Fmoc-L-Orn(Boc)-Gly-OH的合成工艺研究  

Study on the Synthetic Process of Fmoc-L-Orn(Boc)-Gly-OH

作　　者：张东海 郑征 杨再宽 吴惠峰 孙梦春 曹力智 周星宇 杨大成 ZHANG Donghai;ZHENG Zheng;YANG Zaikuan;WU Huifeng;SUN Mengchun;CAO Lizhi;ZHOU Xingyu;YANG Dacheng(Chengdu Zybiochemical Technology Co.,Ltd.,Chengdu 611633,China)

机构地区：[1]成都郑源生化科技有限公司,四川成都611633

出　　处：《合成化学》2023年第5期383-388,共6页Chinese Journal of Synthetic Chemistry

基　　金：四川省科技计划重点研发项目(2021YFG0110)。

摘　　要：N^(α)-芴甲氧羰基-N^(δ)-叔丁氧羰基-L-鸟氨酰甘氨酸(Fmoc-L-Orn(Boc)-Gly-OH)是宫缩抑制剂阿托西班的短肽片段,通过液相合成法高效合成高纯度的Fmoc-L-Orn(Boc)-Gly-OH片段可以有效降低阿托西班的合成成本。采用液相合成方法,以N-羟基-5-降冰片烯-2,3-二甲酰亚胺(HONB)活化N^(α)-芴甲氧羰基-N^(δ)-叔丁氧羰基-L-鸟氨酸(Fmoc-L-Orn(Boc)-OH)的羧基高效合成Fmoc-L-Orn(Boc)-Gly-OH,并对反应物料配比和反应溶剂体系进行了研究,得到了最优的Fmoc-L-Orn(Boc)-Gly-OH合成工艺,该工艺操作简单、成本低且产物纯度高,可用于工业化生产。Fmoc-L-Orn(Boc)-Gly-OH is a short peptide fragment of the Atosiban which is a contraction inhibitor.In order to effectively reduce the preparation cost of atosiban,an efficient liquid phase synthesis of Fmoc-L-Orn(Boc)-Gly-OH with high-purity was really needed.In this paper,a facile method which can prepare high-purity Fmoc-L-Orn(Boc)-Gly-OH by activating the carboxyl group of Fmoc-L-Orn(Boc)-OH by HONB/DIC and following a condensation with H-Gly-OH was reported.The optimum synthetic process of Fmoc-L-Orn(Boc)-Gly-OH which has the advantages of simple operation,low cost,high product purity and can be used industrially was obtained by studying the reaction condition.

关 键 词：阿托西班 Fmoc-L-Orn(Boc)-Gly-OH 多肽片段 合成工艺 液相合成 

分 类 号：O622.6[理学—有机化学]