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. 2009 Nov 4;131(43):15604-5.
doi: 10.1021/ja9072589.

High rates and substrate selectivities in water by polyvinylimidazoles as transaminase enzyme mimics with hydrophobically bound pyridoxamine derivatives as coenzyme mimics

Rachid Skouta  1 , Sujun Wei, Ronald Breslow
Affiliations

High rates and substrate selectivities in water by polyvinylimidazoles as transaminase enzyme mimics with hydrophobically bound pyridoxamine derivatives as coenzyme mimics

Rachid Skouta et al. J Am Chem Soc. .

Abstract

Free-radical polymers of 4-vinylimidazole and copolymers with 1-dodecyl-4-vinylimidazole were used as enzyme mimics to transaminate pyruvic acid to alanine, phenylpyruvic acid to phenylalanine, and indole-3-pyruvic acid to tryptophan in water at pH 7.5 and 20 degrees C using pyridoxamines carrying hydrophobic side chains as coenzyme mimics. The best enzyme mimic accelerated the transamination of indole-3-pyruvic acid by a factor of 4 million relative to the rate without the polymer, a higher rate ratio than we had previously achieved with a polyaziridine-based enzyme mimic. The properties of various polyvinylimidazoles were compared, including those prepared with the RAFT modification of the polymerization process.

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Figures

Scheme 1
Scheme 1
Synthesis of P4VIm and partially dodecylated P4VIm
Scheme 2
Scheme 2
Structures of P1VIm (entry 7) and pyridoxamine derivatives
See this image and copyright information in PMC

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