Chorismate mutase inhibitors transition state analogs

Adamantane has an extra methylene bridge (the asterisk in the diagram) linked to the six-membered ring, thus stabilizing a cagelike structure. The authors indeed subsequently showed that some adamantane derivatives are potent inhibitors of chorismate mutase thus, these are examples of transition-state analogs. 

Bartlett, P.A., Nakagawa, Y., Johnson, C.R., Reich, S. and Luis, A. (1988) Chorismate Mutase Inhibitors Synthesis and Evaluation of Some Potential Transition State Analogs, J. Org. Chem., 53, 3195-3210. 

It has been shown that both the catalyzed and the uncatalyzed reaction proceed through a chairlike transition state, stabilized in polar media59 60-143 262-263. Compound 1, an analog of the transition-state structure, proved to be a potent inhibitor of E. coli chorismate mutase-prephenate dehydrogenase204-255. For a discussion of the mechanism and structural requirements of the enzyme see refs 266 and 267. 

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