Stereoselectivity in biocatalytic enantioconvergent reactions and a computer program for its determination
2002; Elsevier BV; Volume: 13; Issue: 4 Linguagem: Inglês
10.1016/s0957-4166(02)00084-8
ISSN1362-511X
Autores Tópico(s)Carbohydrate Chemistry and Synthesis
ResumoFor the description of the stereoselectivity of (bio)catalytic asymmetric reactions which may proceed via different regio- or stereo-isomeric pathways (e.g. catalysed by epoxide hydrolases, dehalogenases, sulfatases or glycosidases), a parameter ‘RI’ (Retention–Inversion ratio) was introduced in analogy to the Enantiomeric Ratio (E), which describes enantioselectivity. A computer program was developed for the treatment of the kinetics of such single-step processes, which offer the potential of deracemization, i.e. a single stereoisomeric product is formed from a racemate in an enantioconvergent fashion. By analysis of experimentally determined progress curves of the enantiomeric excess of substrate and product (e.e.S, e.e.P, respectively) and the conversion (c), relative first-order rate constants ki, the enantioselectivity (E) and the RI ratio (RI) can be determined; in addition, processes can be simulated based on assumed ki values.
Referência(s)