Polyketide Ring Expansion Mediated by a Thioesterase, Chain Elongation and Cyclization Domain, in Azinomycin Biosynthesis: Characterization of AziB and AziG

Mori Shogo; Simkhada Dinesh; Zhang Huitu; Erb Megan S.; Zhang Yang; Williams Howard; Fedoseyenko Dmytro; Russell William K.; Kim Doyong; Fleer Nathan; Ealick Steven E.; Watanabe Coran M. H.

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Polyketide Ring Expansion Mediated by a Thioesterase, Chain Elongation and Cyclization Domain, in Azinomycin Biosynthesis: Characterization of AziB and AziG

机译：在阿奇霉素生物合成中由硫酯酶，链延伸和环化域介导的聚酮化合物环的扩展：AziB和AziG的表征

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The azinomycins are a family of potent antitumor agents with the ability to form interstrand cross-links with DNA. This study reports on the unusual biosynthetic formation of the 5-methyl naphthoate moiety, which is essential for effective DNA association. While sequence analysis predicts that the polyketide synthase (AziB) catalyzes the formation of this naphthoate, 2-methylbenzoic acid, a truncated single-ring product, is formed instead. We demonstrate that the thioesterase (AziG) acts as a chain elongation and cyclization (CEC) domain and is required for the additional two rounds of chain extension to form the expected product.

机译：阿奇霉素是一类有效的抗肿瘤药物，具有与DNA形成链间交联的能力。该研究报道了5-甲基萘甲酸部分的异常生物合成形成，这对于有效的DNA缔合至关重要。虽然序列分析预测聚酮化合物合酶（AziB）催化这种萘甲酸酯的形成，但形成了截短的单环产物2-甲基苯甲酸。我们证明，硫酯酶（AziG）充当链延长和环化（CEC）域，并且需要另外两轮扩链才能形成预期的产品。

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《Biochemistry》 |2016年第4期|共11页
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Mori Shogo; Simkhada Dinesh; Zhang Huitu; Erb Megan S.; Zhang Yang; Williams Howard; Fedoseyenko Dmytro; Russell William K.; Kim Doyong; Fleer Nathan; Ealick Steven E.; Watanabe Coran M. H.;
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1. Polyketide Ring Expansion Mediated by a Thioesterase, Chain Elongation and Cyclization Domain, in Azinomycin Biosynthesis: Characterization of AziB and AziG [J] . Mori Shogo, Simkhada Dinesh, Zhang Huitu, Biochemistry . 2016,第4期

机译：在阿奇霉素生物合成中由硫酯酶，链延伸和环化域介导的聚酮化合物环的扩展：AziB和AziG的表征
2. Structure and function of an iterative polyketide synthase thioesterase domain catalyzing Claisen cyclization in aflatoxin biosynthesis [J] . Tyler Paz Korman, Jason M. Crawford, Jason W. Labonte, Proceedings of the National Academy of Sciences of the United States of America . 2010,第14期

机译：黄曲霉毒素生物合成中催化克莱森环化的迭代聚酮化合物合酶硫酯酶结构域的结构和功能
3. Thioesterase Domains of Fungal Nonreducing Polyketide Synthases Act as Decision Gates during Combinatorial Biosynthesis [J] . Yuquan Xu, Tong Zhou, Shuwei Zhang, Journal of the American Chemical Society . 2013,第29期

机译：真菌非还原性聚酮化合物合酶的硫酯酶结构域在组合生物合成过程中充当决策门
4. Carboxylic acid-mediated, epoxide-initiated cation-olefin cyclizations and "A-ring" formation in sterol biosynthesis. [D] . Staas, Donnette Daley. 1998

机译：固醇生物合成中羧酸介导的环氧化物引发的阳离子-烯烃环化和“ A环”形成。
5. Polyketide Ring Expansion Mediated by a Thioesterase CEC Domain in Azinomycin Biosynthesis: Characterization of AziB and AziG [O] . Shogo Mori, Dinesh Simkhada, Huitu Zhang, -1

机译：硫酯酶CEC域在阿奇霉素生物合成中介导的聚酮化合物环的扩展：AziB和AziG的表征。
6. Polyketide Ring Expansion Mediated by a Thioesterase, Chain Elongation and Cyclization Domain, in Azinomycin Biosynthesis: Characterization of AziB and AziG [O] . Shogo Mori, Dinesh Simkhada, Huitu Zhang, 2016

机译：聚酮环膨胀由硫代酯酶，链伸长率和环化结构域介导的硫代霉素生物合成：αzib和azig的表征

Polyketide Ring Expansion Mediated by a Thioesterase, Chain Elongation and Cyclization Domain, in Azinomycin Biosynthesis: Characterization of AziB and AziG

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