Biosynthesis of the manumycin group antibiotics
- Universitaet Goettingen (West Germany)
- Kitasato Univ., Tokyo (Japan)
- Ohio State Univ., Columbus (USA)
- Univ. of Washington, Seattle (USA)
The biosynthesis of the manumycin group antibiotics manumycin (1) and asukamycin (2) was studied in Streptomyces parvulus Tue 64 and Streptomyces nodosus ssp. asukaensis ATCC 29,757 by using radioactive and stable isotope tracer techniques and high-field NMR spectroscopy. The results have demonstrated that the central, multifunctional mC{sub 7}N unit typical of this group of antibiotics, which serves as the starter unit for a short polyketide chain, is biosynthesized from a C{sub 4} Krebs cycle and a C{sub 3} triose phosphate pool intermediate by a new pathway, distinct from the shikimate, polyketide, or pentose phosphate routes leading to other mC{sub 7}N units in nature. The C{sub 5} unit in both 1 and 2 arises by a novel intramolecular cyclization of 5-aminolevulinic acid, and a cyclohexane ring and the adjacent carbon in 2 arise from the seven carbon atoms of shikimic acid. The side chains of both antibiotics represent typical polyketide-derived moieties, differing with respect to their combinations of starter and elongation units.
- OSTI ID:
- 6793822
- Journal Information:
- Journal of the American Chemical Society; (USA), Vol. 112:10; ISSN 0002-7863
- Country of Publication:
- United States
- Language:
- English
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