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Paper | Regular issue | Vol 32, No. 9, 1991, pp.1821-1830
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5818
Metabolic Formation and Chemical Synthesis of 5,6-Cyclopenteno-4,11-dihydro-3H-pyrido[3,2-a]carbazol-3-one, the Major Intestinal Bacterial Metabolite of the Pyrolysis Mutagen 5,6-Cyclopenteno-11H-pyrido[3,2-a]carbazole (LYS-P-1)

David G. I. Kingston,* Yue-Zhong Shu, Roger L. Van Tassell, and Tracy D. Wilkins

*Department of Chemisry, Virginia Polytecnic Institute and State University, Blacksburg, Virginia 24061-0212, U.S.A.


Anaerobic incubation of the lysine pyrolysis mutagen 5,6-cyclopenteno-11H-pyrido[3,2-a]carbazole (Lys-P-1, 3) with human intestinal bacterial mixtures yielded the major metabolite 5,6-cyclopenteno-4,11-dihydro-3H-pyrido[3,2-a]carbazol-3-one (3-HO-Lys-P-1, 4). The metabolite (4) has been synthesized from 4-aminoindane in six steps. NAD and NADP significantly enhanced the metabolism, suggesting that the transformation of of 3 leading to 4 involves a hydration and subsequent dehydrogenation processes.