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Studies on the biosynthesis of the pyrrolidine ring of nicotine



Studies on the biosynthesis of the pyrrolidine ring of nicotine



Biochemistry 4(8): 1628-1632



A degradation of nicotine which resulted in fission of the pyrrolidine ring to yield oxalic acid, methylamine, and 3-pyridyl methyl ketone was developed, which, along with previously utilized degradations, permitted assessment of C14 in each carbon of the ring. After a biosynthetic period of 2 days with [2-Cl4]acetate, radioactivity was found to be evenly distributed between positions 2 and 5, and also between positions 3 and 4, but the quantity of Cl4 in positions 3 and 4 was almost twice as great as that in positions 2 and 5. The labeling pattern was consistent with the hypothesis that acetate was converted by way of the tricarboxylic acid cycle to glutamate which proceeded through a symmetrical intermediate to form the pyrrolidine ring.

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Accession: 025572989

Download citation: RISBibTeXText

PMID: 5863326

DOI: 10.1021/bi00884a026


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The biosynthesis of the pyrrolidine ring of nicotine. Biochimica et Biophysica Acta 18(1): 141-142, 1955

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