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. 1968 Jan;43(1):93–98. doi: 10.1104/pp.43.1.93

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

Shigenobu Mizusaki a, Takuro Kisaki a,1, Einosuke Tamaki a
PMCID: PMC396017  PMID: 16656744

Abstract

γ-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. γ-Methyl-aminobutyraldehyde when added back to the root was an efficient precursor of nicotine. Identity of γ-methylaminobutyraldehyde from tobacco roots was confirmed by comparison with the authentic compound.

The existence of γ-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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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

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