Studies on Models for Tetrahydrofolic Acid. I. The Condensation of Formaldehyde with Tetrahydroquinoxaline Analogs

Stephen J. Benkovic, Patricia A. Benkovic, David R. Comfort

Research output: Contribution to journalArticle

47 Citations (Scopus)

Abstract

To investigate the mechanisms of tetrahydrofolic acid catalyzed one carbon unit transfers, we have synthesized several tetrahydroquinoxaline analogs. A kinetic investigation of the condensation with formaldehyde of one of these models reveals the intermediacy of the iminium cation as a steady-state species and the importance of general catalysis in formation of the imidazolidine ring, the latter a model for 5,10-methylenetetra-hydrofolic acid. The relevance of these results to the mechanism of one carbon unit transfers and the importance of certain structural and electronic features in the actual cofactor are discussed.

Original languageEnglish (US)
Pages (from-to)5270-5279
Number of pages10
JournalJournal of the American Chemical Society
Volume91
Issue number19
DOIs
StatePublished - Sep 1 1969

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Formaldehyde
Condensation
Carbon
Imidazolidines
Acids
Catalysis
Cations
Positive ions
Kinetics
5,6,7,8-tetrahydrofolic acid

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Benkovic, Stephen J. ; Benkovic, Patricia A. ; Comfort, David R. / Studies on Models for Tetrahydrofolic Acid. I. The Condensation of Formaldehyde with Tetrahydroquinoxaline Analogs. In: Journal of the American Chemical Society. 1969 ; Vol. 91, No. 19. pp. 5270-5279.
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Studies on Models for Tetrahydrofolic Acid. I. The Condensation of Formaldehyde with Tetrahydroquinoxaline Analogs. / Benkovic, Stephen J.; Benkovic, Patricia A.; Comfort, David R.

In: Journal of the American Chemical Society, Vol. 91, No. 19, 01.09.1969, p. 5270-5279.

Research output: Contribution to journalArticle

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