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Alkali-catalyzed ring closure of pyruvoylglycine

, : Alkali-catalyzed ring closure of pyruvoylglycine. Archives of Biochemistry and Biophysics 31(1): 83-89

The product of the treatment of pyruvoylglycine with alkali at 25[degree] was isolated in crystalline form. The compound may exist either as the monohydrate or in the anhydrous form. The empirical composition of the anhydrous product is identical with that of pyruvoylglycine, it possesses a pK' of 3.8 and forms a monosodium salt. On destructive distillation with lime, products giving characteristic pyrrole reactions are formed. The absorption spectra in the u.-v. and in the infrared resemble those of pyrrolidone carboxylic acid, and on hydrolysis in 5 N HCl close to 1 mole of DL-alanine if formed. Pyruvoylglycine under the same conditions yields 1 mole of glycine. It was concluded that the treatment of pyruvoylglycine by alkali under mild conditions leads to an irreversible ring closure and the formation of the isomeric gamma-hydroxy-pyrrolidonecarboxylic acid. This ring closure, leading to the establishment of two centers as asymmetry, would explain in part the origin of the racemic alanine formed on treatment with boiling 5 NHC1.


PMID: 14820341

DOI: 10.1016/0003-9861(51)90186-5

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