? 1-Pyrrolin und? 1-Piperidein aus Putrescin und Cadaverin durch enzymatische Oxydation

Hasse, Karl; Maisack, H.

doi:10.1007/bf00621716

Cited by 18 publications

(5 citation statements)

References 3 publications

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“…From the experiments with deuteriated cadaverine (3,18,19) it can be inferred that, on the route to the alkaloids, loss of one of the two amino groups of cadaverine is accompanied by removal of the si-hydrogen atom from the adjacent enantiotopic -CH2group. This is the hydrogen atom that is known to be lost in the course of the conversion of cadaverine into the corresponding aldehyde, 5-aminopentanal (7) (or rather the corresponding Schiff base, A'-piperideine (S), into which 5-aminopentanal is spontaneously transformed (27)),2 by oxidative deamination, catalyzed by diamine oxidase (27,31) (EC 1.4.3.6), or by 2The spontaneous pH-dependent conversion of 5-aminopentanal into A'-piperideine, and thence into the corresponding dimer and trimers, has been the subject of detailed investigations (28,29). These spontaneous conversions were not taken into account in a proposed biosynthetic model (22,30), which has now been disproved (20,21).…”

Section: Introductionmentioning

confidence: 99%

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Biosynthesis of the lupine alkaloids. II. Sparteine and lupanine

Golebiewski¹,

Spenser²

1988

Can. J. Chem.

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Contrary to predictions based on earlier observations, it is now found that label from DL-[6-14C]lysine and from [6-14C]-Δ1-piperideine does not enter the three C5 segments of lupanine with equal efficiency. One of the C5 segments is labelled at a significantly higher level than the other two C5 segments, which show identical levels of labelling. A new biogenetic model is proposed, which is consistent with these new findings as well as with all other regio- and stereochemical evidence on the mode of incorporation of precursors that is available.

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Section: Introductionmentioning

confidence: 99%

“…~~-[6-'"~]Lysine monohydrochloride (Scheme 7) Ethyl 2-ace~lamino-2-ethoxycarbonyl-5-hydroxypentanoate (ref. 44)(28). Diethyl acetamidomalonate (26) (10.9 g) was added to a suspension of freshly prepared sodium methoxide (from 18 mg sodium metal) in dry benzene(17 mL).…”

mentioning

confidence: 99%

Biosynthesis of the lupine alkaloids. II. Sparteine and lupanine

Golebiewski¹,

Spenser²

1988

Can. J. Chem.

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“…Putrescine could arise either from arginine, via agmatine and Ncarbamylputrescine (Smith, 1968), or by the decarboxylation of ornithine. 4-Aminobutyraldehyde, a known putrescine metabolite (Tabor, 1951;Mann and Smithies, 1955;Hasse and Maisack, 1955;Kim and Tchen, 1962), would seem particularly attractive. These possibilities are currently under investigation.…”

Section: Discussionmentioning

confidence: 99%

sym-Homospermidine, a naturally occurring polyamine

Kuttan¹,

Radhakrishnan²,

Spande³

et al. 1971

Biochemistry

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“…Die im Vergleich zur Nz-Abspaltung aus anderen Alkylaziden R -N3 niedrige Thermolyse-Temperatur 3t1, [17][18][19] laDt sich durch einen Nachbargruppen-Effekt der C = C-Doppelbindung erklaren, welcher den synchronen") RingschluD zum gespannten 2H-Azirin erleichtert [Gl. (7)]. …”

Section: A Pe-spektroskopische Optimierung Der Gasphasen-unclassified

Gasphasen‐Reaktionen, 61¹⁾ Cycloalkanimine 2H‐Azirin, 1‐Azetin, 1‐Pyrrolin, 1‐Piperidein und 3,4,5,6‐Tetrahydro‐2H‐azepin: Darstellung und Photoelektronen‐Spektren^2,3)

Bock

Dammel

1987

Chem. Ber.

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Zur Darstellung der oligomerisationsfreudigen Cycloalkanimine ( H 2 m N werden folgende Gasreaktionen PE-spektroskopisch optimiert: Fur das Dreiring-Imin 2H-Azirin die heterogene KOR-Dehydrochlorierung von 2-Chlorethylazid mit anschlieknder Thermolyse des entstehenden Vinylazids und fur die grokren Ringe 1-Azetin (n = 2), 1-Pyrrolin (n = 3), 1-Piperidein (n = 4) sowie das siebengliedrige 3,4,5,6-Tetrahydro-2H-azepin die Chlorierung des betreffenden Cycloalkylamins an festem N-Chlorsuccinimid mit darauffolgender KOR-Dehydrochlorierung des gebildeten N-Chlor-Derivates. Die PE-Spektren aller dargestellten Cycloalkanimine werden anhand Geometrie-optimierter MNDO-Berechnungen zugeordnet und ihre Elektronenstrukturen durch Molekiilzustandsvergleich mit steigender Ringgrok sowie mit der isoelektronischen Reihe der Cycloalkene diskutiert. Die thermische RingBffnung von 1-Azetin zu 2-Azabutadien laDt sich mit PE-spektroskopischer Echtzeit-Gasanalytik gut verfolgen; sein lonisationsmuster wird durch Vergleich mit anderen Azabutadienen zugeordnet.

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? 1-Pyrrolin und? 1-Piperidein aus Putrescin und Cadaverin durch enzymatische Oxydation

Cited by 18 publications

References 3 publications

Biosynthesis of the lupine alkaloids. II. Sparteine and lupanine

Biosynthesis of the lupine alkaloids. II. Sparteine and lupanine

sym-Homospermidine, a naturally occurring polyamine

Gasphasen‐Reaktionen, 61¹⁾ Cycloalkanimine 2H‐Azirin, 1‐Azetin, 1‐Pyrrolin, 1‐Piperidein und 3,4,5,6‐Tetrahydro‐2H‐azepin: Darstellung und Photoelektronen‐Spektren^2,3)

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? 1-Pyrrolin und? 1-Piperidein aus Putrescin und Cadaverin durch enzymatische Oxydation

Cited by 18 publications

References 3 publications

Biosynthesis of the lupine alkaloids. II. Sparteine and lupanine

Biosynthesis of the lupine alkaloids. II. Sparteine and lupanine

sym-Homospermidine, a naturally occurring polyamine

Gasphasen‐Reaktionen, 611) Cycloalkanimine 2H‐Azirin, 1‐Azetin, 1‐Pyrrolin, 1‐Piperidein und 3,4,5,6‐Tetrahydro‐2H‐azepin: Darstellung und Photoelektronen‐Spektren2,3)

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Gasphasen‐Reaktionen, 61¹⁾ Cycloalkanimine 2H‐Azirin, 1‐Azetin, 1‐Pyrrolin, 1‐Piperidein und 3,4,5,6‐Tetrahydro‐2H‐azepin: Darstellung und Photoelektronen‐Spektren^2,3)