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• W2023172318 abstract "A new PQQ model compound [dimethyl 7-(1,4,7,10-tetraoxa-13-azacyclopentadec-13-yl)carbonyl-4,5-dihydro-4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,9-dicarboxylate, 1], in which a 1-aza-15-crown-5 group is attached through an amide linkage at the 7-position, has been synthesized in order to develop an efficient model system of calcium-containing quinoprotein alcohol dehydrogenases. It has been found that Ca2+ binds to the quinone most strongly among the alkaline earth metal ions examined (Ca2++>Sr2++≫Ba2++≫Mg2+) and the binding constant (KM) for Ca2+ is as large as 2.1×105 M−1. Formation of the C-5 hemiacetal derivatives with ethanol is also investigated spectrophotometrically to show that the alcohol-addition to the quinone is enhanced in the presence of the metal ions. In this case, Ca2+ and Sr2+ show a similar efficiency that is several times larger than that of Ba2+. Addition of a strong base such as DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) into a MeCN solution containing the metal ion complex of 1 and ethanol leads to redox reactions to give the Ca2+ complex of 1H2 (quinol form) and acetaldehyde. Kinetic studies on the redox reactions have been performed to gain insight into the mechanism of the alcohol-oxidation reaction catalyzed by the metal complexes of coenzyme PQQ." @default.
• W2023172318 created "2016-06-24" @default.
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• W2023172318 date "2000-01-01" @default.
• W2023172318 modified "2023-10-18" @default.
• W2023172318 title "Development of the active site model for calcium-containing quinoprotein alcohol dehydrogenases" @default.
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• W2023172318 doi "https://doi.org/10.1016/s1381-1177(99)00070-3" @default.
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