Stability of the 6-carbanion of uracil analogues: mechanistic implications for model reactions of orotidine-5'-monophosphate decarboxylase

Freeman M Wong; Christina C Capule; Weiming Wu

doi:10.1021/ol0624981

Stability of the 6-carbanion of uracil analogues: mechanistic implications for model reactions of orotidine-5'-monophosphate decarboxylase

Org Lett. 2006 Dec 21;8(26):6019-22. doi: 10.1021/ol0624981.

Authors

Freeman M Wong¹, Christina C Capule, Weiming Wu

Affiliation

¹ Department of Chemistry and Biochemistry, San Francisco State University, San Francisco, California 94132, USA.

Abstract

[Structure: see text] The pKa's of the 6-CH groups of N-methyl-2-pyridone and N-methyl-4-pyridone in aqueous solution were determined. No correlation between the stability of the carbanions and the rate of decarboxylation of the corresponding carboxylic acids was found.

Publication types

Research Support, N.I.H., Extramural
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Kinetics
Magnetic Resonance Spectroscopy
Models, Chemical
Orotidine-5'-Phosphate Decarboxylase / chemistry*
Uracil / analogs & derivatives*
Uracil / chemistry

Substances

Uracil
Orotidine-5'-Phosphate Decarboxylase

Abstract

Publication types

MeSH terms

Substances

Grants and funding