Making thiamin work faster: acid-promoted separation of carbon dioxide.

@article{Hu2005MakingTW,
  title={Making thiamin work faster: acid-promoted separation of carbon dioxide.},
  author={Qingyan Hu and R. Kluger},
  journal={Journal of the American Chemical Society},
  year={2005},
  volume={127 35},
  pages={
          12242-3
        }
}
The conjugate of thiamin and benzoylformate, mandelylthiamin (MTh), undergoes decarboxylation about 106 times slower than the analogous enzymic intermediate. It has now been discovered that the decarboxylation of MTh is accelerated by the acid component of pyridine and 4-picoline buffers. There is no role for a proton donor to stabilize the transition state for decarboxylation: catalysis must be achieved by the acid's trapping the product carbanion, preventing recarboxylation. This requires… Expand
18 Citations
Umpolung Reactivity of Aldehydes toward Carbon Dioxide.
Decarboxylation, CO2 and the reversion problem.
  • R. Kluger
  • Chemistry, Medicine
  • Accounts of chemical research
  • 2015
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