Synthetic Organic Chemistry and the Shikimate Pathway: Inhibitors and Intermediates
Scientists have been interested in the shikimate pathway (Fig. 1) for decades, yet it shows no sign of losing this popularity.1,2 Part of the reason for this is that it offers something for everyone. Until quite recently a number of the key intermediates in the sequence had never been synthesized non-enzymatically. The unusual mechanisms of several of the enzymes involved have still not been fully elucidated. And the search for inhibitors of the various steps continues to be spurred by the success of glyphosate as an herbicide.
KeywordsShikimic Acid Shikimate Pathway Allylic Bromide Allylic Alcohol Chorismate Mutase
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- 1.HASLAM, E. 1974. The Shikimate Pathway. Wiley-Interscience, New York.Google Scholar
- 3.For a review of early syntheses of shikimate, see Reference 2. For more recent syntheses, see References 4 and 5 and references cited therein.Google Scholar
- 6.DANISHEFSKY, S., M. HIRAMA, N. FRITSCH, J. CLARDY. 1979. Synthesis of disodium prephenate and disodium epiprephenate. Stereochemistry of prephenic acid and an observation on the base-catalyzed rearrangement of prephenic acid to p-hydroxyphenyllactic acid. J. Amer. Chem. Soc. 101: 7013–7018.CrossRefGoogle Scholar
- 7.GRAMLICH, W., H. PLIENINGER. 1979. Total synthesis of disodium prephenate. II. Synthesis and stereochemical assignment of disodium prephenate. Chem. Ber. 112: 1571–1584. For a recent synthesis of prephenate, see: Ramage, R., A.M. Macleod. 1984. J. Chem. Soc. Chem. Commun. 1008–1010.CrossRefGoogle Scholar
- 10.MCKENNA, C.E., J. SCHMIDHAUSER. 1979. Functional selectivity in phosphate ester dealkylation with bromotrimethylsilane. J. Chem. Soc. Chem. Commun. 739.Google Scholar
- 11.UHLMANN, E., W. PFLEIDERER. 1980. New improvement in oligonucleotide synthesis by use of the p-nitro-phenylethyl phosphate blocking group and its deprotection by DBU or DBN. Tetrahedron Lett. 1181–1184.Google Scholar
- 12.OVERMAN, L.E., F.M. KNOLL. 1979. Palladium(II)-catalyzed rearrangement of allylic acetates. Tetrahedron Lett. 321–324.Google Scholar
- 16.DAVIS, B.D., E.S. MINGIOLI. 1953. Aromatic biosynthesis. VII. Accumulation of two derivatives of shikimic acid by bacterial mutants. J. Bacteriol. 66: 129–136.Google Scholar
- 17.KHORANA, H.G., A.R. TODD. 1953. Studies on phosphorylation. XI. The reaction between carbodiimides and acid esters of phosphoric acid. A new method for the preparation of pyrophosphates. J. Chem. Soc. 2257–2260.Google Scholar
- 29.FLEET, G.W.J., P.J. HARDING. 1979. Convenient synthesis of bis(triphenylphosphine)-copper(I) tetrahydroborate and reduction of acid chlorides to aldehydes. Tetrahedron Lett. 975–978.Google Scholar
- 30.EVANS, D.A., L.K. TRUESDALE. 1973. Cyanosilylation of aldehydes and ketones. A convenient route to cyanohydrin derivatives. J. Chem. Soc. Chem. Commun. 55–56.Google Scholar