On the Role of Copper in PQQ Amine Oxidases

Mondovı̀, Bruno; Riccio, Pierluigi

doi:10.1007/978-94-009-0957-1_44

Cited by 2 publications

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“…Some of them utilize an ortho-quinone cofactor to achieve transamination of primary alcohol to aldehyde. (1) This cofactor of the copper amine oxidases, a pyrroloquinoline quinone 1 (methoxatine, PQQ), was isolated from bacteria(2) and some analogous compounds were described. (3) In this preliminary work, we planned to study the oxidation of compound 5 in the aim to synthesize an indolic analogue Ζ of methoxatine 1.…”

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Oxidation of Indolo-Quinoline Structures

Barret¹,

Belaissaoui²,

Du³

et al. 1999

Heterocyclic Communications

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Oxidation of new indolo-quinoline structures was studied. Herein, the use of a new oxidizing reagent, eg sodium perxenate, and other reagents (PIFA, tBuOCI) which lead to indolenin £-JJ2 from indolic compound 5 is described.The copper amine oxydases constitute an important class of mammalian enzymes involved in endoand xenobiotic metabolism. Some of them utilize an ortho-quinone cofactor to achieve transamination of primary alcohol to aldehyde.(1) This cofactor of the copper amine oxidases, a pyrroloquinoline quinone 1 (methoxatine, PQQ), was isolated from bacteria(2) and some analogous compounds were described. (3) In this preliminary work, we planned to study the oxidation of compound 5 in the aim to synthesize an indolic analogue Ζ of methoxatine 1. The synthesis of this compound was based on the following retrosynthetic scheme:The first step was an indolisation by the Fischer reaction from 4 (4) and Phenylhydrazine, involving 5 (10,11-dihydro-2,4-dimethylpyrido(3,2,a]carbazole) in medium yield (45%). Oxidation of 5. by using Yonemitsu's conditions (DDQ-THF-H2O) (5) did not give the 10-keto compound or the corresponding phenol, but £ which was isolated in 55 % (scheme 3). The same product was obtained by several reagents (Pd-C, xylene, reflux temperature : 30%; Pd-C, decaline, reflux temperature : 26%; Mn02, xylene, room temperature : 52%). An unusual reagent, eg sodium perxenate (Na4Xe06, 6H2O) (6) in methanol-H20 (4:1)(1.5 equivalent, reflux temperature, 5h) oxidized 5 into 2 (42%); the high resolution mass spectroscopy gave Brought to you by | New York University Bobst Library Technical Services Authenticated Download Date | 2/4/15 8:06 PM

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