Model studies support pyrrolylation of the topaquinone cofactor to explain inactivation of bovine plasma amine oxidase by 3-pyrrolines. Unusual processing of a secondary amine

Journal of the American Chemical Society

Volumn 118, Issue 30, 1996, Pages 7241-7242

  Lee, Younghee ^a   Huang, He ^a   Sayre, Lawrence M ^a  

^a CASE WESTERN RESERVE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE OXIDASE (COPPER CONTAINING); PYRROLE DERIVATIVE;

ARTICLE; ENZYME BINDING; ENZYME INHIBITION; MODEL;

EID: 0029746176     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9543210     Document Type: Article

References (18)

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11. 11 that polyamines are metabolized at primary and not secondary amine positions.
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13. 2 m/z 235.1573; found 235.1579 (56.7%). The major side product in the case of 1b was identified, following isolation, as that arising from electrophilic substitution of 1-pyrroline at C-2 of 6b, 2-(pyrrolidin-2-yl)-4-(pyrrolidin-1-yl)-6-tert-butylresorcinol.
14. 3 reaction of 2a with 4,4-diethoxybutanamine.
15. 2 m/z 231.1260; found 231.1260 (88.7%).
16. 2 occurred in 20 min using 10 mM benzylamine.
17. 3-Phenyl-3-pyrroline was prepared by addition of PhMgBr to N-(carboethoxy)-3-pyrrolidone, N-deprotection of the resulting phenyl carbinol by refluxing overnight in 1:1 n-propanol aqueous KOH (10 N), and finally dehydration by refluxing in concd HCl for 1 h. The compound has also been prepared from 2-phenyl-2-vinylaziridine: Hortmann, A. G.; Koo, J.-y. J. Org. Chem. 1974, 39, 3781.
18. Silverman, R. B. Mechanism-Based Enzyme Inactivation: Chemistry and Enzymology; CRC Press, Inc.: Boca Raton, FL, 1988; pp 3-30.