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One‐Pot Cascade Synthesis of (3 S )‐Hydroxyketones Catalyzed by Transketolase via Hydroxypyruvate Generated in Situ from d ‐Serine by d ‐Amino Acid Oxidase
Author(s) -
L'enfant Mélanie,
Bruna Felipe,
Lorillière Marion,
Ocal Nazim,
Fessner WolfDieter,
Pollegioni Loredano,
Charmantray Franck,
Hecquet Laurence
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201900109
Subject(s) - chemistry , serine , d amino acid oxidase , transamination , transketolase , substrate (aquarium) , amino acid , catalysis , stereochemistry , enzyme catalysis , enzyme , organic chemistry , oxidase test , biochemistry , biology , ecology
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 (3 S )‐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.