CHEMOENZYMATIC SYNTHESIS OF POLY[(2R,3S)- BENZYL BETA-3-METHYLMALATE]- BETA-METHYLASPARTASE AS A VERSATILE ENZYME IN THE PREPARATION OF THE CHIRAL PRECURSOR

Citation
Mm. Bear et al., CHEMOENZYMATIC SYNTHESIS OF POLY[(2R,3S)- BENZYL BETA-3-METHYLMALATE]- BETA-METHYLASPARTASE AS A VERSATILE ENZYME IN THE PREPARATION OF THE CHIRAL PRECURSOR, Comptes rendus de l'Academie des sciences. Serie II. Mecanique, physique, chimie, astronomie, 325(3), 1997, pp. 165-172
Citations number
14
Categorie Soggetti
Multidisciplinary Sciences
ISSN journal
12518069
Volume
325
Issue
3
Year of publication
1997
Pages
165 - 172
Database
ISI
SICI code
1251-8069(1997)325:3<165:CSOPBB>2.0.ZU;2-C
Abstract
beta-methylaspartase from Clostridium tetanomorphum was used under unu sual conditions to produce a mixture of natural (2S,3S) and of uncommo n (2S,3R)-3-methylaspartic acid in a 60:40 mol/mol ratio. Both diaster eoisomers were separated during the mutiple-steps synthesis of the lac tone. The new optically active (3R,4R)-3-methylmalolaclonate of benzyl was obtained with a very high diastereoisomeric excess (> 98%), as de termined by chiral gas chromatography, and polymerized by anionic ring -opening polymerization. Poly[(2R,3S)-benzyl beta-3-methylmalate] was semicrystalline (T-m = 130 degrees C) and highly isotactic according t o the C-13 NMR spectrum. Comparison was made with the poly[2S,3S]-ster eoisomer.