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Glutamate as a precursor for the pyrrolidine ring of nicotine



Glutamate as a precursor for the pyrrolidine ring of nicotine



Journal of Biological Chemistry 233(4): 939-943



Nicotiana rustica plants that had been fed glutamic acid-2-C14 synthesized radioactive nicotine. A degradation of the radioactive nicotine, which permitted isolation of carbon 2 of the pyrrolidine ring, demonstrated that this C atom contained about 45% of the original radioactivity of the nicotine. The pyridine ring was shown to contain about 10% and carbons 3, 4, or 5 of the pyrrolidine ring contained the remaining 45% of the original radioactivity of the nicotine. A procedure was developed for the degradation of the nicotine molecule, employing well established reactions, which permitted isolation of the C atom from position 5 of the pyrrolidine ring. The residual C skeleton of the molecule was recovered as a derivative of a substituted aliphatic primary amine. The intermediates produced at each step of this degradation were isolated. Radioactive nicotine, obtained from plants fed glutamic acid-2-Cl4, was degraded by this procedure. Half of the C14 of the nicotine was associated with C 5 of the pyrrolidine ring. The remaining radioactivity was shown to be present in the amine derivative and, from the previous degradation, was known to be located primarily in the C which was originally at position 2 of the pyrrolidine ring of nicotine. The pattern of labeling of nicotine from plants administered glutamic acid-2-C14 supports the postulation of a symmetrical intermediate along the pathway of incorporation of the amino acid into the pyrrolidine ring.

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Accession: 014061708

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PMID: 13587520


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