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Mithoron
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Acidity of thiamine - how comes hydroxide anion with pK about 15 ionizes thiamine with pK about 18?

Textbooks say removing proton from thiamine's C atom will produce a resonance stabilized carbanion which is hence bioactive. That's OK, but how comes that 1) we abstract the acidic proton with the OH base whose pK is lower that for thiamine, and 2) the remaining anion acts - in bio context - in aqua medium (?), hence will immediately deprotonate water and lose its negative charge.

deprotonation of thiamine's thiazolium ring