34a-Hydroxylation in Rifamycin Biosynthesis Catalyzed by Cytochrome P450 Encoded by rif-orf13

doi:10.6023/cjoc201811018

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (4): 1169-1174.DOI: 10.6023/cjoc201811018 Previous Articles Next Articles

Notes

Rif-orf13编码的细胞色素P450催化利福霉素生物合成过程中C34a位的羟化反应

周强^a,b, 罗光彩^b, 张惠展^a, 唐功利^b

a 华东理工大学生物工程学院上海 200030;
b 中国科学院上海有机化学研究所上海 200032

收稿日期:2018-11-12 修回日期:2018-12-06 发布日期:2018-12-17
通讯作者: 张惠展, 唐功利 E-mail:gltang@sioc.ac.cn;huizhzh@ecust.edu.cn

34a-Hydroxylation in Rifamycin Biosynthesis Catalyzed by Cytochrome P450 Encoded by rif-orf13

Zhou Qiangm^a,b, Luo Guang-Cai^b, Zhang Huizhan^a, Tang Gong-Li^b

a Department of Applied Biology, East China University of Science and Technology, Shanghai 200030;
b State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received:2018-11-12 Revised:2018-12-06 Published:2018-12-17
Contact: 10.6023/cjoc201811018 E-mail:gltang@sioc.ac.cn;huizhzh@ecust.edu.cn

1. 34a-Hydroxylation in Rifamycin Biosynthesis Catalyzed by Cytochrome P450 Encoded by rif-orf13.PDF(1143KB)

Abstract

The biosynthetic pathway of rifamycins is still not completely deciphered after decades of study. For example, the gene responsible for the oxidative elimination of C34a is not identified. It was proposed that some cytochrome P450 is related to this essential biosynthetic step in the modification of rifamycin. Here, cytochrome P450 encoding genes rif-orf0, 4 and 13 from rifamycin biosynthetic gene cluster were heterologously expressed in Streptomyces lividans and fed with 16-demethyl-34a-deoxyrifamycin W (1). Compound 1 was completely converted into 16-demethylrifamycin W (2) in the strain harboring rif-orf13. His₆-tagged Orf13 was prepared from E. coli BL21 (DE3) and characterized to be active cytochrome P450. Enzymatic assays demonstrated that compound 1 could be converted into 2 by Orf13 as in vivo. Therefore, we concluded that rif-orf13 is responsible for the hydroxylation on C34a in the biosynthesis of rifamycins. In addition, it's role in vivo could be functionally complemented by rif-orf5, which encoding another cytochrome P450 enzyme.

Key words: cytochrome P450, hydroxylation, rifamycin, rif-orf13

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Zhou Qiangm, Luo Guang-Cai, Zhang Huizhan, Tang Gong-Li. 34a-Hydroxylation in Rifamycin Biosynthesis Catalyzed by Cytochrome P450 Encoded by rif-orf13[J]. Chin. J. Org. Chem., 2019, 39(4): 1169-1174.

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Rif-orf13编码的细胞色素P450催化利福霉素生物合成过程中C34a位的羟化反应

34a-Hydroxylation in Rifamycin Biosynthesis Catalyzed by Cytochrome P450 Encoded by rif-orf13

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