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Titolo:
Kinetic resolution of (+/-)-1-phenylbutan-1-ol by means of CALB-catalyzed aminolyses: A study on the role of the amine in the alcohol resolution
Autore:
Garcia-Urdiales, E; Rebolledo, F; Gotor, V;
Indirizzi:
Univ Oviedo, Dept Quim Organ & Inorgan, E-33006 Oviedo, Spain Univ OviedoOviedo Spain E-33006 Organ & Inorgan, E-33006 Oviedo, Spain
Titolo Testata:
ADVANCED SYNTHESIS & CATALYSIS
fascicolo: 6-7, volume: 343, anno: 2001,
pagine: 646 - 654
SICI:
1615-4150(200108)343:6-7<646:KRO(BM>2.0.ZU;2-V
Fonte:
ISI
Lingua:
ENG
Soggetto:
ANTARCTICA LIPASE-B; ACYL-TRANSFER-REACTIONS; CANDIDA-ANTARCTICA; QUANTITATIVE-ANALYSES; PEPTIDE-SYNTHESIS; ORGANIC-SOLVENTS; ENZYME MEMORY; VINYL ESTERS; TRANSESTERIFICATION; ENANTIOMERS;
Keywords:
alcohols; amines; chiral resolution, enantioselectivity; enzyme catalysis;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
35
Recensione:
Indirizzi per estratti:
Indirizzo: Gotor, V Univ Oviedo, Dept Quim Organ & Inorgan, Julian Claveria 8, E-33006 Oviedo,Spain Univ Oviedo Julian Claveria 8 Oviedo Spain E-33006 Oviedo,Spain
Citazione:
E. Garcia-Urdiales et al., "Kinetic resolution of (+/-)-1-phenylbutan-1-ol by means of CALB-catalyzed aminolyses: A study on the role of the amine in the alcohol resolution", ADV SYNTH C, 343(6-7), 2001, pp. 646-654

Abstract

The kinetic resolution of (+/-)-1-phenylbutan-1-ol [(+/-)-1] by means of CALB-catalyzed aminolysis of its acetyl derivative [(+/-)-2] using (+/-)-1-phenylethanamine [(+/-)-3] as nucleophile is a slower but more enantioselective process (E = 50) than the corresponding CALB-catalyzed transesterification of (+/-)-1 with vinyl acetate (E = 19). The use of triethylamine and acetanilide as additives in the transesterification of (+/-)-1 enhanced the enantiomeric ratio (E = 43 and 38, respectively), thus showing that both thebasic character of the amine as well as its structural nature could be responsible for the enantioselectivity differences observed between the transesterification and aminolysis reactions. We have also carried out the aminolysis of (+/-)-2 using different chiral and non-chiral amines. Enantiomeric ratio values varied significantly with the amine employed, but the enzyme always remained more selective towards the R-enantiomer of the substrate. Among all the amines tested, (+/-)-1-phenylpropan-1-amine [(+/-)-5] was the nucleophile or choice. Analysis or the conversion values for each enantiomeror (+/-)-2 showed that the Selectivity differences exhibited by the lipasein the aminolysis reactions were due to the different stabilization of thefast-reacting enantiomer of the Substrate [(R)-2] during the catalytic process. The CALB behavior in these reactions could be explained on the basis of substrate imprinting effects, which were corroborated by means or enzymerecycling experiments. Finally, a solvent screening allowed the kinetic resolution or this alcohol for synthetic purposes.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 18/01/20 alle ore 21:38:45