Microbial hormones in Streptomyces coelicolor A3 (2)

点击翻译按钮获取中文摘要

Streptomycetes are Gram-positive soil bacteria characterized by their ability to produce numerous kinds of useful secondary metabolites as well as by their complex life cycle including the formation of aerial mycelia and spores. The two characteristic phenotypes have been know to link each other, and low-molecular-weight compounds called gamma-butyrolactone autoregulators have been found in some Streptomyces species to regulate the two phenotypes. However, with the most genetically studied among Streptomyces species, Streptomyces coelicolor A3(2), nothing has been know on the nature of the intrinsic hormones to regulate the antibiotic production or morphological differentiation.1. S.coelicolor A3(2) was studied intensively whether it has low-molecular-weight compounds to regulate the antibiotic production or the morphological differentiation.2. S.coelicolor A3(2) was found to have a compound named Scb1 which induces the production of two antibiotics, actinorhodin and undecylprodigiosin.3. From 500-liters culture broth, 320 mug of pure Scb1 was purified.4. Plain structure of Scb1 was estimated from 600 MHz H-NMR and MS analyses.5. Chiral synthetic routes for four possible Scb1 stereoisomers were established, and comparison of natural Scb1 with the four synthetic isomers resulted in the determination of Scb1 as (2R, 3R, 1'R)-2-(1'-hydroxy-6'-methylheptyl)-3-hydroxymethyl gamma-butanolide.