A NOVEL SYNTHESIS OF SUBSTITUTED IMIDAZOLES, AND A REEXAMINATION OF A PURPORTED CHYMOTRYPSIN MODEL

Article abstract of DOI:10.1016/S0040-4039(00)99358-4

Rearrangement of an N-hydroxyimidazole to a side-chain functionalized derivative permits easy synthesis of a puported chymotrypsin mimic that contains a "catalytic triad" as part of a cyclodextrin molecule.Contrary to the previous claims, the added functional groups do not play a role in the cyclodextrin reaction with a typical substrate, but in fact slow the reaction because of steric hindrance.