| Hydrolysis Reaction of N-Phosphoryl-α-, β- and γ-amino Acids Studied by HPLC |
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| 引用本文： | 强黎明,曹书霞,赵晓洋,刘若雨,刘继红,卢建莎,赵玉芬.Hydrolysis Reaction of N-Phosphoryl-α-, β- and γ-amino Acids Studied by HPLC[J].中国化学,2007,25(10):1559-1562. |
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| 作者姓名： | 强黎明 曹书霞 赵晓洋 刘若雨 刘继红 卢建莎 赵玉芬 |
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| 作者单位： | [1]The Key Laboratory of Chemical Biology, Department of Chemistry, Zhengzhou University, Zhengzhou, Henan 450052, China [2]The Key Laboratory for Bioorganic Phosphorus Chemistry and Chemical Biology of the Ministry of Education, Department of Chemistry, School of Life Sciences and Engineering, Tsinghua University, Beijing 100084, China |
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| 基金项目： | Project supported by the National Natural Science Foundation of China （Nos. 20572061, 20672104）. |
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| 摘 要： | The hydrolysis reactions of N-（O,O＇diisopropyl）phosphoryl-L-α-alanine （DIPP-L-α-Ala）, N-（O,O＇diisopropyl）- phosphoryl-D-α-alanine （DIPP-D-α-Ala）, N-（O,O＇-diisopropyl）phosphoryl-β-alanine （DIPP-β-Ala） and N-（O,O＇-diisopropyl）phosphoryl-γ-amino butyric acid （DIPP-γ-Aba）, were studied by HPLC and their hydrolysis reaction kinetic equations were obtained. Under acid conditions, the reaction rate of DIPP-L-α-Ala was close to that of DIPP-D-α-Ala and the same rule was true between DIPP-β-Ala and DIPP-γ-Aba. Meantime, the reaction rate of DIPP-L/D-α-Ala was as 10 times as that of DIPP-β-Ala or DIPP-γ-Aba. Under basic conditions, the hydrolysis reactions of DIPP-β-Ala and DIPP-γ-Aba almost did not take place and the reaction rate of DIPP-L/D-α-Ala was about 1/10 of that under acid conditions. Moreover, theoretical calculation further illuminated the differences of the hydrolysis rate from the view of energy. The results would provide some helpful clues to why nature chose a-amino acids but not other kinds of analogs as protein backbones.
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| 关 键 词： | 高性能液体色谱法 N-磷酰基氨基酸 水解反应 化学反应动力学 |
| 修稿时间： | 2006-12-31 |
Hydrolysis Reaction of N‐Phosphoryl‐α‐, β‐ and γ‐amino Acids Studied by HPLC |
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| QIANG, Li-Ming CAO, Shu-Xia ZHAO, Xiao-Yang LIU, Ruo-Yu LIU, Ji-Hong LU, Jian-Sha ZHAO, Yu-Fen.Hydrolysis Reaction of N‐Phosphoryl‐α‐, β‐ and γ‐amino Acids Studied by HPLC[J].Chinese Journal of Chemistry,2007,25(10):1559-1562. |
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| Authors: | QIANG Li-Ming CAO Shu-Xia ZHAO Xiao-Yang LIU Ruo-Yu LIU Ji-Hong LU Jian-Sha ZHAO Yu-Fen |
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| Institution: | a The Key Laboratory of Chemical Biology, Department of Chemistry, Zhengzhou University, Zhengzhou, Henan 450052, China; b The Key Laboratory for Bioorganic Phosphorus Chemistry and Chemical Biology of the Ministry of Education, Department of Chemistry, School of Life Sciences and Engineering, Tsinghua University, Beijing 100084, China |
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| Abstract: | The hydrolysis reactions of N‐(O,O′‐diisopropyl)phosphoryl‐L‐α‐alanine (DIPP‐L‐α‐Ala), N‐(O,O′‐diisopropyl)‐ phosphoryl‐D‐α‐alanine (DIPP‐D‐α‐Ala), N‐(O,O′‐diisopropyl)phosphoryl‐β‐alanine (DIPP‐β‐Ala) and N‐(O,O′‐ diisopropyl)phosphoryl‐γ‐amino butyric acid (DIPP‐γ‐Aba), were studied by HPLC and their hydrolysis reaction kinetic equations were obtained. Under acid conditions, the reaction rate of DIPP‐L‐α‐Ala was close to that of DIPP‐D‐α‐Ala and the same rule was true between DIPP‐β‐Ala and DIPP‐γ‐Aba. Meantime, the reaction rate of DIPP‐L/D‐α‐Ala was as 10 times as that of DIPP‐β‐Ala or DIPP‐γ‐Aba. Under basic conditions, the hydrolysis reactions of DIPP‐β‐Ala and DIPP‐γ‐Aba almost did not take place and the reaction rate of DIPP‐L/D‐α‐Ala was about 1/10 of that under acid conditions. Moreover, theoretical calculation further illuminated the differences of the hydrolysis rate from the view of energy. The results would provide some helpful clues to why nature chose α‐amino acids but not other kinds of analogs as protein backbones. |
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| Keywords: | N-phosphoryl amino acid hydrolysis reaction kinetics HPLC |
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