Studies On Models For The Tetrahydrofolic Acid. IV. Reactions Of Amines With Formamidinium Tetrahydroquinoxaline Analogs

S. J. Benkovic, T. H. Barrows, P. R. Farina

Research output: Contribution to journalArticlepeer-review

41 Scopus citations

Abstract

The condensation of amines with formamidinium model compounds for 5,10-methenyltetrahydrofolic acid leads to N-formimidoyl products. The reaction involves decomposition of a presumed orthoamide intermediate to yield the formamidine product of kinetic control; the latter then isomerizes to the thermodynamically more stable N-formimidoyl derivative. In the absence of intramolecular effects, efficient transfer of the one-carbon unit to yield the N-formyl amine generally requires the pKa of the condensing amine to be less than the pKa of the formamidine nitrogens owing to the need for amine protonation prior to expulsion. The implications of kinetic vs. thermodynamic control for the mechanisms of folate catalyzed transfer reactions are discussed.

Original languageEnglish (US)
Pages (from-to)8414-8420
Number of pages7
JournalJournal of the American Chemical Society
Volume95
Issue number25
DOIs
StatePublished - Dec 1 1973

All Science Journal Classification (ASJC) codes

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

Fingerprint Dive into the research topics of 'Studies On Models For The Tetrahydrofolic Acid. IV. Reactions Of Amines With Formamidinium Tetrahydroquinoxaline Analogs'. Together they form a unique fingerprint.

Cite this