Journal
ARCHIVES OF MICROBIOLOGY
Volume 193, Issue 2, Pages 95-103Publisher
SPRINGER
DOI: 10.1007/s00203-010-0648-7
Keywords
Cytochrome P450; Dihydrochalcomycin; Epoxidation; Gene disruption; Hydroxylation; Streptomyces
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Funding
- Ministry of Education, Science and Technology [20090082333, 2010-0015478]
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The macrolide antibiotics are biosynthesized by initial assembly of a macrolactone ring, followed by a series of post-polyketide (PKS) modifications. In general, the additional hydroxyl or epoxy groups are installed by cytochrome P450 enzymes, improving the bioactivity profile through structural diversification of natural products. The biosynthetic gene cluster for the 16-membered macrolide antibiotic dihydrochalcomycin (DHC) has been cloned from Streptomyces sp. KCTC 0041BP. Three cytochrome P450 genes are found in the DHC biosynthetic gene (ger) cluster. Two P450 enzymes were characterized from this cluster. Disruption of gerPI accumulated predominantly 12,13-de-epoxydihydrochalcomycin while disruption of gerPII accumulated 8-dehydroxy-12,13-de-epoxydihydrochalcomycin; DHC production was abolished in both cases. The results suggest that GerPII P450 catalyzes hydroxylation at the C-8 position followed by an epoxidation reaction catalyzed by GerPI P450 at the C-12-C-13 position.
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