Synthesis and Properties of High Molecular Weight Polypeptides Containing Proline

High-purity N-carboxy-L-proline anhydride (N-carboxy-2-pyrrolidinecarboxylic acid anhydride) was synthesized. We used triethylamine instead of expensive Ag2O to remove HCl during the synthesis. Copolypeptides with a random sequence of L-proline (Pro) with glycine, L-alanine (Ala), L-α-aminobuthyric...

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Bibliographic Details
Published inBulletin of the Chemical Society of Japan Vol. 66; no. 4; pp. 1269 - 1272
Main Authors Iizuka, Yasuko, Uchida, Chieko, Wakamatsu, Kaori, Oya, Masanao
Format Journal Article
LanguageEnglish
Published Tokyo The Chemical Society of Japan 01.04.1993
Chemical Society of Japan
Subjects
Aminoacid polymers
Applied sciences
Exact sciences and technology
Physicochemistry of polymers
Synthetic biopolymers
Proline polymer
Preparation
Molecular weight
Aminoacid polymer
Solubility
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Summary:High-purity N-carboxy-L-proline anhydride (N-carboxy-2-pyrrolidinecarboxylic acid anhydride) was synthesized. We used triethylamine instead of expensive Ag2O to remove HCl during the synthesis. Copolypeptides with a random sequence of L-proline (Pro) with glycine, L-alanine (Ala), L-α-aminobuthyric acid (Abu), L-Norvaline (Nva) or L-leucine (Leu) were synthesized by copolymerization of the corresponding N-carboxy-α-amino acid anhydrides in solution. Copolypeptides of Pro with Ala or Abu were partially soluble in water. However, the copolypeptides of proline with Nva or Leu with longer side chains were insoluble in water. The conformation of water-soluble copolymer at various pH was analyzed by circular dichroism (CD). The structures of the polypeptides in aqueous solution were almost independent of the pH, and were in a collagen-like conformation.
ISSN:0009-2673
1348-0634
DOI:10.1246/bcsj.66.1269