Spectroscopic anatomy of molecular-imprinting of cyclodextrin. Evidence for preferential formation of ordered cyclodextrin assemblies.
The processes of molecular-imprinting of beta-cyclodextrin (beta-CyD) with cholesterol and stigmasterol (cross-linking agent = diisocyanate) have been analyzed by matrix-assisted laser desorption/ionization time-of-flight mass spectroscopy. These templates enormously promote the formation of dimers and trimers of beta-CyD, which are only inefficiently formed in their absence. These ordered assemblies are the guest-binding sites, in which two or three beta-CyD molecules cooperate to bind large steroids. Ordered assemblies are also formed when 2,6-di-O-methyl-beta-cyclodextrin is used in place of beta-CyD. Direct spectroscopic evidence for molecular-imprinting effect has been obtained. Molecular imprinting of CyDs is potent for tailor-made preparation of synthetic receptors for nanometer-scaled guests.
Hishiya
Takayuki
T
Research Center for Advanced Science and Technology, The University of Tokyo, 4-6-1 Komaba, Tokyo 153-8904, Japan.
Asanuma
Hiroyuki
H
Komiyama
Makoto
M
D002784:Cholesterol / Q000737:chemistry*; D003432:Cross-Linking Reagents / Q000737:chemistry; D003485:Cyanates / Q000737:chemistry; D003505:Cyclodextrins / Q000737:chemistry*; D017953:Isocyanates; D009682:Magnetic Resonance Spectroscopy; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D013265:Stigmasterol / Q000737:chemistry*; D013698:Templates, Genetic; D014051:Toluene 2,4-Diisocyanate / Q000737:chemistry; D047392:beta-Cyclodextrins
D003432:Cross-Linking Reagents; D003485:Cyanates; D003505:Cyclodextrins; D017953:Isocyanates; D047392:beta-Cyclodextrins; C015262:1,6-hexamethylene diisocyanate; D014051:Toluene 2,4-Diisocyanate; D002784:Cholesterol; D013265:Stigmasterol; C031215:betadex