Chinese Journal of Organic Chemistry ›› 2004, Vol. 24 ›› Issue (6): 650-653. Previous Articles     Next Articles

O-二异丙氧磷酰基丝氨酸(或苏氨酸或酪氨酸)的合成

张建臣a, 曹书霞a, 陈晓岚a, 陈黎a, 赵玉芬*,a,b   

  1. a郑州大学化学系化学生物学重点实验室 郑州 450052
    b清华大学生命有机磷化学与化学生物学教育部重点实验室 北京 100084
  • 收稿日期:2003-09-04 修回日期:2003-12-13 接受日期:2003-12-29 发布日期:2022-09-21
  • 通讯作者: *E-mail: zicb@zzu.edu.cn
  • 基金资助:
    国家自然科学基金(No. 20132020)资助项目.

A Novel Synthesis of O-Phosphorylated Amino Acids Containing Hydroxy SideChain Group

ZHANG, Jian-Chena, CAO, Shu-Xiaa, CHEN, Xiao-Lana, CHEN, Lia, ZHAO, Yu-Fen*,a,b   

  1. a The Key Laboratory of Chemical Biology, Department of Chemistry, ZhengzhouUniversity, Zhengzhou 450052
    b The Key Laboratory for Bioorganic Phosphorus Chemistry and Chemical Biologyof Ministry of Education, Tsinghua University, Beijing 100084
  • Received:2003-09-04 Revised:2003-12-13 Accepted:2003-12-29 Published:2022-09-21

In this article, O-diisoproppyloxyphosphoryl-L-serine, -threonine and -tyrosine were designed and synthesized. Among them, O-diisopropyloxyphosphoryl-L-serine or -threonine was obtained by the migration of phosphoryl group from nitrogen to oxygen of the corresponding N-diisopropyloxyphosphoryl-L-serine or -threonine under ultrasonic irradiation. N-Diisoproppyloxyphosphoryl-L-serine or -threonine was successfully prepared from diisopropyl phosphite and serine or threonine in sodium hypochlorite aqueous media in good yield. O-Diisopropyloxyphosphoryl-L-tyrosine was synthesized via reaction of L-tyrosine cupric complex with diisopropyl phosphorochloridate, then unprotection by sulfide hydrogen.

Key words: serine, threonine, tyrosine, phosphorylation, synthesis