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

Abstract:

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.

SEEK ID: https://fairdomhub.org/publications/417

DOI: 10.1002/adsc.201900109

Projects: TRALAMINOL

Publication type: Not specified

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

Citation: https://onlinelibrary.wiley.com/doi/full/10.1002/adsc.201900109

Date Published: 6th Jun 2019

Registered Mode: Not specified

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Citation
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. https://doi.org/10.1002/adsc.201900109
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Created: 8th Jul 2019 at 16:20

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