O-二异丙氧磷酰基丝氨酸(或苏氨酸或酪氨酸)的合成

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

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 。

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.