N Imamura, K Kakinuma, N Ikekawa, H Tanaka, S Omura
{"title":"Biosynthesis of vineomycins A1 and B2.","authors":"N Imamura, K Kakinuma, N Ikekawa, H Tanaka, S Omura","doi":"10.7164/antibiotics.35.602","DOIUrl":null,"url":null,"abstract":"<p><p>Biosynthetic studies of the antibacterial and antitumor antibiotics vineomycins A1 (1) and B2 (2), produced by Streptomyces matensis subsp. vineus, were carried out by labeling experiments with [1-13C]- and [1,2-18C2]sodium acetate followed by 18C NMR spectroscopy. The results show that the benz[a]anthraquinone chromophore of 1 is derived from a decacetate metabolite with decarboxylation at the carboxyl end and that 2 is formed via C-C bond cleavage of 1. Isolation of rabelomycin from the fermentation broth of the same strain suggests a close biosynthetic relationship among the simple benz[a]anthraquinone antibiotics such as rabelomycin, tetrangomycin, aquayamycin, a C-glycosylated benz[a]anthraquinone, and vineomycins. These biosynthetic data prompted us to reconsider the previously published structure of the antibiotic SS-228Y, which has not been revised.</p>","PeriodicalId":501839,"journal":{"name":"The Journal of Antibiotics","volume":" ","pages":"602-8"},"PeriodicalIF":0.0000,"publicationDate":"1982-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.7164/antibiotics.35.602","citationCount":"55","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"The Journal of Antibiotics","FirstCategoryId":"3","ListUrlMain":"https://doi.org/10.7164/antibiotics.35.602","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 55
Abstract
Biosynthetic studies of the antibacterial and antitumor antibiotics vineomycins A1 (1) and B2 (2), produced by Streptomyces matensis subsp. vineus, were carried out by labeling experiments with [1-13C]- and [1,2-18C2]sodium acetate followed by 18C NMR spectroscopy. The results show that the benz[a]anthraquinone chromophore of 1 is derived from a decacetate metabolite with decarboxylation at the carboxyl end and that 2 is formed via C-C bond cleavage of 1. Isolation of rabelomycin from the fermentation broth of the same strain suggests a close biosynthetic relationship among the simple benz[a]anthraquinone antibiotics such as rabelomycin, tetrangomycin, aquayamycin, a C-glycosylated benz[a]anthraquinone, and vineomycins. These biosynthetic data prompted us to reconsider the previously published structure of the antibiotic SS-228Y, which has not been revised.