HOMOCHIRAL ORGANOELEMENT ANALOGS OF NATURAL COMPOUNDS .2. 3-AMINO-4,4,4-TRIFLUOROBUTANOIC ACID - SYNTHESIS, ENZYMATIC RESOLUTION AND DETERMINATION OF ABSOLUTE-CONFIGURATIONS OF ENANTIOMERS

Authors
KUKHAR VP SOLOSHONOK VA SVEDAS VK KOTIK NV GALAEV IY KIRILENKO AG KOZLOVA EV
Citation
Vp. Kukhar et al., HOMOCHIRAL ORGANOELEMENT ANALOGS OF NATURAL COMPOUNDS .2. 3-AMINO-4,4,4-TRIFLUOROBUTANOIC ACID - SYNTHESIS, ENZYMATIC RESOLUTION AND DETERMINATION OF ABSOLUTE-CONFIGURATIONS OF ENANTIOMERS, Bioorganiceskaa himia, 19(4), 1993, pp. 474-477
Citations number
5
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Bioorganiceskaa himia → ACNP
ISSN journal
01323423
Volume
19
Issue
4
Year of publication
1993
Pages
474 - 477
Database
ISI
SICI code
0132-3423(1993)19:4<474:HOAONC>2.0.ZU;2-6
Abstract
Racemic 3-amino-4,4.4-trifluorobutanoic acid was synthesized by conden sation of 4,4,4-trifluoroacetoacetic acid methyl ester with benzylamin e, isomerisation of the enamine to 3-(N-benzyliden)amino-4,4,4-trifluo robutanoic acid and hydrolysis of the Schiff base. The racemic amino a cid was resolved via the penicillin acylase catalyzed hydrolysis of it s phenylacetyl derivative, and the absolute configuration of the (-)-e nantiomer was determined by X-ray analysis. [alpha]D25 for (R)- and (S )-3-amino-4,4,4-trifluorobutanoic acid (1%, 6 N HCl) are +27.6 and -27 .2-degrees, respectively.