Protease-catalyzed regioselective polymerization and copolymerization of glutamic acid diethyl ester.
Protease-catalyzed polymerization and copolymerization of L-glutamic acid diethyl ester hydrochloride (1) have been performed in a buffer of high concentration. Papain and bromelain showed high catalytic activity toward the polymerization. H-H COSY NMR analysis of the product showed the exclusive formation of poly(alpha-peptide), which was further confirmed by comparison with NMR spectra of poly(alpha-methyl gamma-L-glutamate). The papain-catalyzed polymerization of gamma-methyl L-glutamate did not occur under the similar reaction conditions, supporting the regioselective production of the polymer having an alpha-peptide linkage from 1. The effects of the reaction parameters have been systematically investigated. The copolymerization of 1 with various amino acid esters took place by the papain catalyst to give peptide copolymers.
Uyama
Hiroshi
H
Department of Materials Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 606-8501, Japan.
Fukuoka
Tokuma
T
Komatsu
Izuru
I
Watanabe
Takashi
T
Kobayashi
Shiro
S
D000596:Amino Acids / Q000737:chemistry; D001963:Bromelains / Q000737:chemistry; D010450:Endopeptidases / Q000737:chemistry*; D005971:Glutamates / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008956:Models, Chemical; D010206:Papain / Q000737:chemistry; D011099:Polyglutamic Acid / Q000031:analogs & derivatives* / Q000737:chemistry; D011108:Polymers / Q000138:chemical synthesis*
D000596:Amino Acids; D005971:Glutamates; D011108:Polymers; C011829:glutamic acid diethyl ester; C030315:poly-gamma-methylglutamate; D011099:Polyglutamic Acid; D001963:Bromelains; D010450:Endopeptidases; D010206:Papain