Transamination reactions with multiple turnovers catalyzed by hydrophobic pyridoxamine cofactors in the presence of polyethylenimine polymers

Journal of the American Chemical Society

Volumn 126, Issue 26, 2004, Pages 8136-8137

  Liu, Lei ^a   Zhou, Wenjun ^a   Chruma, Jason ^a   Breslow, Ronald ^a  

^a Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

POLYETHYLENEIMINE; POLYMER; PYRIDOXAMINE;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; COVALENT BOND; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HIGH TEMPERATURE; HYDROPHOBICITY; MOLECULAR INTERACTION; REACTION ANALYSIS; TRANSAMINATION;

HYDROPHOBICITY; MOLECULAR STRUCTURE; POLYETHYLENEIMINE; POLYMERS; PYRIDOXAMINE; PYRUVIC ACID; SUBSTRATE SPECIFICITY; TRANSAMINASES;

EID: 3042811413     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja048671a     Document Type: Article

References (12)

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7. Polyethylenimine used in this study is a branched polymer which has a molecular weight of ca. 60000, containing ca. 1400 monomeric ethylamine residues. About 25% of the amino groups are primary, about 50% are secondary, and about 25% are tertiary.
8. Breslow, R.; Hammond, M.; Lauer, M. J. Am. Chem. Soc. 1980, 102, 421
9. 2 (see: Imperiali, B.; Roy, R. S. J. Org. Chem. 1995, 60, 1891).
10. Oxidative decarboxylation has also been studied very recently. See: Zabinski, R. F.; Toney, M. D. J. Am. Chem. Soc. 2001, 123, 193.
11. It was previously proposed that an apolar environment could greatly enhance the decarboxylation reactivity. (Askley, J. A.; Lo, C.-H. L.; McElhaney, G. P.; Wirsching, P.; Janda, K. D. J. Am. Chem. Soc. 1993, 115, 2515.)
12. We also tried dimethylglycine and diphenylglycine as sacrificial reagent. The former one showed too low reactivity. The latter one reacted with ketoacid, directly yielding diphenyl ketone in the absence of pyridoxal. This caused a significant background reaction. Additionally, the resulting diphenylmethyleneimine of 7 did not hydrolyze readily under the reaction conditions.