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Stereochemistry of 2-Phenylethylamine Oxidation Catalyzed by Bacterial Copper Amine Oxidase
Author(s) -
Mayumi Uchida,
Akifumi OHTANI,
Naoki Kohyama,
Toshihide Okajima,
Katsuyuki Tanizawa,
Yukio Yamamoto
Publication year - 2003
Publication title -
bioscience biotechnology and biochemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.509
H-Index - 116
eISSN - 1347-6947
pISSN - 0916-8451
DOI - 10.1271/bbb.67.2664
Subject(s) - chemistry , phenylacetaldehyde , stereospecificity , amine gas treating , amine oxidase , copper , deuterium , catalysis , substrate (aquarium) , hydrogen atom abstraction , amine oxidase (copper containing) , gas chromatography , enzyme , mass spectrometry , enzyme catalysis , stereochemistry , organic chemistry , hydrogen , chromatography , diamine oxidase , physics , oceanography , quantum mechanics , geology
The stereochemical course of the reaction catalyzed by a copper amine oxidase from Arthrobacter globiformis has been investigated using 2-phenylethylamine stereospecifically deuterium-labeled at the C1 position. Measurements of deuterium content in the product, phenylacetaldehyde, by gas chromatography-mass spectrometry revealed stereospecific abstraction of the pro-S hydrogen during the enzymatic oxidation, as predicted from the structure modeling for the enzyme-bound substrate.

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