Chemical Degradation of Dipicolinic Acid-C14 and Its Application in Biosynthesis by Penicillium citreo-viride

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Kanie, Matuso (Kagoshima University, Kagoshima, Japan), Shigeo Fujimoto, and J. W. Foster. Chemical degradation of dipicolinic acid-C14 and its application to biosynthesis by Penicillium citreo-viride. J. Bacteriol. 91:570–577. 1966.—A chemical degradation of dipicolinic acid-C14 has been worked out, enabling determination of the specific radioactivity of the carboxyl-carbons (carbons-7 and -8), and of the following carbons of the pyridine ring: carbons-2 and -6 combined, carbons-3 and -5 combined, and carbon-4. The degradation was applied to dipicolinic acid synthesized by washed, submerged mycelium of the mold from glucose and C14O2, and from glucose-1-C14, -2-C14, and -6-C14. The distribution of radioactivity within the labeled dipicolinic acids is consistent with operation of respiratory cycles and with the incorporation of one molecule of CO2 in the pyridine acid. A C3 compound is a primary building block. The C7 chain is believed to result from a C3 plus C4 condensation, pyruvic acid and aspartic acid β-semialdehyde being proposed as likely precursors. Other aspects of the biosynthesis of C7 open-chain compounds and of dipicolinic acid are discussed.

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