Synthesis of polypeptides from activated urethane derivatives of α‐amino acids |
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| Authors: | Yasutaka Kamei Atsushi Sudo Haruo Nishida Kiyoshi Kikukawa Takeshi Endo |
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| Institution: | 1. Molecular Engineering Institute, Kinki University, 11‐6 Kayanomori, Iizuka, Fukuoka 820‐8555, Japan;2. Department of Polymer Science and Engineering, Faculty of Engineering, Yamagata University, 4‐3‐16 Jonan, Yonezawa, Yamagata 992‐8510, Japan;3. School of Humanity‐Oriented Science and Engineering, Kinki University, 11‐6 Kayanomori, Iizuka, Fukuoka 820‐8555, Japan |
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| Abstract: | A series of activated urethane‐type derivatives of α‐amino acids were synthesized and applied to polypeptide synthesis. The urethane used herein, N‐(4‐nitrophenoxycarbonyl)‐α‐amino acids 1 , were synthesized by N‐carbamoylation of γ‐benzyl‐L ‐glutamate, β‐benzyl‐L ‐aspartate, L ‐leucine, L ‐phenylalanine, and L ‐proline, with 4‐nitrophenyl chloroformate. When 1 was dissolved in N,N‐dimethylacetamide (DMAc) and heated at 60 °C, it was smoothly converted into the corresponding polypeptides with releasing 4‐nitrophenol and carbon dioxide. Spectroscopic analyses of the obtained polypeptides revealed that they were comparable with the authentic polypeptides synthesized by the ring‐opening polymerizations of amino acid N‐carboxyanhydrides (NCAs). Besides the successful polycondensations of a series of 1 , their polycondensations of 1a and other 1 were also successfully carried out to obtain the corresponding statistic copolypeptides. © 2008 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 46: 2525–2535, 2008 |
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| Keywords: | amino acid amino acid N‐carboxyanhydride (NCA) copolymerization peptides polycondensation |
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