Ab initio studies on structures of the hexa-coordinate phosphorus intermediate for the phosphoryl ester exchange and N → O migration reactions of dimethyloxyphosphoryl-threonine

Chang Guo Zhan; Suehiro Iwata

doi:10.1016/S0009-2614(95)01254-0

Ab initio studies on structures of the hexa-coordinate phosphorus intermediate for the phosphoryl ester exchange and N → O migration reactions of dimethyloxyphosphoryl-threonine

Chang Guo Zhan, Suehiro Iwata

Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

7 Scopus citations

Abstract

Recently observed unusual chemical reactivities of the N-phosphoryl amino acids reveal a special hexa-coordinate phosphorus intermediate may exist in the reaction process. It looks unstable and has not been observed directly. We report results obtained from ab initio studies of dimethyloxyphosphoryl-threonine and the corresponding hexa-coordinate phosphorus intermediate. The calculated results show that the hexa-coordinate phosphorous intermediate is a stable structure and all the PO and PN bonds in the intermediate should be much more active. From the calculated results, it is very easy to understand the observed reactivities of dimethyloxyphosphoryl-threonine and other similar dialkyloxyphosphoryl amino acids.

Original language	English
Pages (from-to)	401-407
Number of pages	7
Journal	Chemical Physics Letters
Volume	247
Issue number	4-6
DOIs	https://doi.org/10.1016/S0009-2614(95)01254-0
State	Published - Dec 29 1995

Bibliographical note

Funding Information:
This project was partially supported by Grant-in-Aids for Scientific Research (No. 04243102) and for Priority Area (04640458) of the Ministry of Education, Science and Culture of Japan, and by the Excellent University Teacher's Foundation of the State Education Commission of China. One of the authors (CGZ) wishes to thank the Japan Society for Promotion of Science for providing financial support (JSPS RONPAKU Fellow program) to his stay at the Institute for Molecular Science and to thank Professor Y.F. Zhao for introducing their interesting experimental results to him.

Funding

This project was partially supported by Grant-in-Aids for Scientific Research (No. 04243102) and for Priority Area (04640458) of the Ministry of Education, Science and Culture of Japan, and by the Excellent University Teacher's Foundation of the State Education Commission of China. One of the authors (CGZ) wishes to thank the Japan Society for Promotion of Science for providing financial support (JSPS RONPAKU Fellow program) to his stay at the Institute for Molecular Science and to thank Professor Y.F. Zhao for introducing their interesting experimental results to him.

Funders	Funder number
Program for New Century Excellent Talents in University
Excellent Young University Teacher’s Foundation of the State Education Commission of China
Japan Society for the Promotion of Science
Ministry of Education, Culture, Sports, Science and Technology

ASJC Scopus subject areas

General Physics and Astronomy
Physical and Theoretical Chemistry

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@article{a4f78ccffa574e05b97f7fb6bc06b825,

title = "Ab initio studies on structures of the hexa-coordinate phosphorus intermediate for the phosphoryl ester exchange and N → O migration reactions of dimethyloxyphosphoryl-threonine",

abstract = "Recently observed unusual chemical reactivities of the N-phosphoryl amino acids reveal a special hexa-coordinate phosphorus intermediate may exist in the reaction process. It looks unstable and has not been observed directly. We report results obtained from ab initio studies of dimethyloxyphosphoryl-threonine and the corresponding hexa-coordinate phosphorus intermediate. The calculated results show that the hexa-coordinate phosphorous intermediate is a stable structure and all the PO and PN bonds in the intermediate should be much more active. From the calculated results, it is very easy to understand the observed reactivities of dimethyloxyphosphoryl-threonine and other similar dialkyloxyphosphoryl amino acids.",

author = "Zhan, {Chang Guo} and Suehiro Iwata",

note = "Funding Information: This project was partially supported by Grant-in-Aids for Scientific Research (No. 04243102) and for Priority Area (04640458) of the Ministry of Education, Science and Culture of Japan, and by the Excellent University Teacher's Foundation of the State Education Commission of China. One of the authors (CGZ) wishes to thank the Japan Society for Promotion of Science for providing financial support (JSPS RONPAKU Fellow program) to his stay at the Institute for Molecular Science and to thank Professor Y.F. Zhao for introducing their interesting experimental results to him.",

year = "1995",

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language = "English",

volume = "247",

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T1 - Ab initio studies on structures of the hexa-coordinate phosphorus intermediate for the phosphoryl ester exchange and N → O migration reactions of dimethyloxyphosphoryl-threonine

AU - Zhan, Chang Guo

AU - Iwata, Suehiro

N1 - Funding Information: This project was partially supported by Grant-in-Aids for Scientific Research (No. 04243102) and for Priority Area (04640458) of the Ministry of Education, Science and Culture of Japan, and by the Excellent University Teacher's Foundation of the State Education Commission of China. One of the authors (CGZ) wishes to thank the Japan Society for Promotion of Science for providing financial support (JSPS RONPAKU Fellow program) to his stay at the Institute for Molecular Science and to thank Professor Y.F. Zhao for introducing their interesting experimental results to him.

PY - 1995/12/29

Y1 - 1995/12/29

N2 - Recently observed unusual chemical reactivities of the N-phosphoryl amino acids reveal a special hexa-coordinate phosphorus intermediate may exist in the reaction process. It looks unstable and has not been observed directly. We report results obtained from ab initio studies of dimethyloxyphosphoryl-threonine and the corresponding hexa-coordinate phosphorus intermediate. The calculated results show that the hexa-coordinate phosphorous intermediate is a stable structure and all the PO and PN bonds in the intermediate should be much more active. From the calculated results, it is very easy to understand the observed reactivities of dimethyloxyphosphoryl-threonine and other similar dialkyloxyphosphoryl amino acids.

AB - Recently observed unusual chemical reactivities of the N-phosphoryl amino acids reveal a special hexa-coordinate phosphorus intermediate may exist in the reaction process. It looks unstable and has not been observed directly. We report results obtained from ab initio studies of dimethyloxyphosphoryl-threonine and the corresponding hexa-coordinate phosphorus intermediate. The calculated results show that the hexa-coordinate phosphorous intermediate is a stable structure and all the PO and PN bonds in the intermediate should be much more active. From the calculated results, it is very easy to understand the observed reactivities of dimethyloxyphosphoryl-threonine and other similar dialkyloxyphosphoryl amino acids.

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JO - Chemical Physics Letters

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ER -

Ab initio studies on structures of the hexa-coordinate phosphorus intermediate for the phosphoryl ester exchange and N → O migration reactions of dimethyloxyphosphoryl-threonine

Abstract

Bibliographical note

Funding

ASJC Scopus subject areas

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