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有机化学
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有机化学 ›› 2005, Vol. 25 ›› Issue (06): 712-715. 上一篇    下一篇

研究论文

赖氨酸衍生氮杂大环化合物的固相合成

杨潇骁，邱传亮，王德心*   

  1. (中国医学科学院药物研究所 北京 100050)
  • 收稿日期:2004-06-25 修回日期:2004-01-04 发布日期:2005-05-30
  • 通讯作者: 王德心

Solid-phase Synthesis of Aza-macrocyclic Compounds Derived from Lysine Residues

YANG Xiao-Xiao, QIU Chuan-Liang, WANG De-Xin*   

  1. (Institute of Materia Medica, Chinese Academy of Medical Science, Beijing 100050)
  • Received:2004-06-25 Revised:2004-01-04 Published:2005-05-30
  • Contact: WANG De-Xin

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1418

被引次数

14

基于固相载体的假稀释效应, 设计并合成了由赖氨酸为前体结构衍生的氮杂大环化合物8, 9, 10, 12及13. 合成中的关键构件是在固相树脂上肽链的N端键合的二个相邻的赖氨酸残基, 并以溴乙酸为桥连组份, 先后经酰化及亲核取代(SN2)反应完成三氮杂十六元环骨架的构建. 5种粗产物的总收率在68.9%～86.1%之间, 并全部经氨基酸组成分析及ESI-MS分析表征.

关键词: 氮杂大环, 固相合成, 肽结构改造

Triaza-macrocyclic compounds, based on the pseudo-dilution effect on solid support, were designed and synthesized. The key building blocks for cyclization were two lysine residues and bromoacetic acid as the bridging components via acylation-SN2 reaction in sequence. By present procedure, five target compounds 8, 9, 10, 12 and 13 with trinitrogen atoms in a 16-membered ring were obtained in good overall yields of 68.9%～86.1% and characterized by amino acid analysis and ESI-MS.

Key words: nitrogen containing macro-ring, peptide structure modification, solid-phase synthesis