A cyclic imine intermediate in the in vitro metabolic conversion of 1,6-diaminohexane to 6-aminohexanoic acid and caprolactam.
1. 3,4,5,6-Tetrahydro-2H-azepine is an intermediate in the enzyme-catalyzed conversion of 1,6-diaminohexane to 6-aminohexanoic acid and its corresponding lactam, caprolactam, by mammalian liver aldehyde oxidase. 2. Identification of metabolites was based on analysis by gas chromatography-mass spectrometry and confirmed by comparison with the properties of authentic standards. 3. The results indicate that the cell differentiating agent hexamethylene bisacetamide is converted into 1,6-diaminohexane, and its metabolism therefore involves diamine oxidase. 4. The metabolic fate of 1,6-diaminohexane is similar to that of putrescine and cadaverine in that a cyclic imine is an intermediate in the formation of metabolites with ring (lactam) and chain (amino acid) structures.
Subramanyam
B
B
Department of Medicinal Chemistry, University of Maryland, Baltimore 21201.
Callery
P S
PS
Geelhaar
L A
LA
Egorin
M J
MJ
D042931:Aldehyde Oxidase; D000445:Aldehyde Oxidoreductases / Q000378:metabolism; D006631:Amine Oxidase (Copper-Containing) / Q000378:metabolism; D000614:Aminocaproates / Q000378:metabolism*; D015119:Aminocaproic Acid / Q000378:metabolism*; D000818:Animals; D001381:Azepines / Q000378:metabolism*; D002209:Caprolactam / Q000378:metabolism*; D003959:Diamines / Q000378:metabolism*; D008401:Gas Chromatography-Mass Spectrometry; D066298:In Vitro Techniques; D008099:Liver / Q000201:enzymology / Q000378:metabolism*; D008297:Male; D051381:Rats; D011919:Rats, Inbred Strains
D000614:Aminocaproates; D001381:Azepines; D003959:Diamines; C060579:3,4,5,6-tetrahydro-2H-azepine; D002209:Caprolactam; D000445:Aldehyde Oxidoreductases; D042931:Aldehyde Oxidase; D006631:Amine Oxidase (Copper-Containing); D015119:Aminocaproic Acid; C007297:1,6-diaminohexane