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化学学报
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化学学报 ›› 2001, Vol. 59 ›› Issue (10): 1660-1666. 上一篇    下一篇

研究论文

手性膦肽核酸单体的合成

武芸;徐杰诚   

  1. 中国科学院上海有机化学研究所.上海(200032);中国科学院生命有机化学国家 重点实验室
  • 发布日期:2001-10-15

Synthesis of chiral phosphono-peptide nucleic acid monomers

Wu Yun;Xu Jiecheng   

  1. Shanghai Inst Organ Chem., CAS.Shanghai(200032)
  • Published:2001-10-15

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肽核酸是一种潜在的反义和反基因药物。膦肽结构的引入克服了肽核酸低水溶性和低细胞膜通透性等缺点，有利于肽核酸的应用。本研究报道手性磷肽核酸单体的合成。还原氨化方法被用于实现N-Boc,N-Fmoc保护的丙氨醛与甘氨膦酸二酯的偶联，BBC-Cl,FEP等缩合剂被用于实现碱基侧链和母链的高效缩合。

关键词: 核酸, 膦肽核酸, 还原, 氨化, 缩合, 反基因药物

Peptide nucleic acids are the potential candiated of antisense and anitgene. Chiral monomer backbones were efficiently prepared by reductive amination of N-Boc or N-Fmoc protected L alaninal with aminomethylphosphate diethyl ester and subsequent acylation of free secondary amines with thymine-1-ylacetic acid. After chemical swith of N-Boc to N-Fmoc, protected chiral phosphono-PNA monomers were obtained.

Key words: NUCLEIC ACIDS, REDUCTION, AMMONIATION, CONDENSATION

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