STUDIES ON THE BIOSYNTHESIS OF THE ANTIBIOTIC REDUCTIOMYCIN IN STREPTOMYCES-XANTHOCHROMOGENUS
STUDIES ON THE BIOSYNTHESIS OF THE ANTIBIOTIC REDUCTIOMYCIN IN STREPTOMYCES-XANTHOCHROMOGENUS
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DOI：
10.1021/ja00079a009
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发表时间：
1993-12-29
影响因子：
15
通讯作者：
FLOSS, HG
中科院分区：
文献类型：
--
作者：
CHO, H;BEALE, JM;FLOSS, HG
The biosynthesis of the antibiotic reductiomycin (1) in Streptomyces xanthochromogenus was investigated by feeding experiments with radioactive and stable isotope-labeled precursors. NMR and mass spectroscopic analyses of the labeled 1 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-C-13]benzoic acid and 4-hydroxy-[7-C-13]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.
