SYNTHESIS OF N-PHOSPHOPEPTIDES COUPLED BY DICHLOROTRIPHENYLPHOSPHORANE

Abstract

Coupling of N-phosphoamino acids 2 and amino acid methyl esters by dichlorotriphenylphosphorane 3 produced N-phosphopeptide methyl esters 5, which were sequentially hydrolyzed in triethylamine or dilute NaOH aqueous solution. The target products N-phosphodipeptides 6 were obtained in reasonable yields and high purity after isolation using extraction method. The convenient and efficient approach could be generally used for synthesis of polypeptides.

ACKNOWLEDGMENTS

The authors would like to thank the financial supports from the Chinese National Natural Science Foundation (No. 29902003), the Ministry of Science and Technology, the Chinese Education Ministry and Tsinghua University.