Construction of a Highly Diastereoselective Aldol Reaction System with l-Threonine Aldolase by Computer-Assisted Rational Molecular Modification and Medium Engineering.,Organic Letters

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Construction of a Highly Diastereoselective Aldol Reaction System with l-Threonine Aldolase by Computer-Assisted Rational Molecular Modification and Medium Engineering.
Organic Letters ( IF 4.9 ) Pub Date : 2020-07-27 , DOI: 10.1021/acs.orglett.0c01792
Wenlong Zheng ₁ , Kaitong Chen ₁ , Zhe Wang ₂ , Xiuli Cheng ₂ , Gang Xu ₁ , Lirong Yang _{1,

3} , Jianping Wu _{1,

3}

Affiliation

Diastereoselectivity of l-threonine aldolase (LTA) was determined by paths of aldehydes attacking a pyridoxal phosphate–glycine complex. Thus, strategies of enhancing the syn path and blocking the anti path were performed to modify LTA. A mutant (Y31H/N305R) was constructed with a substrate preference increase from 3.32 to 42.04. Medium engineering was investigated. Consequently, the de value of l-syn-3-[4-(methylsulfonyl)phenylserine] reached 93.1% (87.2%_conv). The study clarified the factors affecting diastereoselectivity of LTA and provided a theorem for rational modification of LTA’s diastereoselectivity.

中文翻译：

通过计算机辅助合理分子修饰和介质工程构建具有 l-苏氨酸醛缩酶的高度非对映选择性醛醇反应系统。

非对映选择性的升-苏氨酸醛缩酶（LTA）是由醛攻击一个磷酸吡哆醛-甘氨酸络合物的路径来确定。因此，执行增强同步路径和阻止反路径的策略来修改 LTA。构建了一个突变体 (Y31H/N305R)，底物偏好从 3.32 增加到 42.04。研究了介质工程。因此，l - syn- 3-[4-(甲基磺酰基)苯基丝氨酸]的de值达到93.1% (87.2% _conv )。该研究阐明了影响LTA非对映选择性的因素，为合理修改LTA的非对映选择性提供了定理。

更新日期：2020-08-08

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