Preparation of Erythromycin Analogs Having Functional Groups at C-15

Chemobiosynthesis has been used to prepare analogs of erythromycins having unique functional groups at the 15-position. Using diketide thioester feeding to genetically engineered Streptomyces coelicolor, analogs of 6-deoxyerythronolide B were prepared having 15-fluoro, 15-chloro, and 15-azido groups...

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Published inJournal of antibiotics Vol. 59; no. 7; pp. 392 - 401
Main Authors Ashley, Gary W., Burlingame, Mark, Desai, Ruchir, Fu, Hong, Leaf, Tim, Licari, Peter J., Tran, Chau, Abbanat, Darren, Bush, Karen, Macielag, Mark
Format Journal Article
LanguageEnglish
Published TOKYO Japan Antibiotics Research Assoc 01.07.2006
Nature Publishing Group
Subjects
Biotechnology & Applied Microbiology
Erythromycin - analogs & derivatives
Erythromycin - biosynthesis
Erythromycin - chemistry
Genetic Engineering
Immunology
Life Sciences & Biomedicine
Microbiology
Molecular Structure
Pharmacology & Pharmacy
Physicochemical properties
Science & Technology
Streptomyces coelicolor - genetics
Streptomyces coelicolor - metabolism
DIRECTED BIOSYNTHESIS
erythromycin
polyketide
antibacterial
azide
genetic engineering
fluorine
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Summary:Chemobiosynthesis has been used to prepare analogs of erythromycins having unique functional groups at the 15-position. Using diketide thioester feeding to genetically engineered Streptomyces coelicolor, analogs of 6-deoxyerythronolide B were prepared having 15-fluoro, 15-chloro, and 15-azido groups. Bioconversion using a genetically engineered mutant of Saccharopolyspora erythraea was used to produce 15-fluoroerythromycin A and 15-azidoerythromycin A. These new erythromycin analogs provide antibacterial macrolides with unique physicochemical properties and functional groups that allow for selective derivatization.
Bibliography:ObjectType-Article-1
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ISSN:0021-8820
1881-1469
DOI:10.1038/ja.2006.56