Studies on the biosynthesis of the antibiotic reductiomycin in Streptomyces xanthochromogenus
- Univ. of Washington, Seattle, WA (United States) Ohio State Univ., Columbus, OH (United States)
- Univ. of Washington, Seattle, WA (United States)
- Kitasato Univ. and Kitasato Inst., Tokyo (Japan)
The biosynthesis of the antibiotic reductiomycin (I) in Streptomyces xanthochromogenus was investigated by feeding experiments with radioactive and stable isotope-labeled precursors. NMR and mass spectroscopic analyses of the labeled I samples revealed that the acetoxy group comes from acetate, the 2-amino-3-hydroxycyclopent-2-enone moiety arises by a novel intramolecular cyclization of 5-aminolevulinic acid (ALA), and the dihydrofuranylacrylic moiety is formed by aromatic ring cleavage of a symmetrical product of the shikimate pathway. Both 4-hydroxy-[7-[sup 13]C]benzoic acid and 4-hydroxy-[7-[sup 13]C]benzaldehyde label 1 very efficiently, and deuterium from various positions in these precursors is incorporated into the predicted positions in the dihydrofuranylacrylic acid moiety of 1. The results are interpreted in terms of a dioxygenase mechanism for the ring cleavage reaction and pyridoxal phosphate catalysis for the ALA cyclization. 42 refs., 6 figs., 5 tabs.
- OSTI ID:
- 5136198
- Journal Information:
- Journal of the American Chemical Society; (United States), Vol. 115:26; ISSN 0002-7863
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
37 INORGANIC
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
ANTIBIOTICS
BIOSYNTHESIS
CATALYSIS
DEUTERIUM
EXPERIMENTAL DATA
FERMENTATION
LABELLED COMPOUNDS
MASS SPECTROSCOPY
NUCLEAR MAGNETIC RESONANCE
STREPTOMYCES
ANTI-INFECTIVE AGENTS
BACTERIA
BIOCONVERSION
DATA
DRUGS
HYDROGEN ISOTOPES
INFORMATION
ISOTOPES
LIGHT NUCLEI
MAGNETIC RESONANCE
MICROORGANISMS
NUCLEI
NUMERICAL DATA
ODD-ODD NUCLEI
RESONANCE
SPECTROSCOPY
STABLE ISOTOPES
SYNTHESIS
550200* - Biochemistry
400102 - Chemical & Spectral Procedures