Studies on the biosynthesis of the antibiotic reductiomycin in Streptomyces xanthochromogenus

Journal Article · Tue Dec 28 23:00:00 EST 1993 · Journal of the American Chemical Society; (United States)

DOI:https://doi.org/10.1021/ja00079a009· OSTI ID:5136198

Cho, H; Beale, J M; Floss, H G ^[1]; Graff, C; Mocek, U ^[2]; Nakagawa, Akira; Omura, Satoshi ^[3]

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1. Univ. of Washington, Seattle, WA (United States) Ohio State Univ., Columbus, OH (United States)
2. Univ. of Washington, Seattle, WA (United States)
3. 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), Journal Name: Journal of the American Chemical Society; (United States) Vol. 115:26; ISSN JACSAT; ISSN 0002-7863
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400102 -- Chemical & Spectral Procedures
550200* -- Biochemistry
59 BASIC BIOLOGICAL SCIENCES
ANTI-INFECTIVE AGENTS
ANTIBIOTICS
BACTERIA
BIOCONVERSION
BIOSYNTHESIS
CATALYSIS
DATA
DEUTERIUM
DRUGS
EXPERIMENTAL DATA
FERMENTATION
HYDROGEN ISOTOPES
INFORMATION
ISOTOPES
LABELLED COMPOUNDS
LIGHT NUCLEI
MAGNETIC RESONANCE
MASS SPECTROSCOPY
MICROORGANISMS
NUCLEAR MAGNETIC RESONANCE
NUCLEI
NUMERICAL DATA
ODD-ODD NUCLEI
RESONANCE
SPECTROSCOPY
STABLE ISOTOPES
STREPTOMYCES
SYNTHESIS