ISSN:
1434-193X
Keywords:
Bioorganic chemistry
;
Metalloenzymes
;
Enzyme catalysis
;
O-O activation
;
C-H activation
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The three-dimensional aspects of the chemistry of dopamine β-hydroxylase (DBH) was studied through a conformationally-restricted substrate analog approach. We found that the DBH-catalyzed hydroxylation of 2-aminoindane (1) exclusively produced the trans-(1S,2S)-2-amino-1-indanol (4S) (93% ee) in contrast to the stereochemical course of the pro-R hydroxylation of the DBH/phenethylamine reaction. Studies with stereospecifically deuterium labeled 2-aminoindanes 2 and 3 show that the production of (1S)-aminoindanol 4S is the result of stereospecific pro-S hydrogen abstraction followed by the oxygen binding with overall retention of configuration. On the basis of these findings, we propose a model for the interaction of the phenethylamine substrates with the enzyme.
Type of Medium:
Electronic Resource
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