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Chemoenzymatic One‐Pot Synthesis of Enantiopure L ‐Arylalanines from Arylaldehydes
Author(s) -
Paizs Csaba,
Katona Adrian,
Rétey János
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500902
Subject(s) - enantiopure drug , chemistry , phenylalanine ammonia lyase , wittig reaction , organic chemistry , enantiomeric excess , enantiomer , aryl , ammonia , reagent , esterase , enzyme , enantioselective synthesis , catalysis , alkyl , peroxidase
Various enantiopure L ‐arylalanines can be prepared from the corresponding arylaldehydes in one‐pot fashion by a combination of chemical and enzymatic reactions. The reagents used were (triphenyl‐λ 5 ‐phosphanylidene)ethyl acetate (Wittig reaction), porcine liver esterase (PLE), phenylalanine ammonia lyase (PAL) from parsley and ammonia. As examples the following aryl groups were used: phenyl, 4‐chlorophenyl, 3‐fluorophenyl and thiophen‐2‐yl. The pure L ‐enantiomers of phenyl‐, 4‐chlorophenyl‐, 3‐fluorophenyl‐ and thiophen‐2‐ylalanines were obtained after ion‐exchange chromatography in 88, 78, 72 and 91 % yields, respectively, calculated from the arylaldehydes. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)