Reactions of N-Phosphoryl Serine and Threonine and Their Esters Catalyzed by Imidazole

Chem. J. Chinese Universities ›› 1995, Vol. 16 ›› Issue (10): 1563.

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Reactions of N-Phosphoryl Serine and Threonine and Their Esters Catalyzed by Imidazole

YAN Qing-Jin, YIN Ying-Wu, WANG Qian, MAO Qing-Qun, ZHAO Yu-Fen

Bio-organic Phosphorus Chemistry Laboratory, Department of Chemistry, Tsinghua University, Beijing, 100084

Received:1994-11-08 Revised:1995-02-14 Online:1995-10-24 Published:1995-10-24

Abstract

Abstract: N-phosphoryl amino acids could be catalyzed by imidazole to result in solvolysis such as ester exchanges on phosphorus, esterification, formation of peptides and N→Omigration of the phosphoryl group. For serine and threonine, a phosphaoxazole product was also detected. Only N-phosphoryl serine and threonine methyl esters were catalyzed by imidazole, Anew type of pentacoordinate phosphorus intermediate was proposed.

Key words: Imidazole, Phosphoamino acids, Catalysis, Penta-coordinate phosphorus

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YAN Qing-Jin, YIN Ying-Wu, WANG Qian, MAO Qing-Qun, ZHAO Yu-Fen . Reactions of N-Phosphoryl Serine and Threonine and Their Esters Catalyzed by Imidazole[J]. Chem. J. Chinese Universities, 1995, 16(10): 1563.

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Reactions of N-Phosphoryl Serine and Threonine and Their Esters Catalyzed by Imidazole

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