, ANGELA, CELEBUSKI, JOSEPH E.
Format Journal Article
LanguageEnglish
Published TOKYO JAPAN ANTIBIOTICS RESEARCH ASSOCIATION 1999
JAPAN ANTIBIOT RES ASSN
Subjects
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - pharmacology
Biotechnology & Applied Microbiology
Erythromycin - analogs & derivatives
Erythromycin - chemical synthesis
Erythromycin - pharmacology
Immunology
Life Sciences & Biomedicine
Methylerythromycin D
Microbial Sensitivity Tests
Microbiology
Pharmacology & Pharmacy
Science & Technology
CHEMICAL MODIFICATION
ERYTHROMYCIN-A
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Summary:The commercial success of 6-O-methylerythromycin A (clarithromycin) has prompted further study of alkylation reactions in macrolide synthesis. While synthetic methods for 6-O-methylation of erythromycin A are well-known, appropriate processes for methylation of structurally simpler erythromycin A precursors have not been reported in the literature. Erythromycin D is a biosynthetic precursor of erythromycin A, lacking the 12-hydroxy group and the 3"-methoxymethyl group of erythromycin A. We now report the synthesis and in vitro antibacterial activity of 6-O-methylerythromycin D.
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ISSN:0021-8820
1881-1469
DOI:10.7164/antibiotics.52.831