化学学报 ›› 2002, Vol. 60 ›› Issue (2): 372-376. 上一篇    下一篇

研究论文

五氯化磷辅助下氨基酸的自组装成肽反应研究

卢奎;刘艳$D周宁;陈益;冯玉萍;郭祥峰$D陈玮;屈凌波;赵玉芬   

  1. 清华大学生命科学与工程研究院.北京(100084);清华大学化学系.北京(100084) ;清华大学生命有机磷化学教育部重点实验室.北京(100084);郑州工程学院化学 化工系;郑州大学化学系.郑州(450052)
  • 发布日期:2002-02-15

Studies on the self-assembly of amino acids into peptides mediated by phosphorus pentachloride

Lu Kui;Liu Yan$DZhou Ning;Chen Yi;Feng Yuping;Guo Xiangfeng$DChen Wei;Qu Lingbo;Zhao Yufen   

  1. Qinghua Univ.,, Ctr Wave Scattering & Remote S.Beijing(100084);Tsing Hua Univ, Dept Chem.Beijing(100084);Qinghua Univ.,, Ctr Wave Scattering & Remote S.Beijing(100084);Zhengzhou Univ, Dept Chem. Zhengzhou(450052)
  • Published:2002-02-15

L-α-氨基酸和D-α-氨基酸可与五氯化磷直接发生磷酰化反应,随后自组装成多肽,但β-氨基酸不能成肽,DL-α-氨基酸成肽困难;在SOCl2存在下,α-氨基酸也不能成肽,用电喷雾质谱研究了氨基酸的自组装反应,反应过程中有五元环状的氨基酸五配位磷中间体生成,使用硅烷基保护的氨基酸,在^31PNMR中可观察到五配位磷中间体。

关键词: 五氯化磷, 质谱法, 氯化磷, 氨基酸, 自组装, 多肽, 有机磷化合物, 磷31核磁共振谱法

L-α-Amino acids and D-α-amino acids, mediated by phosphorus pentachloride, could take place the phosphorylation and then assembled itno polypeptides. However, β-amino acids could not assemble into polypeptides, and the self-assembly of DL-α-amino acids into peptides were difficult. α-Amino acids could not assemble into peptides mediated by thionyl chloride. The self-assembly reactions were studied by positive ion electrospray ionization mass spectrometry, and the five-membered cyclic penta-coordinated phosphoryl amino acid intermediates were found in the course of self- assembly into peptides. The intermediates could be trapped by ^31P NMR spectroscopy after amino acids were trimethylsilylized to N, O-bis (trimethylsilyl) amino acids.

Key words: PHOSPHORIC CHLORIDE, MASS SPECTROGRAPHY, PHOSPHORUS CHLORIDE, AMINO ACID, POLYPEPTIDE, ORGANO PHOSPHORUS COMPOUNDS, PHOSPHORUS 31 MAGNETIC RESONANCE SPECTROMETRY

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