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A Model Compound of the Novel Organic Cofactor CTQ (Cysteine Tryptophylquinone) of Quinohemoprotein Amine Dehydrogenase
Author(s) -
Murakami Yoko,
Tachi Yoshimitsu,
Itoh Shinobu
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400191
Subject(s) - chemistry , amine gas treating , cofactor , thioether , cysteine , substituent , stereochemistry , organic chemistry , combinatorial chemistry , enzyme
A model compound of the novel organic cofactor CTQ (cysteine tryptophylquinone) of quinohemoprotein amine dehydrogenase (QH‐AmDH) has been synthesized for the first time by the Michael addition of phenylmethanethiol to the 3‐methyl‐6,7‐indolequinone derivative as a key step. The model compound replicates the characteristic absorption spectrum of native CTQ as well as its redox potential in the γ subunit of QH‐AmDH. Detailed structural and spectroscopic characterizations of the model compound have provided important insights into the substituent effects of the thioether group of CTQ. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)