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Phytochemical Studies on the Tobacco Alkaloids. XII. Identification of -Methylaminobutyraldehyde and its Precursor Role in Nicotine Biosynthesis

^a Division of Plant Biochemistry, Central Research Institute, Japan Monopoly Corporation, 1-28-3, Nishishinagawa, Shinagawa-ku, Tokyo, Japan

-Methylaminobutyraldehyde (N-methylpyrroline) labeled with ¹⁴C was isolated from tobacco roots which had metabolized ornithine-2-¹⁴C. It was labeled most strongly 4 hours after adding ornithine-2-¹⁴C to the root, also labeled by putrescine-1,4-¹⁴C and methionine-¹⁴CH₃, and observed in the root but not in the aerial portions of tobacco plants. -Methyl-aminobutyraldehyde when added back to the root was an efficient precursor of nicotine. Identity of -methylaminobutyraldehyde from tobacco roots was confirmed by comparison with the authentic compound.

The existence of -methylaminobutyraldehyde (N-methylpyrroline) in the biosynthetic pathway of nicotine indicates that the methyl group must be introduced before condensation of the pyridine moiety with the pyrrolidine moiety.

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