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烯二炔聚酮合酶在烯二炔核心生物合成中立体选择性地将β-酮酰基中间体还原为β-D-羟酰基中间体。

Enediyne polyketide synthases stereoselectively reduce the β-ketoacyl intermediates to β-D-hydroxyacyl intermediates in enediyne core biosynthesis.

机构信息

Department of Chemistry, ‡Department of Molecular Therapeutics, and §Natural Products Library Initiatives, The Scripps Research Institute , Jupiter, Florida 33458, United States.

出版信息

Org Lett. 2014 Aug 1;16(15):3958-61. doi: 10.1021/ol501767v. Epub 2014 Jul 14.

DOI:10.1021/ol501767v
PMID:25019332
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4144755/
Abstract

PKSE biosynthesizes an enediyne core precursor from decarboxylative condensation of eight malonyl-CoAs. The KR domain of PKSE is responsible for iterative β-ketoreduction in each round of polyketide chain elongation. KRs from selected PKSEs were investigated in vitro with β-ketoacyl-SNACs as substrate mimics. Each of the KRs reduced the β-ketoacyl-SNACs stereoselectively, all affording the corresponding β-D-hydroxyacyl-SNACs, and the catalytic efficiencies (k(cat)/K(M)) of the KRs increased significantly as the chain length of the β-ketoacyl-SNAC substrate increases.

摘要

PKSE 通过八分子丙二酰辅酶 A 的脱羧缩合生物合成烯二炔核心前体。PKSE 的 KR 结构域负责在每一轮聚酮链延伸中进行迭代的β-酮还原。用β-酮酰基-SNAC 作为底物类似物对选定的 PKSEs 的 KR 进行了体外研究。每个 KR 都对β-酮酰基-SNAC 进行立体选择性还原，均得到相应的β-D-羟基酰基-SNAC，并且随着β-酮酰基-SNAC 底物链长的增加，KR 的催化效率（kcat/KM）显著提高。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e86e/4144755/5dae91280725/ol-2014-01767v_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e86e/4144755/7430bbb0703a/ol-2014-01767v_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e86e/4144755/5dae91280725/ol-2014-01767v_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e86e/4144755/7430bbb0703a/ol-2014-01767v_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e86e/4144755/5dae91280725/ol-2014-01767v_0003.jpg

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Structural and stereochemical analysis of a modular polyketide synthase ketoreductase domain required for the generation of a cis-alkene.生成顺式烯烃所需的模块化聚酮合酶酮还原酶结构域的结构和立体化学分析。
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Cloning and sequencing of the kedarcidin biosynthetic gene cluster from Streptoalloteichus sp. ATCC 53650 revealing new insights into biosynthesis of the enediyne family of antitumor antibiotics.
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