BioChem - DOS

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

Advanced synthesis & catalysis

L'enfant, Mé lanie; Bruna, Felipe; Lorilliè re, Marion; Ocal, Nazim; Fessner, Wolf‐ Dieter; Pollegioni, Loredano; Charmantray, Franck; Hecquet, Laurence

<P><B>Abstract</B></P><P>We described an efficient <I>in situ</I> generation of hydroxypyruvate from <SMALL>d</SMALL>&#8208;serine catalyzed by a <SMALL>d</SMALL>&#8208;amino acid oxidase from <I>Rhodotorula gracilis</I>. This strategy revealed an interesting alternative to the conventional chemical synthesis of hydroxypyruvate starting from toxic bromopyruvate or to the enzymatic transamination from <SMALL>l</SMALL>&#8208;serine requiring an additional substrate as amino acceptor. Hydroxypyruvate thus produced was used as donor substrate of transketolases from <I>Escherichia coli</I> or from <I>Geobacillus stearothermophilus</I> catalyzing the stereoselective formation of a carbon&minus;carbon bond. The enzymatic cascade reaction was performed in one&#8208;pot in the presence of <SMALL>d</SMALL>&#8208;serine and appropriate aldehydes for the synthesis of valuable (3<I>S</I>)&#8208;hydroxyketones, which were obtained with high enantio&#8208; and diastereoselectivity and in good yield. The efficiency of the process was based on the irreversibility of both reactions allowing complete conversion of <SMALL>d</SMALL>&#8208;serine and aldehydes.</P>

2019

1615-4150

1615-4169

361

11

pp.2550-2558

10.1002/adsc.201900109

http://click.ndsl.kr/servlet/OpenAPIDetailView?keyValue=05787966&target=NART&cn=NART97255669

biocatalysis; transketolase; d-amino acid oxidase; hydroxypyruvate; ketoses; stereoselectivity