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有机化学
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有机化学 ›› 2004, Vol. 24 ›› Issue (6): 650-653. 上一篇    下一篇

研究论文

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

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介绍一种简单方便地合成O-二异丙氧磷酰基丝氨酸(或苏氨酸或酪氨酸)的方法.其中O-二异丙氧磷酰基-L-丝氨酸(或苏氨酸)可从对应的N-磷酰化-L-丝氨酸(或苏氨酸)利用磷酰基N→O迁移的性质并在超声辅助下合成,而N-二异丙氧磷酰基-L-丝氨酸(或苏氨酸)的合成由L-丝氨酸(或苏氨酸)在次氯酸钠的水溶液中高收率地获得.O-二异丙氧磷酰基酪氨酸的合成可通过铜盐同时保护氨基和羧基,使用二异丙基磷酰氯为磷酰化试剂磷酰化,用硫化氢脱铜保护制备.

关键词: 丝氨酸, 苏氨酸, 酪氨酸, 磷酰化, 合成

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