High rates and substrate selectivities in water by polyvinylimidazoles as transaminase enzyme mimics with hydrophobically bound pyridoxamine derivatives as coenzyme mimics.
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.
Skouta
Rachid
R
Department of Chemistry, Columbia University, New York, New York 10027, USA.
Wei
Sujun
S
Breslow
Ronald
R
D007093:Imidazoles / Q000737:chemistry*; D018716:Molecular Mimicry; D011145:Polyvinyls / Q000737:chemistry*; D011733:Pyridoxamine / Q000378:metabolism*; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D013056:Spectrophotometry, Ultraviolet; D013379:Substrate Specificity; D000637:Transaminases / Q000378:metabolism*; D014867:Water / Q000737:chemistry*
D007093:Imidazoles; D011145:Polyvinyls; D014867:Water; C072974:polyvinylimidazole; D011733:Pyridoxamine; D000637:Transaminases