8480. Shikimic Acid
Nomenclature
Description and references
Naturally occurring (-)-form is a major biosynthetic precursor of phenylalanine, tyrosine, and tryptophan and hence of the majority of plant alkaloids. It is also involved in the biosynthesis of lignin, q.v., flavonoids and other important aromatic compounds. Isoln from the fruit of the oriental plant Illicium religiosum Sieb. et Zucc., Magnoliaceae (called in Japanese shikimi-no-ki): J. F. Eykman, Rec. Trav. Chim. 4, 32 (1885); idem, Ber. 24, 1278 (1891). Structural study: H. O. L. Fischer, G. Dangshat, Helv. Chim. Acta 17, 1200 (1934). Configuration: eidem, ibid. 18, 1206 (1935); 20, 705 (1937). Conformation in soln: L. D. Hall, J. Org. Chem. 29, 297 (1964). Enzymatic synthesis: P. R. Srinivasan et al., J. Am. Chem. Soc. 77, 4943 (1955). Stereospecific synthesis: R. McCrindle et al., J. Chem. Soc. 1960, 1560; E. E. Smissman et al., J. Am. Chem. Soc. 84, 1040 (1962). Improved synthesis: J. L. Pawlak, G. A. Berchtold, J. Org. Chem. 52, 1765 (1987). Synthesis of the (±)-form: R. Grewe, I. Hinrichs, Ber. 97, 443 (1964); R. Grewe, S. Kersten, Angew. Chem. 77, 859 (1965). Carcinogenicity study: I. A. Evans, M. A. Osman, Nature 250, 348 (1974). Reviews: B. A. Bohm, Chem. Rev. 65, 435-466 (1965); B. Ganem, Tetrahedron 34, 3353-3383 (1978); J. B. Harborne, Biosynthesis 6, 40-75 (1980). Books: E. Haslam, The Shikimate Pathway (Halsted Press, New York, 1974) 316 pp; idem, “Shikimic Acid Metabolites” in Comprehensive Organic Chemistry vol. 5 (Pergamon Press, Oxford, 1979) pp 1167-1205; U. Weiss, J. M. Edwards, The Biosynthesis of Organic Compounds (Wiley, New York, 1980) 728 pp.
