2217. Chorismic Acid
Nomenclature
Description and references
The first branch point intermediate in the biosynthesis of aromatic amino acids via the shikimate pathway in bacteria, fungi, and higher plants; naturally occurring as the (-)-form. Its existence was predicted, then discovered during development of a mutant of A. aerogenes: M. I. Gibson et al., Nature 195, 1173 (1962); M. I. Gibson, F. Gibson, Biochim. Biophys. Acta 65, 160 (1962). NMR and preliminary structure study: F. Gibson, M. Jackman, Nature 198, 388 (1963). Isoln and metabolism study: M. Gibson, F. Gibson, Biochem. J. 90, 248 (1964). Prepn and characterization of the barium salt: F. Gibson, ibid. 256. Structure, relative and abs config, prepn of the monohydrate: J. M. Edwards, L. M. Jackman, Aust. J. Chem. 18, 1227 (1965). Total synthesis of racemic chorismic acid: D. A. McGowan, G. A. Berchtold, J. Am. Chem. Soc. 104, 1153 (1982); B. Ganem et al., ibid. 6787; improved synthesis: G. A. Berchtold et al., ibid. 105, 6265 (1983); short formal synthesis: G. H. Posner et al., J. Org. Chem. 52, 4836 (1987). Total synthesis of (-)-form: J. L. Pawlak, G. A. Berchtold, ibid. 1765. Potential use in development of herbicides: S. Stinson, Chem. Eng. News 60, 31 (Dec. 6, 1982). Reviews of chorismic acid in biosynthesis of aromatic amino acids: F. Gibson, J. Pittard, Bacteriol. Rev. 32, 465-492 (1968); R. J. Ife et al., J. Chem. Soc. Perkin Trans. 1 1976, 1776-1783; U. Weiss, J. M. Edwards, The Biosynthesis of Organic Compounds (Wiley, New York, 1980) pp 134-143. See also shikimic acid.
