Isolation and structural elucidation of tetracenomycin F2 and tetracenomycin F1: early intermediates in the biosynthesis of tetracenomycin C in Streptomyces glaucescens.
This report describes the fermentation, isolation, and structural elucidation of tetracenomycin (Tcm) F2 [2], a metabolite produced by a blocked mutant strain WMH1092 of the Tcm C [1] producer Streptomyces glaucescens and by the recombinant strain S. glaucescens WMH1077 (pWHM722). Elucidation of the Tcm F2 structure shows that 2 is the earliest intermediate identified to date in the biosynthesis of 1. This is supported by the fact that 2 is very efficiently biotransformed to 1 by the S. glaucescens WMH1068 strain and is enzymatically converted to Tcm F1 [3] and to Tcm D3 [4], a known intermediate of Tcm C biosynthesis.
Shen
B
B
School of Pharmacy, University of Wisconsin, Madison 53706.
Nakayama
H
H
Hutchinson
C R
CR
D000873:Anthracenes / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism*; D000900:Anti-Bacterial Agents / Q000096:biosynthesis / Q000737:chemistry* / Q000302:isolation & purification; D003500:Cyclization; D005285:Fermentation; D009682:Magnetic Resonance Spectroscopy; D009154:Mutation; D009279:Naphthacenes / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism*; D011995:Recombination, Genetic; D013302:Streptomyces / Q000737:chemistry / Q000235:genetics / Q000378:metabolism*
D000873:Anthracenes; D000900:Anti-Bacterial Agents; D009279:Naphthacenes; C083904:tetracenomycin F1; C083905:tetracenomycin F2