Substrate control through per-O-methylation of cyclodextrin acids.
Per-O-methylated cyclodextrins containing a single 2-O-(2-acetate), 2-O-(3-propanoate) or a 6-carboxylate were investigated for glycosidase activity on p-nitrophenyl glycosides. The former two compounds displayed enzyme catalysis giving rate accelerations of 500-1000, while the latter compound gave marginal catalysis. These results show that per-O-methylated cyclodextrins direct substrate binding from the secondary face leading to better catalysis.
Fenger
Thomas H
TH
Department of Chemistry, University of Copenhagen, Universitetsparken 5, 2100 Kbh Ø, Denmark.
Bols
Mikael
M
D002264:Carboxylic Acids / Q000737:chemistry*; D003505:Cyclodextrins / Q000737:chemistry*; D007700:Kinetics; D008745:Methylation; D010100:Oxygen / Q000737:chemistry*; D013379:Substrate Specificity
D002264:Carboxylic Acids; D003505:Cyclodextrins; D010100:Oxygen