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Synthesis of Polypeptide-Polyether Conjugates from an Activated Urethane Derivative of γ-Benzyl-L-glutamate as a Monomer

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Abstract

N-(4-Nitrophenoxycarbonyl)-γ-benzyl-L-glutamate (1) was heated at 60 °C in N,N-dimethylacetoamide (DMAc) in the presence of p-(tert-butyl)phenylmethylamine (2) to afford poly(γ-benzyl-L-glutamate) in high yield. 1H NMR analysis of the obtained polymer revealed that the p-(tert-butyl)phenylmethyl group was successfully introduced into the polymer chain end. Under the same conditions, polycondensations of 1 in the presence of poly(ethylene glycol)s having amino terminals were performed. Both of the components were consumed quantitatively to afford the corresponding block copolymers having poly(γ-benzyl-L-glutamate) and poly(ethylene glycol) segments. The molecular weights of the copolymers were controlled by the feed ratio [1]0/[amino group in the macroinitiator]0.

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Authors and Affiliations

  1. Molecular Engineering Institute, Kinki University, 11-6 Kayanomori, Iizuka, 820-8555, Fukuoka, Japan

    Yasutaka Kamei, Atsushi Sudo, Haruo Nishida, Takeshi Endo & Takeshi Endo

  2. Department of Polymer Science and Engineering, Faculty of Engineering, Yamagata University, 4-3-16 Jonan, Yonezawa, 992-8510, Yamagata, Japan

    Yasutaka Kamei

  3. School of Humanity-Oriented Science and Engineering, Kinki University, 11-6 Kayanomori, Iizuka, 820-8555, Fukuoka, Japan

    Yasutaka Kamei & Kiyoshi Kikukawa

Authors
  1. Yasutaka Kamei
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  2. Atsushi Sudo
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  3. Haruo Nishida
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  4. Kiyoshi Kikukawa
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  5. Takeshi Endo
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Kamei, Y., Sudo, A., Nishida, H. et al. Synthesis of Polypeptide-Polyether Conjugates from an Activated Urethane Derivative of γ-Benzyl-L-glutamate as a Monomer . Polym. Bull. 60, 625–634 (2008). https://doi.org/10.1007/s00289-008-0900-3

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  • DOI: https://doi.org/10.1007/s00289-008-0900-3

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