Oxidation of N-alkylputrescines by diamine oxidases

Cooper, Alan; Equi, Angela M.; Ner, S. K.; Watson, Allan B.; Robins, David J.

doi:10.1016/s0040-4039(01)93476-8

Cited by 6 publications

(3 citation statements)

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“…DAOs catalyse the oxidative deamination of many substrates, such as N ‐alkylputrescines, 111 triazolyl alkyl amines, 112 p ‐chlorophenylethylamine and β‐substituted ethylenediamines. 113 For instance, a DAO from Phialemonium sp.…”

Section: Enzyme Catalysed Aldehyde Formationmentioning

confidence: 99%

Enzymatic reactions towards aldehydes: An overview

Schober

Dobiašová

Jurkaš

et al. 2023

Flavour & Fragrance J

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Many aldehydes are volatile compounds with distinct and characteristic olfactory properties. The aldehydic functional group is reactive and, as such, an invaluable chemical multi‐tool to make all sorts of products. Owing to the reactivity, the selective synthesis of aldehydic is a challenging task. Nature has evolved a number of enzymatic reactions to produce aldehydes, and this review provides an overview of aldehyde‐forming reactions in biological systems and beyond. Whereas some of these biotransformations are still in their infancy in terms of synthetic applicability, others are developed to an extent that allows their implementation as industrial biocatalysts.

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Section: Enzyme Catalysed Aldehyde Formationmentioning

confidence: 99%

Enzymatic reactions towards aldehydes: An overview

Schober

Dobiašová

Jurkaš

et al. 2023

Flavour & Fragrance J

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“…Finally incubation of [2,2,5,5-2~4]-1,6-diaminohexane (13) dihydrochloride with DAO as in the previous two cases afforded a sample of the seven-membered derivative (16) in 75% yield. The region 6 1.0-1.6 in the 'H NMR spectrum of 1 6 integrated for four protons compared to eight in the corresponding spectrum for 10.…”

Section: Introductionmentioning

confidence: 95%

“…With the surprising exception of N-methylputrescine, these diamines were shown to be oxidized to the corresponding aminoaldehydes. We repeated this work using an improved kinetic assay procedure, and demonstrated that N-methylputrescine was in fact a good substrate for pea seedling and pig kidney DAO (13). A range of derivatives of 1 h his paper is dedicated to Professor Ian Spenser, an acknowledged expert in the determination of the stereochemistry of enzymic reactions and the elucidation of biosynthetic pathways to alkaloids.…”

Section: Introductionmentioning

confidence: 99%

Mechanistic studies on diamine oxidase: oxidation of α,ω-diamines does not involve an enamine intermediate

Gavin¹,

Equi²,

Robins³

1994

Can. J. Chem.

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ROBINS. Can. 72, 31 (1994).Three labelled labe labelled a,o-diarnines were synthesized and incubated with pea seedling diamine oxidase. The aminoaldehydes formed by oxidative deamination cyclized to the corresponding imines, which were trapped with benzoylacetic acid. In all three cases the acetophenone derivatives produced were shown by NMR and mass spectrometry to contain four deuterium atoms. The retention of all four deuterium atoms demonstrates that oxidative deamination of a,o-diamines catalyzed by pea seedling diamine oxidase does not involve an enarnine intermediate as previously suggested. STEPHEN S. GAVIN, ANGELA M. EQUI et DAVID J. ROBINS. Can. 72,31 (1994).On a synthktisk trois ~,~.~' ,~' -~~~-a , o -d i a m i n e s et on les a incubtes avec de la diarnine oxydase de la semence de pois. Les trois arninoaldkhydes qui se forment par dksamination oxydante se cyclisent en irnines correspondantes que l'on peut pitger a l'aide d'acide benzoylacktique. Dans les trois cas, on a dkmontrk, par RMN et par spectromttrie de rnasse, que les dkrivks acetophknones qui se forment contiennent toutes quatre atomes de deutkrium. La rktention des quatre atomes de deutkrium dtrnontre que, contrairement h ce qui avait kt6 suggtrt antkrieurement, la dksamination oxydante des a,odiamines catalyske par la diamine oxydase de la semence de pois n'irnplique pas d'interrntdiaire knamine.[Traduit par la redaction] Introduction Decarboxylation of basic a-amino acids such as ornithine and lysine followed by the oxidative deamination of the resulting diamines, putrescine (1) and cadaverine (2), respectively, are key steps in amino acid metabolism and the biosynthesis of many alkaloids (1). Naturally occurring polyamines such as 1 also have an important function in the control of growth and proliferation processes (2). Putrescine is formed by decarboxylation of L-ornithine catalyzed by L-ornithine decarboxylase. The stereochemistry of this process was studied by several groups of workers (3-7). An analogous process operates on the homologue L-lysine, which leads to cadaverine on decarboxylation with L-lysine decarboxylase. Again this process was shown to proceed with retention of configuration (6-9). The next step in the metabolism of the diamines 1 and 2 is oxidative deamination to the corresponding aldehydes 5 and 6 catalyzed by diamine oxidase (DAO, EC 1.4.3.6) (Scheme 1). The stereochemistry of these processes was studied extensively by 10) and by other groups of workers (9, 11). DAO catalyses the removal of the 1-pro-S hydrogen from 1 and 2.A series of N-alkylputrescines was tested as substrates of DAO by Frydman et al. (12). With the surprising exception of N-methylputrescine, these diamines were shown to be oxidized to the corresponding aminoaldehydes. We repeated this work using an improved kinetic assay procedure, and demonstrated that N-methylputrescine was in fact a good substrate for pea seedling and pig kidney DAO (13). A range of derivatives of 1

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