Rational design of short-chain dehydrogenase/reductase for enantio-complementary synthesis of chiral 1,2-diols by successive hydroxymethylation and reduction of aldehydes,Biotechnology and Bioengineering

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Rational design of short-chain dehydrogenase/reductase for enantio-complementary synthesis of chiral 1,2-diols by successive hydroxymethylation and reduction of aldehydes
Biotechnology and Bioengineering ( IF 3.5 ) Pub Date : 2024-09-10 , DOI: 10.1002/bit.28841
Xiu-Xin Ren _{1,

2} , Bing-Mei Su _{1,

2} , Xin-Qi Xu _{1,

2} , Lian Xu _{1,

2} , Juan Lin _{1,

2}

Affiliation

Enantiopure 1,2-diols are widely used in the production of pharmaceuticals, cosmetics, and functional materials as essential building blocks or bioactive compounds. Nevertheless, developing a mild, efficient and environmentally friendly biocatalytic route for manufacturing enantiopure 1,2-diols from simple substrate remains a challenge. Here, we designed and realized a step-wise biocatalytic cascade to access chiral 1,2-diols starting from aromatic aldehyde and formaldehyde enabled by a newly mined benzaldehyde lyase from Sphingobium sp. combined with a pair of tailored-made short-chain dehydrogenase/reductase from Pseudomonas monteilii (PmSDR-MuR and PmSDR-MuS) capable of producing (R)- and (S)-1-phenylethane-1,2-diol with 99% ee. The planned biocatalytic cascade could synthesize a series of enantiopure 1,2-diols with a broad scope (16 samples), excellent conversions (94%–99%), and outstanding enantioselectivity (up to 99% ee), making it an effective technique for producing chiral 1,2-diols in a more environmentally friendly and sustainable manner.

中文翻译：

通过连续羟甲基化和醛还原合成手性 1,2-二醇对映体互补的短链脱氢酶/还原酶的合理设计

Enantiopure 1,2-二醇广泛用于药品、化妆品和功能材料的生产，作为基本结构单元或生物活性化合物。然而，开发一种温和、高效且环保的生物催化途径，从简单底物生产对映体纯 1,2-二醇仍然是一个挑战。在这里，我们设计并实现了一个逐步生物催化级联反应，以从芳香醛和甲醛开始获得手性 1,2-二醇，该反应由新开采的鞘氨醇属苯甲醛裂解酶实现。与一对来自蒙特利假单胞菌的定制短链脱氢酶/还原酶（PmSDR-MuR 和 PmSDR-MuS）相结合，能够产生具有 99% ee 的（R）- 和（S）-1-苯乙烷-1,2-二醇。计划中的生物催化级联反应可以合成一系列对映体纯 1,2-二醇，范围广（16 个样品）、出色的转化率（94%–99%）和出色的对映体选择性（高达 99% ee），使其成为以更环保和可持续的方式生产手性 1,2-二醇的有效技术。

更新日期：2024-09-10

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