Deciphering molecular interaction of binaphthyl compounds with Penicillium expansum lipase: enantioselectivity and reactivity prediction for lipase†,Molecular Systems Design & Engineering

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Deciphering molecular interaction of binaphthyl compounds with Penicillium expansum lipase: enantioselectivity and reactivity prediction for lipase†
Molecular Systems Design & Engineering ( IF 3.2 ) Pub Date : 2018-03-23 00:00:00 , DOI: 10.1039/c7me00120g
Yan Liu _{1,

2,

3,

4,

5} , Longguang Jiang _{4,

5,

6,

7} , Ling Song _{3,

4,

5,

8} , Datao Tu _{1,

2,

3,

4,

5} , Wei Zheng _{1,

2,

3,

4,

5} , Ping Huang _{1,

2,

3,

4,

5} , Mingmao Chen _{4,

5,

7,

9} , Xueyuan Chen _{1,

2,

3,

4,

5}

Affiliation

The determination of the dominant factor for the enantioselectivity and reactivity of lipase-catalyzed reactions of binaphthyl compounds is of wide concern. To understand the stereo-dependent behavior of 2,2-binaphthyl compounds towards lipase, we established a platform for effectively evaluating the reactivity and enantioselectivity of lipase towards binaphthyl compounds by investigating the binding interactions between substrate and lipase. Penicillium expansum lipase (PEL) and three 2-amino-2′-hydroxy-1,1′-binaphthyl compounds (NBs) with different linker lengths were selected as the model lipase and substrates, respectively, in this study. The key interaction parameters such as binding affinities, binding modes, and thermodynamic parameters between NBs and PEL were determined for the first time, and the results revealed that the substrate–lipase binding interaction is a prerequisite for successful lipase-catalyzed reaction. The effect of binding discrepancies of NBs with different alkyl chain lengths on lipase reactivity and enantioselectivity was also unveiled. From the analytical results of NB–PEL binding interactions, a PEL-catalyzed two-step resolution strategy was further established and optimized for the gram-scale synthesis of optically pure NB. The investigation on the molecular interaction between NBs and PEL showed great promise for rationally guiding the synthesis of binaphthyl derivatives that are suitable for efficient optical resolution by the commercially available lipase.

中文翻译：

解密用联萘化合物的分子间相互作用扩展青霉脂肪酶：脂肪酶对映选择性和反应性预测†

确定联萘化合物的脂肪酶催化反应的对映选择性和反应性的主要因素是引起广泛关注的问题。为了了解2,2-联萘化合物对脂肪酶的立体依赖性，我们通过研究底物和脂肪酶之间的结合相互作用，建立了一个有效评估脂肪酶对联萘化合物的反应性和对映选择性的平台。扩展青霉在本研究中，分别选择脂肪酶（PEL）和三种具有不同接头长度的2-氨基-2'-羟基-1,1'-联萘化合物（NBs）作为模型脂肪酶和底物。首次确定了关键亲和力参数，如结合亲和力，结合模式以及NB与PEL之间的热力学参数，结果表明底物-脂肪酶结合相互作用是成功进行脂肪酶催化反应的前提。还揭示了具有不同烷基链长度的NB的结合差异对脂肪酶反应性和对映选择性的影响。根据NB-PEL结合相互作用的分析结果，进一步建立了PEL催化的两步拆分策略，并优化了光学纯NB的克级合成。

更新日期：2018-03-23

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