Synthesis of (R)-Mellein by a partially reducing iterative polyketide synthase
Mellein and the related 3,4-dihydroisocoumarins are a family of natural products with interesting biological properties. The mechanisms of dihydroisocoumarin biosynthesis remain largely speculative today. Here we report the synthesis of mellein by a partially reducing iterative polyketide synthase (...
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sg-ntu-dr.10356-976152020-03-07T12:18:06Z Synthesis of (R)-Mellein by a partially reducing iterative polyketide synthase Sun, Huihua Ho, Chun Loong Ding, Feiqing Soehano, Ishin Liu, Xue-Wei Liang, Zhao-Xun School of Biological Sciences DRNTU::Science::Biological sciences Mellein and the related 3,4-dihydroisocoumarins are a family of natural products with interesting biological properties. The mechanisms of dihydroisocoumarin biosynthesis remain largely speculative today. Here we report the synthesis of mellein by a partially reducing iterative polyketide synthase (PR-PKS) as a pentaketide product. Remarkably, despite the head-to-tail homology shared with several fungal and bacterial PR-PKSs, the mellein synthase exhibits a distinct keto reduction pattern in the synthesis of the pentaketide. We present evidence to show that the ketoreductase (KR) domain alone is able to recognize and differentiate the polyketide intermediates, which provides a mechanistic explanation for the programmed keto reduction in these PR-PKSs. 2013-07-11T06:14:38Z 2019-12-06T19:44:37Z 2013-07-11T06:14:38Z 2019-12-06T19:44:37Z 2012 2012 Journal Article https://hdl.handle.net/10356/97615 http://hdl.handle.net/10220/11204 10.1021/ja304905e en Journal of the American chemical society © 2012 American Chemical Society. |
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DRNTU::Science::Biological sciences Sun, Huihua Ho, Chun Loong Ding, Feiqing Soehano, Ishin Liu, Xue-Wei Liang, Zhao-Xun Synthesis of (R)-Mellein by a partially reducing iterative polyketide synthase |
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Mellein and the related 3,4-dihydroisocoumarins are a family of natural products with interesting biological properties. The mechanisms of dihydroisocoumarin biosynthesis remain largely speculative today. Here we report the synthesis of mellein by a partially reducing iterative polyketide synthase (PR-PKS) as a pentaketide product. Remarkably, despite the head-to-tail homology shared with several fungal and bacterial PR-PKSs, the mellein synthase exhibits a distinct keto reduction pattern in the synthesis of the pentaketide. We present evidence to show that the ketoreductase (KR) domain alone is able to recognize and differentiate the polyketide intermediates, which provides a mechanistic explanation for the programmed keto reduction in these PR-PKSs. |
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School of Biological Sciences |
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School of Biological Sciences Sun, Huihua Ho, Chun Loong Ding, Feiqing Soehano, Ishin Liu, Xue-Wei Liang, Zhao-Xun |
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Article |
author |
Sun, Huihua Ho, Chun Loong Ding, Feiqing Soehano, Ishin Liu, Xue-Wei Liang, Zhao-Xun |
author_sort |
Sun, Huihua |
title |
Synthesis of (R)-Mellein by a partially reducing iterative polyketide synthase |
title_short |
Synthesis of (R)-Mellein by a partially reducing iterative polyketide synthase |
title_full |
Synthesis of (R)-Mellein by a partially reducing iterative polyketide synthase |
title_fullStr |
Synthesis of (R)-Mellein by a partially reducing iterative polyketide synthase |
title_full_unstemmed |
Synthesis of (R)-Mellein by a partially reducing iterative polyketide synthase |
title_sort |
synthesis of (r)-mellein by a partially reducing iterative polyketide synthase |
publishDate |
2013 |
url |
https://hdl.handle.net/10356/97615 http://hdl.handle.net/10220/11204 |
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1681046305698217984 |