One‐Pot Cascade Synthesis of (3S)‐Hydroxyketones Catalyzed by Transketolase via Hydroxypyruvate Generated in Situ from d‐Serine by d‐Amino Acid Oxidase


We described an efficient in situ generation of hydroxypyruvate from d‐serine catalyzed by a d‐amino acid oxidase from Rhodotorula gracilis. This strategy revealed an interesting alternative to the conventional chemical synthesis of hydroxypyruvate starting from toxic bromopyruvate or to the enzymatic transamination from l‐serine requiring an additional substrate as amino acceptor. Hydroxypyruvate thus produced was used as donor substrate of transketolases from Escherichia coli or from Geobacillus stearothermophilus catalyzing the stereoselective formation of a carbon−carbon bond. The enzymatic cascade reaction was performed in one‐pot in the presence of d‐serine and appropriate aldehydes for the synthesis of valuable (3S)‐hydroxyketones, which were obtained with high enantio‐ and diastereoselectivity and in good yield. The efficiency of the process was based on the irreversibility of both reactions allowing complete conversion of d‐serine and aldehydes.


DOI: 10.1002/adsc.201900109


Publication type: Not specified

Journal: Volume361, Issue11 Special Issue: Biocatalysis, Pages 2550-2558


Date Published: 6th Jun 2019

Registered Mode: Not specified

help Submitter
L'enfant, M., Bruna, F., Lorillière, M., Ocal, N., Fessner, W. D., Pollegioni, L., Charmantray, F., & Hecquet, L. (2019). One‐Pot Cascade Synthesis of (3S)‐Hydroxyketones Catalyzed by TransketolaseviaHydroxypyruvate Generatedin Situfromd‐Serine byd‐Amino Acid Oxidase. In Advanced Synthesis & Catalysis. Wiley.

Views: 1331

Created: 8th Jul 2019 at 16:20

help Tags

This item has not yet been tagged.

help Attributions


Powered by
Copyright © 2008 - 2022 The University of Manchester and HITS gGmbH

By continuing to use this site you agree to the use of cookies