Solid-phase SN2 macrocyclization reactions to form beta-turn mimics.
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[formula: see text] Efficient solid-phase SN2 macrocyclization reactions were sought to facilitate preparations of focused libraries of beta-turn mimetics. A very efficient, but undesired, cyclization reaction to give five-membered ring lactams 4 was identified in attempts to use O-nucleophiles. Subsequent studies focused exclusively on S-nucleophiles. These reactions gave the desired macrocyclization products 1 in high purities and good overall yields. Conformational analyses of illustrative macrocyclization products 1 via NMR, CD, and molecular simulations showed that they seem to sample both type I and type II beta-turn conformations in solution. CD studies indicate a curious relationship between the preferred conformation and the amino acids encapsulated in the macrocycles.
author list (cited authors)
Feng, Y., Pattarawarapan, M., Wang, Z., & Burgess, K.
complete list of authors
Feng, Y||Pattarawarapan, M||Wang, Z||Burgess, K