Biosynthesis of chiral cyclic and heterocyclic alcohols via CO/C–H/C–O asymmetric reactions
Biosynthesis of chiral cyclic and heterocyclic alcohols via CO/C–H/C–O asymmetric reactions
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DOI：
10.1039/d1cy00113b
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发表时间：
2021-04
影响因子：
5
通讯作者：
L. Qin;Lunjie Wu;Y. Nie;Yan Xu
中科院分区：
文献类型：
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作者：
L. Qin;Lunjie Wu;Y. Nie;Yan Xu
手性环状和杂环醇是精细化学品、农用化学品和手性药物如拉多司替吉、依布鲁维卡和舒洛培南的重要结构单元。天然酶对环上具有大体积取代基或类似大小取代基的分子表现出低亲和力。因此，工程酶代表了手性环状和杂环醇生物合成的替代选择。本文综述了近年来生物催化合成对映体纯的环状和杂环醇的研究进展，包括酶催化CO键的不对称还原、C-H键的不对称羟基化和C-O键的不对称水解反应。本文综述了手性环状和杂环醇的有机合成的理论和实验线索。
Chiral cyclic and heterocyclic alcohols are important structural units for fine chemicals, agrochemicals, and chiral pharmaceuticals such as ladostigil, imbruvica, and sulopenem. Natural enzymes show low affinity toward molecules harboring bulky substituents or similarly-sized substituents on the ring. Thus, engineered enzymes represent an alternative option for the biosynthesis of chiral cyclic and heterocyclic alcohols. This review covers the recent progress in various biological approaches applied to the synthesis of enantiomerically pure cyclic and heterocyclic alcohols, including enzymatic asymmetric reduction of the CO bond, asymmetric hydroxylation of the C–H bond, and asymmetric hydrolysis reaction of the C–O bond. This review gathers relevant theoretical and experimental clues for organic synthesis of chiral cyclic and heterocyclic alcohols.