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学科主题: 生命有机化学
题名: Biosynthesis of 3-methoxy-5-methyl naphthoic acid and its incorporation into the antitumor antibiotic azinomycin B
其他题名: 3-甲氧基-5-甲基耐甲酸的生物合成及其组合入抗肿瘤抗生素阿进霉素B中
作者: Ding W(丁伟) ; Deng W(邓玮) ; Tang MC(唐满成) ; Zhang Q(张琪) ; Tang GL(唐功利) ; Bi YR(毕玉蓉) ; Liu W(刘文)
通讯作者: 刘文
刊名: Mol. Biosyst.
发表日期: 2010
卷: 6, 期:6, 页:1071-1081
收录类别: SCI
部门归属: 兰州大学; 中国科学院上海有机化学研究所
英文摘要: Azinomycin B is a potent antitumor antibiotic that features a set of unusual, densely assembled functionalities. Among them, the 3-methoxy-5-methylnaphthoic acid (NPA) moiety provides an important noncovalent association with DNA, and may, therefore, contribute to the specificity of DNA alkylation for biological activity exhibition. We have previously cloned and sequenced the azinomycin B biosynthetic gene cluster, and proposed that four enzymes: AziB, AziB1, AziB2, and AziA1, are involved in the naphthoate moiety formation and incorporation. In this study, we report in vivo and/or in vitro characterizations of the P450 hydroxylase AziB1, the O-methyltransferase AziB2, and the substrate specificity of the non-ribosomal peptide synthetase (NRPS) AziA1, providing insights into the timing of individual steps in the late-stage modification of 5-methyl-NPA synthesized by the iterative type I polyketide synthase AziB. AziB1 catalyzes a regiospecific hydroxylation at the C3 position of the free naphthoic acid 5-methyl-NPA to produce 3-hydroxy-5-methyl-NPA, and the resulting hydroxyl group is subsequently O-methylated by AziB2 to furnish the methoxy functionality. The di-domain NRPS AziA1 specifically incorporates 3-methoxy-5-methyl-NPA via an unusual A domain to initiate the backbone formation of azinomycin B. AziA1 activates several analogues of the natural starter unit, suggesting a potential for production by metabolic engineering of new azinomycin analogues differing in their NPA moieties.
语种: 英语
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WOS记录号: WOS:000277832900018
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/28461
Appears in Collections:生命有机化学国家重点实验室_期刊论文

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Recommended Citation:
Ding W,Deng W,Tang MC,et al. Biosynthesis of 3-methoxy-5-methyl naphthoic acid and its incorporation into the antitumor antibiotic azinomycin B[J]. Mol. Biosyst.,2010,6(6):1071-1081.
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