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Chemical synthesis of poly‐γ‐glutamic acid by polycondensation of γ‐glutamic acid dimer: Synthesis and reaction of poly‐γ‐glutamic acid methyl ester
Authors:Fumio Sanda  Taizo Fujiyama  Takeshi Endo
Abstract:α‐Methyl glutamic acid (L ‐L )‐, (L ‐D )‐, (D ‐L )‐, and (D ‐D )‐γ‐dimers were synthesized from L ‐ and D ‐glutamic acids, and the obtained dimers were subjected to polycondensation with 1‐(3‐dimethylaminopropyl)‐3‐ethylcarbodiimide hydrochloride and 1‐hydroxybenzotriazole hydrate as condensation reagents. Poly‐γ‐glutamic acid (γ‐PGA) methyl ester with the number‐average molecular weights of 5000∼20,000 were obtained by polycondensation in N,N‐dimethylformamide in 44∼91% yields. The polycondensation of (L ‐L )‐ and (D ‐D )‐dimers afforded the polymers with much larger |α]D | compared with the corresponding dimers. The polymer could be transformed into γ‐PGA by alkaline hydrolysis or transesterification into α‐benzyl ester followed by hydrogenation. © 2001 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 39: 732–741, 2001
Keywords:α  ‐methyl glutamic acid γ  ‐dimer  polycondensation  poly‐γ  ‐glutamic acid methyl ester  alkaline hydrolysis  transesterification  hydrogenation  poly‐γ  ‐glutamic acid
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