31P NMR AND COMPUTATIONAL STUDIES ON STEREOCHEMISTRY OF CONVERSION OF PHOSPHORAMIDATE DIESTERS INTO THE CORRESPONDING PHOSPHOTRIESTERS

被引：1

作者：

Soderberg, Linda ^{[1
]}

Laven, Gaston ^{[1
]}

Kalek, Marcin ^{[1
]}

Stawinski, Jacek ^{[1
,2
]}

机构：

[1] Stockholm Univ, Dept Organ Chem, Arrhenius Lab, S-10691 Stockholm, Sweden

[2] Polish Acad Sci, Inst Bioorgan Chem, Poznan, Poland

来源：

NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS | 2011年 / 30卷 / 7-9期

基金：

瑞典研究理事会;

关键词：

Phosphoramidates; nitrite-promoted rearrangement; phosphotriesters; DFT calculations; edge attack; SN2(P); DENSITY-FUNCTIONAL THERMOCHEMISTRY; NUCLEOSIDE H-PHOSPHONATES; ALKYL-N-NITROSOAMIDES; PHOSPHORUS; CHEMISTRY; OLIGONUCLEOTIDES; SILICON; RIBOOLIGONUCLEOTIDES; ANALOGIES; MECHANISM;

D O I：

10.1080/15257770.2011.586009

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

P-31 NMR spectroscopy was used to investigate a stereochemical course of a nitrite-promoted conversion of phosphoramidate diesters into the corresponding phosphotriesters. It was found that this reaction occurred with almost complete epimerization at the phosphorus center and at the C1 atom in the amine moiety. On the basis of the P-31 NMR data, a plausible mechanism for the reaction was proposed. The density functional theory calculation of the key step of the reaction, i.e., breaking of the P-N bond and formation of the P-O bond, suggested a one-step S(N)2(P) process with retention of configuration at the phosphorus center.

引用

页码：552 / 564

页数：13

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