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Accelerating unimolecular decarboxylation by preassociated acid catalysis in thiamin-derived intermediates: implicating Brønsted acids as carbanion traps in enzymes.
- R. Kluger, G. Ikeda, Q. Hu, P. Cao, J. Drewry
- Chemistry, Medicine
- Journal of the American Chemical Society
- 14 November 2006
Mandelylthiamin (MT) is formally the conjugate of thiamin and benzoylformate. It is the simplified analogue of the first covalent intermediate in benzoylformate decarboxylase. Although MT is the… Expand
Deuterium labeling as a test of intramolecular hydride mechanisms in the fragmentation of 2-(1-hydroxybenzyl)-N1′-methylthiamin
2-(1-Hydroxybenzyl)-N1′-methylthiamin (1b) is a model for the addition intermediate in the thiamin catalyzed benzoin condensation. However, N-alkylation alters the reactivity of the compound: instead… Expand
Fast fragmentation and slow protonation: a buffer‐dependent isotope effect in reactions of N‐methyl hydroxy(benzylthiamine) analyzed by the Keeffe–Jencks equations
The fragmentation of 2-(1-hydroxybenzyl)thiamine in neutral solution (to cleave the pyrimidine and thiazolium) has been shown to compete very effectively with elimination of benzaldehyde to produce… Expand
The Hammett Equation: Probing the Mechanism of Aromatic Semicarbazone Formation
An organic class project is described where upper-level undergraduates measure kinetic rate constants for semicarbazone formation, by reacting semicarbazide with a meta- or para-substituted… Expand