The oxidation of 1‐alkyl(aryl)quinolinium chlorides with rabbit liver aldehyde oxidase

Angelino, S.A.G.F.; VALKENGOED, B. H. VAN; Buurman, D. J.; Plas, H. C. Van Der; Müller, Franz

doi:10.1002/jhet.5570210123

Cited by 9 publications

References 25 publications

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Purification and immobilization of rabbit liver aldehyde oxidase

Angelino

Müller

Plas

1985

Biotech & Bioengineering

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Aldehyde oxidase (E.C. 1.2.3.1) was isolated from rabbit liver and two potential bioaffinity ligands, i.e., 3-aminocarbonyl-1-benzyl-6-methylpyridinium bromide and 3-aminocarbonyl-1-benzyl-4,6-dimethylpyridinium chloride, were tested for their applicability in a purification procedure for this enzyme. Various supports and different coupling methods were investigated for the immobilization of aldehyde oxidase. Adsorption to n-hexyl- and n-octylamine-substituted Sepharose 4B and DEAE Sepharose 6B gave the best retention of aldehyde oxidase activity. The storage stability of free enzyme and enzyme immobilized to n-octylamine-substituted Sepharose 4B was studied in several buffers at pH 7.8 and 9.0. This showed that the stability of immobilized enzyme was much less than that of free enzyme. The apparent operational stability of the immobilized enzyme preparation, however, improved substantially compared to soluble enzyme, although the corresponding product yield is still very poor. Coimmobilization of catalase and/or superoxide dismutase provided no significant increase of the apparent operational stability and product yield. A positive effect on both parameters was found for aldehyde oxidase-n-alkylamine Sepharose 4B preparations by increasing the amount of enzyme adsorbed per unit weight of support, whereas the productivity of these preparations remained about constant.

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Purification and immobilization of rabbit liver aldehyde oxidase

Angelino

Müller

Plas

1985

Biotech & Bioengineering

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ChemInform Abstract: THE OXIDATION OF 1‐ALKYL(ARYL)QUINOLINIUM CHLORIDES WITH RABBIT LIVER ALDEHYDE OXIDASE

Angelino¹,

VALKENGOED²,

Buurman³

et al. 1984

Chemischer Informationsdienst

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Imination of N‐methylazinium salts by liquid ammonia/potassium permanganate

Woźniak¹,

Buurman²,

Plas³

1985

Journal of Heterocyclic Chem

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Treatment of 1‐methylquinolinium‐, 1,4‐dimethylquinolinium‐ and 1‐methyl‐1,X‐naphthyridinium iodides (X = 5,8) with liquid ammonia/potassium permanganate leads to introduction of the imino group at C‐2 forming the 1,2‐dihydro‐2‐imino‐1‐methylquinolines and 1,2‐dihydro‐2‐imino‐1‐methyl‐1,X‐naphthyridines (X = 5,8) respectively. 1,2‐Dimethylquinolinium iodide, when subjected to treatment with liquid ammonia/potassium permanganate undergoes an oxo‐demethylation reaction, yielding 1‐methylquinol‐2‐one. The nmr‐measurements of solutions of the above‐mentioned salts in liquid ammonia clearly show the formation of a σ‐adduct, strongly suggesting that these σ‐adducts are intermediates in the imination reactions.

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The oxidation of 1‐alkyl(aryl)quinolinium chlorides with rabbit liver aldehyde oxidase

Cited by 9 publications

References 25 publications

Purification and immobilization of rabbit liver aldehyde oxidase

Purification and immobilization of rabbit liver aldehyde oxidase

ChemInform Abstract: THE OXIDATION OF 1‐ALKYL(ARYL)QUINOLINIUM CHLORIDES WITH RABBIT LIVER ALDEHYDE OXIDASE

Imination of N‐methylazinium salts by liquid ammonia/potassium permanganate

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