doi: 10.1021/ja804577q.
Epub 2008 Sep 3.
Artificial enzymes with thiazolium and imidazolium coenzyme mimics
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- PMID: 18763766
- PMCID: PMC2668524
- DOI: 10.1021/ja804577q
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Artificial enzymes with thiazolium and imidazolium coenzyme mimics
J Am Chem Soc.
.
Abstract
Hydrophobic thiazolium and imidazolium coenzyme mimics in the presence of modified-polyethylenimine enzyme mimics catalyze the benzoin condensation 2300-3300 times faster than the coenzyme mimics alone. Polycationic enzyme mimics provide not only a hydrophobic binding domain for coenzyme and substrate, but also electrostatic stabilization of anionic species that arise along the reaction pathway of the benzoin condensation.
Figures
Thiamine diphosphate (1) and zwitterion/carbene resonance hybrids of thiazolium (2/3) and imidazolium (5/6) ions.
Neutral (11 and 12) and polycationic (13) PEIs.
Benzoin (10) formation catalyzed by thiazolium (or imidazolium) ions
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