Peme Thabo, Brady Dean, Juma Wanyama, Makatini Maya
Molecular Sciences Institute, School of Chemistry, University of the Witwatersrand Private Bag 3, PO WITS 2050 South Africa
RSC Adv. 2021 Nov 15;11(58):36670-36681. doi: 10.1039/d1ra06616a. eCollection 2021 Nov 10.
This study describes the design and synthesis of mimetic peptides modelled on the catalytic active site of the fructose-1,6-bisphosphate aldolase (FBPA) enzyme. The synthesized peptides consisting of the turn motifs and catalytic site amino acids of FBPA enzyme were evaluated for catalytic activity in direct asymmetric aldol reactions of ketones and aldehydes. The influence of substrate scope, catalyst loading and solvents including water, on the reaction were also investigated. Nuclear magnetic resonance (NMR) and circular dichroism (CD) were used to determine the secondary structure of the peptides to provide an understanding of the structure-activity relationship. The peptides showed catalytic activity and the aldol products were obtained in low yields (up to 44%), but excellent enantioselectivity (up to 93%) and moderate diastereoselectivity (65 : 35).
本研究描述了以果糖-1,6-二磷酸醛缩酶（FBPA）酶的催化活性位点为模型的模拟肽的设计与合成。对由FBPA酶的转角基序和催化位点氨基酸组成的合成肽，在酮与醛的直接不对称羟醛反应中进行催化活性评估。还研究了底物范围、催化剂负载量以及包括水在内的溶剂对反应的影响。利用核磁共振（NMR）和圆二色性（CD）来确定肽的二级结构，以了解结构-活性关系。这些肽表现出催化活性，羟醛产物的产率较低（最高44%），但对映选择性优异（最高93%），非对映选择性适中（65∶35）。
