Stereochemical Effect of the Amino Acid Side Chain on the Formation of Penta-coordinate Phosphorus Intermediates from N-Phosphorylamino acid: A Theoretical Study

Acta Chimica Sinica ›› 2006, Vol. 64 ›› Issue (9): 959-962. Previous Articles

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N-磷酰化氨基酸生成五配位磷中间体过程中氨基酸侧链立体化学效应的理论研究

赵丽娇¹，钟儒刚*^,1,2，甄岩¹，赵玉芬²

(¹北京工业大学生命科学与生物工程学院北京 100022)
(²生命有机磷化学及化学生物学教育部重点实验室清华大学化学系北京 100084)

投稿日期:2005-11-08 修回日期:2006-01-13 发布日期:2006-05-15
通讯作者: 钟儒刚

Stereochemical Effect of the Amino Acid Side Chain on the Formation of Penta-coordinate Phosphorus Intermediates from N-Phosphorylamino acid: A Theoretical Study

ZHAO Li-Jiao¹, ZHONG Ru-Gang*^,1,2, ZHEN Yan¹, ZHAO Yu-Fen²

(¹ College of Life Science and Bioengineering, Beijing University of Technology, Beijing 100022)
(² Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology, Ministry of Education,
Department of Chemistry, Tsinghua University, Beijing 100084)

Received:2005-11-08 Revised:2006-01-13 Published:2006-05-15
Contact: ZHONG Ru-Gang

Abstract

The stereochemical effect of the chiral amino acid residues on the formation of penta-coordinate phosphorus intermolecular mixed carboxylic-phosphoric anhydride (IMCPA) from N-phosphorylamino- acids is studied with density functional theory (DFT) calculations at B3LYP/6-311G(d,p) level. The reaction pathways for the formation of penta-coordinate phosphorus intermediates with different configurations through the carboxyl oxygen on amino acid group attacking the phosphoryl group from different directions are simulated and the stereoselectivity in the formation of IMCPA is discussed.

Key words: N-phosphorylamino acid, origin of life, stereochemical effect, DFT

Cite this article

ZHAO Li-Jiao, ZHONG Ru-Gang*^,1,2, ZHEN Yan, ZHAO Yu-Fen². Stereochemical Effect of the Amino Acid Side Chain on the Formation of Penta-coordinate Phosphorus Intermediates from N-Phosphorylamino acid: A Theoretical Study[J]. Acta Chimica Sinica, 2006, 64(9): 959-962.

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N-磷酰化氨基酸生成五配位磷中间体过程中氨基酸侧链立体化学效应的理论研究

Stereochemical Effect of the Amino Acid Side Chain on the Formation of Penta-coordinate Phosphorus Intermediates from N-Phosphorylamino acid: A Theoretical Study

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