Citation: Zhong Zhou CHEN, Bo TAN, Yan Mei LI, Yu Fen ZHAO. Theoretical Study on the Activity of α-COOH and β-COOH of N-Phosphoryl Aspartic Acids[J]. Chinese Chemical Letters, ;2001, 12(12): 1093-1096. shu

Theoretical Study on the Activity of α-COOH and β-COOH of N-Phosphoryl Aspartic Acids

Key Laboratory for Bioorganic Phosphorus Chemistry of Education Ministry, Department of Chemistry, School of Life Science and Engineering, Tsinghua University, Beijing 100084

Received Date: 23 April 2001

Fund Project: The authors would like to thank the financial supports from the National Natural Science Foundation of China (No.29802006), the Teaching and Research Award Program for Outstanding Young Teachers in Higher Education Institutions of MOE, P.R.C. and Tsinghua University.

The bio-mimic reactions of N-phosphoryl amino acids are very important in the study of many biochemical processes. The difference of reactivity between α-COOH and β-COOH in phosphoryl aspartic acid was studied by theoretical study (Hartree-Fock and Density Functional methods) in this paper. The intermediates II containing five-membered ring were more stable than III with six-membered ring. While for intermediates III, the isomers with six-membered ring in apical-equatorial spanning arrangement were more stable than those with di-equatorial spanning arrangement. At B3LYP/6-31G^** level, it was shown that transition states IV and V involving α-COOH or β-COOH group had energy barriers of ΔE=58.67 kJ·mol^-1 and 103.94 kJ·mol^-1, respectively. These results were in agreement with the experimental data. So the α-COOH group was involved in form of the intramolecular penta-coordinate phosphoric-carboxylic mixed anhydride intermediates, but not β-COOH group.
- α-Carboxylic group,
- β-carboxylic group,
- theoretical study,
- N-phosphorylation
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