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Conformationally restricted P1-P1' transition state analogues. Synthesis of 1(R), 3(R) [1(S), 2(S)] and 1(S), 3(S) [1(S), 2(S)] 3-[3-cyclohexyl-2-[(BOC)amino]-1-hydroxypropyl]-2,2-dimethylcyclo propane carboxylic acids

✍ Scribed by Michael J. Melnick; Sharon N. Bisaha; Ronald B. Gammill

Publisher
Elsevier Science
Year
1990
Tongue
French
Weight
256 KB
Volume
31
Category
Article
ISSN
0040-4039

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✦ Synopsis

A concise synthesis and determination of absolute stereochemistry of two novel diastereomeric cyclopropyl containing transition state mimics isdescribed. A major advance in the development of renin inhibitors was the replacement of the scissile bond (PI-PI') with "transition state mimics" such as statinel (1) and Leu[CH(OH)CH&/alWJ (2, LVA). Thisstrategy replaced the PI-Pl'dipeptide with a nonhydrolysable analogue which contained a j%hydroxyl group thought to mimic a proposed transition state (3) in the enzyme-substrate

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