Formation of Dipeptide in the Reaction of Amino Acids with cyclo-Triphosphate

概要

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The reaction of glycine (Gly) or L-α-alanine (Ala) with inorganic sodium cyclo-triphosphate hexahydrate (P_<3m>), Na_3P_3O_9・6H_2O gave dipeptides and the phosphorylated products of amino acids, but the reaction of L-valine (Val) or L-serine (Ser) with P_<3m> showed no peptide formation. The phosphorylated products of these reactions have a P-N bond in their molecules. Gly reacted with P_<3m> to give N-(carboxymethyl)phosphoramidate (P_1(N)Gly : 1a), 5-oxo-1,3,2-oxazaphospholidin-2-olate 2-oxide (P_1(N, O)Gly : 2a), which was a five-membered cyclic anhydride, N-(N-phosphonoglycyl)glycine (P_1-N(GlyGly) : 3a), N-(carboxymethyl)triphosphoramidate (P_3(N)Gly : 4a), and glycyl-glycine (GlyGly). A five-membered cyclic anhydride (2a) which was formed via an intramolecular cyclization of 4a was found to be a key intermediate for the production of GlyGly. Phosphorylation of Ala with P_<3m> also gave alanylalanine (AlaAla) in addition to the phosphorylated products including a five-membered cyclic anhydride. The yields of GlyGly and AlaAla were 15.8 and 2.0%, respectively. In the reactions of Val and Ser with P_<3m>, only N-(1-carboxy-2-methylpropyl)phosphoramidate (P_1-(N)Val : 1c) and N-(1-carboxy-2-hydroxyethyl)phosphoramidate (P_1-(N)Ser : 1d) were formed and their dipeptides were not obtained at all. The mechanism of the dipeptide formation will be discussed.
公益社団法人日本薬学会の論文
1993-11-15