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1. Diverting thiamin from catalysis to destruction. Mechanism of fragmentation of N(1')-methyl-2-(1-hydroxybenzyl)thiamin

Author

Kluger, Ronald, Lam, John Francis, Pezacki, John Paul, and Yang, Chi-Ming

Subjects
Vitamin B1 -- Research, Scission (Chemistry) -- Analysis, Chemical reactions -- Observations, Chemistry
Abstract

The fragmentation of N(1')-methyl-2-(1-hydroxybenzyl)thiamin (MBzT) is a first-order reaction and involves the protonation of the pyrimidine. The fragmentation of MBzT involves an initial loss of the C(2-alpha) proton of the pyrimidine to give an intermediate enamine. This zwitterion suffers cleavage at the C-N bond but no benzaldehyde is formed. However in alkaline solutions 2-(1-hydroxybenzyl)thiamin gives benzaldehyde and thiamin.

Published
1995

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