Studies of Unnatural Amino Acids and Their Peptides. IV. The Syntheses of DL-β-(5-Cytosinyl)-α-alanine Peptides

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概要

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• DL-β-(5-Cytosinyl)-α-alanine and its dipeptides with glycine were synthesized. The benzyloxycarbonylation of this amino acid afforded the α-<I>N</I>-substituted derivative, but all attempts to obtain the diacylated derivative were unsuccessful. The condensation of the benzyloxycarbonyl derivative with glycine ethyl ester by the carbodiimide method afforded the expected dipeptide, though the yield was low (18%); it was accompanied by a large amount of a bicyclic compound, a lactam produced by an intramolecular acylation. The ethyl ester hydrochloride of this amino acid could not be obtained in a pure state, probably because of its ready cyclization to the same lactam structure under weakly acidic conditions. This complication could be avoided by using the tertiary butyl in place of the ethyl ester. Benzyloxycarbonylglycine <I>p</I>-nitrophenyl ester was condensed smoothly with this ester, affording the expected dipeptide in a 53% yield. The carbodiimide method could also be used, but it was less effective.

• 公益社団法人 日本化学会の論文

著者

• Watanabe Hiroshi

  Laboratory Of Toxicology Central Research Laboratories Of Meiji Seika Kaisha Ltd.

• Kuwata Shigeru

  Laboratory of Chemistry Faculty of Science K\={o}nan University

• Takeuchi Koji

  Laboratory of Chemistry, Faculty of Science, K\={o}nan University

• Shimada Mitsuhisa

  Laboratory of Chemistry, Faculty of Science, K\={o}nan University

• Asai Yoshiya

  Laboratory of Chemistry, Faculty of Science, K\={o}nan University

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