Expanding the reaction space of aldolases using hydroxypyruvate as a nucleophilic substrate

被引：28
作者：
de Berardinis, Veronique [1 ,2 ,3 ]
Guerard-Helaine, Christine [4 ,5 ]
Darii, Ekaterina [1 ,2 ,3 ]
Bastard, Karine [1 ,2 ,3 ]
Helaine, Virgil [4 ,5 ]
Mariage, Aline [1 ,2 ,3 ]
Petit, Jean-Louis [1 ,2 ,3 ]
Poupard, Nicolas [4 ,5 ]
Sanchez-Moreno, Israel [4 ,5 ]
Stam, Mark [1 ,2 ,3 ]
Gefflaut, Thierry [4 ,5 ]
Salanoubat, Marcel [1 ,2 ,3 ]
Lemaire, Marielle [4 ,5 ]
机构：
[1] CEA, DRF, Genoscope, IG,UMR 8030, F-91057 Evry, France
[2] CNRS, UMR8030, F-91057 Evry, France
[3] Univ Evry Val Essonne, UMR 8030, F-91057 Evry, France
[4] Univ Blaise Pascal, Clermont Univ, ICCF, BP 10448, F-63000 Clermont Ferrand, France
[5] CNRS, UMR 6296, BP 80026, F-63177 Aubiere, France
来源：
GREEN CHEMISTRY | 2017年 / 19卷 / 02期
关键词：
CLASS-II ALDOLASE; ENZYMATIC-ACTIVITIES; ENOLASE SUPERFAMILY; EVOLUTION; PATHWAY; DISCOVERY; MECHANISM; ENZYMES; SPECIFICITY; DERIVATIVES;
D O I：
10.1039/c6gc02652d
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Aldolases are key biocatalysts for stereoselective C-C bond formation allowing access to polyoxygenated chiral units through direct, efficient, and sustainable synthetic processes. The aldol reaction involving unprotected hydroxypyruvate and an aldehyde offers access to valuable polyhydroxy-alpha-keto acids. However, this undescribed aldolisation is highly challenging, especially regarding stereoselectivity. This reaction was explored using, as biocatalysts, a collection of aldolases selected from biodiversity. Several enzymes that belong to the same pyruvate aldolase Pfam family (PF03328) were found to produce the desired hexulosonic acids from hydroxypyruvate and D-glyceraldehyde with complementary stereoselectivities. One of them was selected for the proof of concept as a biocatalytic tool to prepare five (3S,4S) aldol adducts through an eco-friendly process.
引用
收藏
页码：519 / 526
页数：8
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