Organic and Biological Chemistry

Studies on Models for Tetrahydrofolic Acid. II. Additional Observations on the Mechanism for Condensation of Formaldehyde with Tetrahydroquinoxaline Analogs

Stephen Benkovic, Patricia Ann Benkovic, Robert Chrzanowski

Research output: Contribution to journalArticle

33 Citations (Scopus)

Abstract

The condensation of formaldehyde with additional tetrahydroquinoxaline model systems in which the basicity of the exocyclic amino group has been varied through alterations in para substitution has been studied. Supporting evidence for a mechanism involving general base catalysis of attack by the exocyclic amino group on the iminium cation to yield the imidazolidine adduct is derived from these investigations. Experiments with a similar tetrahydroquinoline model indicate the importance of the nitrogen-8 of the tetrahydropyrazine ring on the rate of acid-catalyzed dehydration of the intermediate carbinolamine. The implication of these results as to the mechanism of action of the natural cofactor is discussed.

Original languageEnglish (US)
Pages (from-to)523-528
Number of pages6
JournalJournal of the American Chemical Society
Volume92
Issue number3
DOIs
StatePublished - Feb 1 1970

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Imidazolidines
Organic Chemistry
Catalysis
Dehydration
Formaldehyde
Cations
Condensation
Nitrogen
Acids
Alkalinity
Substitution reactions
Positive ions
Experiments
5,6,7,8-tetrahydrofolic acid
1,2,3,4-tetrahydroquinoline

All Science Journal Classification (ASJC) codes

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

Cite this

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abstract = "The condensation of formaldehyde with additional tetrahydroquinoxaline model systems in which the basicity of the exocyclic amino group has been varied through alterations in para substitution has been studied. Supporting evidence for a mechanism involving general base catalysis of attack by the exocyclic amino group on the iminium cation to yield the imidazolidine adduct is derived from these investigations. Experiments with a similar tetrahydroquinoline model indicate the importance of the nitrogen-8 of the tetrahydropyrazine ring on the rate of acid-catalyzed dehydration of the intermediate carbinolamine. The implication of these results as to the mechanism of action of the natural cofactor is discussed.",
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Organic and Biological Chemistry : Studies on Models for Tetrahydrofolic Acid. II. Additional Observations on the Mechanism for Condensation of Formaldehyde with Tetrahydroquinoxaline Analogs. / Benkovic, Stephen; Benkovic, Patricia Ann; Chrzanowski, Robert.

In: Journal of the American Chemical Society, Vol. 92, No. 3, 01.02.1970, p. 523-528.

Research output: Contribution to journalArticle

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