Theoretical prediction of 31P NMR chemical shifts of intermediates in phosphoryl ester exchange and N → O migration reactions of dialkyloxyphosphoryl amino acid

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Abstract

Based on a detailed ab initio study on the reaction mechanism of phosphoryl ester exchange and N → O migration reactions of dimethyloxyphosphoryl-threonine, ab initio GIAO magnetic shielding calculations have been carried out on the predicted stable intermediate and the corresponding reactant and product. The 31P NMR chemical shift of the most stable penta-coordinate phosphorus intermediate has been predicted as about -71 ppm. The theoretical results may lead to a possible way to experimentally examine our predictions and to monitor the most stable intermediate during the reaction process.

Original languageEnglish
Pages (from-to)655-658
Number of pages4
JournalPhosphorus, Sulfur and Silicon and Related Elements
Volume144-146
DOIs
StatePublished - 1999

Keywords

  • P NMR chemical shift
  • Phosphorylated amino acid
  • Reaction mechanism

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Inorganic Chemistry

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