The reaction of cyclo-triphosphate with L-.ALPHA.- or .BETA.-alanine.

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概要

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• The reaction of sodium <I>cyclo</I>-triphosphate(P<SUB>3m</SUB>) with L-α- or β-alanine in an aqueous solution was investigated using anion-exchange chromatography, <SUP>31</SUP>P-NMR spectroscopy, chemical analysis for phosphorus and alanine, IR spectroscopy, and thin-layer chromatography(TLC). 1) P<SUB>3m</SUB> readily reacted with L-α-alanine at pH 10 and 12 to form two orthophosphate derivatives of α-alanine: <I>N</I>-(1-carboxyethyl)phosphoramidate(P<SUB>1</SUB>-(<I>N</I>)ala) and 1,3,2-oxazaphospholidin-2-olate derivative(P<SUB>1</SUB>-(<I>N</I>,<I>O</I>)ala) of five-membered ring structure. 2) Only triphosphate derivative, <I>N</I>-(2-carboxyethyl)triphosphoramidate(P<SUB>3</SUB>-(<I>N</I>)ala), was obtained in the reaction of P<SUB>3m</SUB> and β-alanine. 3) The total yield of P<SUB>1</SUB>-(<I>N</I>)ala and P<SUB>1</SUB>-(<I>N</I>,<I>O</I>)ala was about 75% when P<SUB>3m</SUB> was allowed to react with α-alanine at a molar ratio of 1:3 and pH 12, while the yield of P<SUB>3</SUB>-(<I>N</I>)ala was about 80% in the reaction of P<SUB>3m</SUB> with β-alanine at a molar ratio of 1:1 and pH 12. 4) Oligopeptides suchs as L-alanylalanine(dimer) and L-alanylalanylalanine(trimer) were formed in the reaction of P<SUB>3m</SUB> with α-alanine. 5) Under acidic conditions, P<SUB>3</SUB>-(<I>N</I>)ala recyclized to the starting material P<SUB>3m</SUB> and β-alanine. 6) The mechanism of the reaction of P<SUB>3m</SUB> with α- or β-alanine is discussed.

• 公益社団法人 日本化学会の論文

著者

• TSUHAKO Mitsutomo

  Kobe Pharmaceutical University

• NARIAI Hiroyuki

  Department of Chemical Science and Engineering, Faculty of Engineering, Kobe University

• MOTOOKA Itaru

  Department of Chemical Science and Engineering, Faculty of Engineering, Kobe University

• MIYAJIMA Tohru

  Department of Chemistry and Applied Chemistry, Faculty of Science and Engineering, Saga University

• Ohashi Shigeru

  Department of Chemistry Faculty of Science Kanazawa University

• Nakajima Akemi

  Kobe Women's College of Pharmacy

• Miyajima Tohru

  Department of Chemistry, Faculty of Science

• Ohashi Shigeru

  Department of Chemistry, Faculty of Science

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