Issue 2, 2017

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

Abstract

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-α-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.

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

Supplementary files

Article information

Article type
Paper
Submitted
22 sep 2016
Accepted
18 nov 2016
First published
18 nov 2016

Green Chem., 2017,19, 519-526

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

V. de Berardinis, C. Guérard-Hélaine, E. Darii, K. Bastard, V. Hélaine, A. Mariage, J. Petit, N. Poupard, I. Sánchez-Moreno, M. Stam, T. Gefflaut, M. Salanoubat and M. Lemaire, Green Chem., 2017, 19, 519 DOI: 10.1039/C6GC02652D

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements