Qj. Yan et al., REACTIONS OF N-PHOSPHORYL SERINE AND THRE ONINE AND THEIR ESTERS CATALYZED BY IMIDAZOLE, Gaodeng xuexiao huaxue xuebao, 16(10), 1995, pp. 1563-1566
N-phosphoryl amino acids could be catalyzed by imidazole to result in
solvolysis such as ester exchanges on phosphorus, esterification, form
ation of peptides and N-->O migration of the phosphoryl group. For ser
ine and threonine, a phosphaoxazole product was also detected. Only N-
phosphoryl serine and threonine methyl esters were catalyzed by imidaz
ole, A new type of pentacoordinate phosphorus intermediate was propose
d.