Authors: Matsuishi T
, Shimada T
, Morihara K
Footprint catalysis 9. Molecular footprint catalytic cavities imprinted with chiral hydantoins - enantioselective hydantoinase mimics.
Publication date: 1994
Journal: Bulletin of the Chemical Society of Japan
Abstract: Imprinting using chiral 5-phenyhydantoins ((5R)- and (5S)-5-pheny- 2,4-imidazolinedione) as templates could mark chiral molecular footprint-like cavities on a silica (alumina) gel surface. These cavities displayed evident enantioselective catalyses in reactions of (R)- and (S)-N-carboxyphenylglycine anhydrides, and (R)- and (S)-5- phenylhydantoins with 2,4-dinitrophenolate, respectively. A proposed mechanism and temperature effects on catalysis suggested that the enantioselectivities depended on the binding step of the catalysis
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