Unit of Biotechnology, Division of Biological and Life Sciences, Graduate School of Integrated Sciences for Life, Hiroshima University, Higashi-Hiroshima, Hiroshima, Japan.
Hiroshima Research Center for Healthy Aging (HiHA), Hiroshima University, Higashi-Hiroshima, Hiroshima, Japan.
Biosci Biotechnol Biochem. 2022 Jan 24;86(2):177-184. doi: 10.1093/bbb/zbab206.
Streptomyces antibiotic regulatory proteins (SARPs) are well characterized as transcriptional activators for secondary metabolites in Streptomyces species. Streptomyces rochei 7434AN4 harbors 15 SARP genes, among which 3 were located on a giant linear plasmid pSLA2-L and others were on the chromosome. Some SARP genes were cloned into an integrative thiostrepton-inducible vector pIJ8600, and their recombinants were cultivated. The recombinant of SARP gene, SRO_3163, accumulated a UV-active compound YM3163-A, which was not detected in the parent strain and other SARP recombinants. Its molecular formula was established to be C8H11NO. Extensive NMR analysis revealed that YM3163-A is a novel enamide, 2-(cyclohex-2-en-1-ylidene)acetamide, and its structure was confirmed by chemical synthesis including Horner-Wadsworth-Emmons reaction and ammonolysis.
链霉菌抗生素调控蛋白 (SARPs) 作为链霉菌属中次级代谢产物的转录激活因子已得到充分研究。链霉菌罗氏 7434AN4 含有 15 个 SARP 基因，其中 3 个位于一个巨大的线性质粒 pSLA2-L 上，而其他基因则位于染色体上。一些 SARP 基因被克隆到一个整合性硫链丝菌素诱导型载体 pIJ8600 中，并对其重组子进行了培养。SARP 基因 SRO_3163 的重组子积累了一种 UV 活性化合物 YM3163-A，而在亲本菌株和其他 SARP 重组子中未检测到该化合物。其分子式被确定为 C8H11NO。广泛的 NMR 分析表明，YM3163-A 是一种新型的烯酰胺，2-(环己-2-烯-1-亚基)乙酰胺，其结构通过包括 Horner-Wadsworth-Emmons 反应和氨解在内的化学合成得到了证实。
