Chemical degradation of dipicolinic acid-C14 and its application in biosynthesis by Penicillium citreo-viride.

Kanie, Matuso (Kagoshima University, Kagoshima, Japan), Shigeo Fujimoto, and J. W. Foster. Chemical degradation of dipicolinic acid-C(14) and its application to biosynthesis by Penicillium citreo-viride. J. Bacteriol. 91:570-577. 1966.-A chemical degradation of dipicolinic acid-C(14) 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 C(14)O(2), and from glucose-1-C(14), -2-C(14), and -6-C(14). The distribution of radioactivity within the labeled dipicolinic acids is consistent with operation of respiratory cycles and with the incorporation of one molecule of CO(2) in the pyridine acid. A C(3) compound is a primary building block. The C(7) chain is believed to result from a C(3) plus C(4) condensation, pyruvic acid and aspartic acid beta-semialdehyde being proposed as likely precursors. Other aspects of the biosynthesis of C(7) open-chain compounds and of dipicolinic acid are discussed.