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