Stereoelectronic control in carbon-oxygen and phosphorus-oxygen bond breaking processes. ab initio calculations and speculations on the mechanism of action of ribonuclease A, staphylococcal nuclease, and lysozyme

David G. Gorenstein, John B. Findlay, Bruce A. Luxon, Debojyoti Kar

Research output: Contribution to journalArticlepeer-review

94 Scopus citations

Abstract

Ab initio molecular orbital calculations on dimethyl phosphate monoanion and dimethoxymethane demonstrate that antiperiplanar ester oxygen lone pairs significantly perturb the X-O (X = P or C) bond overlap populations. Specifically molecules in a gauche,trans conformation are "activated" for cleavage of the trans X-O bond. Other consequences of this torsional activation are discussed and presented in the context of a mechanism of action of ribonuclease A, staphylococcal nuclease, and lysozyme.

Original languageEnglish (US)
Pages (from-to)3473-3479
Number of pages7
JournalJournal of the American Chemical Society
Volume99
Issue number10
StatePublished - 1977
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

Fingerprint Dive into the research topics of 'Stereoelectronic control in carbon-oxygen and phosphorus-oxygen bond breaking processes. ab initio calculations and speculations on the mechanism of action of ribonuclease A, staphylococcal nuclease, and lysozyme'. Together they form a unique fingerprint.

Cite this