INVESTIGADORES
BISOGNO Fabricio Roman
artículos
Título:
Access to Enantiopure a-Alkyl-b-hydroxy Esters through Dynamic Kinetic Resolutions Employing Purified-Overexpressed Alcohol Dehydrogenases
Autor/es:
ANÍBAL CUETOS; ANA RIOZ-MARTÍNEZ; FABRICIO R. BISOGNO; BARBARA GRISCHEK; IVÁN LAVANDERA; GONZALO DE GONZALO; WOLFGANG KROUTIL; VICENTE GOTOR
Revista:
ADVANCED SYNTHESIS & CATALYSIS (PRINT)
Editorial:
WILEY-V C H VERLAG GMBH
Referencias:
Lugar: Weinheim; Año: 2012 vol. 354 p. 1743 - 1749
ISSN:
1615-4150
Resumen:
a-Alkyl-b-hydroxy esters were obtained via dynamic kinetic resolution
(DKR) employing purified or crude E. coli overexpressed alcohol
dehydrogenases (ADHs). ADH-A from R. ruber, CPADH from C. parapsilosis
and TesADH from T. ethanolicus afforded syn-(2R,3S) derivatives with
very high selectivities for sterically not impeded ketones
(small-bulky substrates), while ADHs from S. yanoikuyae (SyADH) and
Ralstonia sp. (RasADH) could also accept bulkier keto esters
(bulky-bulky substrates). SyADH also provided preferentially syn-
(2R,3S) isomers and RasADH showed in some cases good selectivity
towards the formation of anti- (2S,3S) derivatives. With anti-Prelog
ADHs such as LBADH from L. brevis or LKADH from L. kefir, syn-(2S,3R)
alcohols were obtained with high conversions and diastereomeric excess
in some cases, especially with LBADH. Furthermore, due to the
thermodynamically favoured reduction of these substrates, it was
possible to employ just a minimal excess of 2-propanol to obtain the
final products with quantitative conversions.