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. 2008 Sep 24;130(38):12590-1.
doi: 10.1021/ja804577q. Epub 2008 Sep 3.

Artificial enzymes with thiazolium and imidazolium coenzyme mimics

Huanyu Zhao  1 , Frank W Foss Jr, Ronald Breslow
Affiliations

Artificial enzymes with thiazolium and imidazolium coenzyme mimics

Huanyu Zhao et al. 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.

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Figures

Figure 1
Figure 1
Thiamine diphosphate (1) and zwitterion/carbene resonance hybrids of thiazolium (2/3) and imidazolium (5/6) ions.
Figure 2
Figure 2
Neutral (11 and 12) and polycationic (13) PEIs.
Scheme 1
Scheme 1
Benzoin (10) formation catalyzed by thiazolium (or imidazolium) ions
See this image and copyright information in PMC

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