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五氯化磷辅助下氨基酸的自组装成肽反应研究
引用本文:卢奎,刘艳$D周宁,陈益,冯玉萍,郭祥峰$D陈玮,屈凌波,赵玉芬.五氯化磷辅助下氨基酸的自组装成肽反应研究[J].化学学报,2002,60(2):372-376.
作者姓名:卢奎  刘艳$D周宁  陈益  冯玉萍  郭祥峰$D陈玮  屈凌波  赵玉芬
作者单位:[1]清华大学生命科学与工程研究院化学系生命有机磷化学教育部重点实验室,北京100084 [2]郑州大学化学系,郑州450052
基金项目:国家自然科学基金 (No .39870 415 )资助项目
摘    要: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
修稿时间:2001年6月19日

Studies on the self-assembly of amino acids into peptides mediated by phosphorus pentachloride
LU,Kui a,b LIU,Yan c ZHOU,Ning d CHEN,Yi a FENG,Yu-Ping a GUO,Xiang-Feng a CHEN,Wei d QU,Ling-Bo c ZHAO,Yu-Fen,a,c,d.Studies on the self-assembly of amino acids into peptides mediated by phosphorus pentachloride[J].Acta Chimica Sinica,2002,60(2):372-376.
Authors:LU  Kui a  b LIU  Yan c ZHOU  Ning d CHEN  Yi a FENG  Yu-Ping a GUO  Xiang-Feng a CHEN  Wei d QU  Ling-Bo c ZHAO  Yu-Fen  a  c  d
Institution: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)
Abstract: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.
Keywords:amino acids  phosphorus pentachloride  self-assembly  peptide  ESI mass spectrometry
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