title: Access to Versatile β-Cyclodextrin Scaffolds through Guest-Mediated Monoacylation.
abstract: Herein, we report the selective mono-derivatization of heptakis[6-deoxy-6-(2-aminoethylsulfanyl)]-β-CD (1) through a guest-mediated covalent capture strategy. The use of guests functionalized with cleavable linkers enables the installation of an amine-orthogonal thiol group on the primary rim of 1 as a handle for further transformations to the β-CD scaffold. Applying this methodology, two novel monoderivatized β-CDs were obtained in good yield and high purity. Both of these monoacylated CDs were amenable to facile linker cleavage and further modification at the resulting thiol group. This methodology can be applied towards the synthesis heterofunctionalized β-CD constructs for analyte sensing, drug delivery, and other applications.
authors.affiliation: Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada.
authors.forename: Nesrin
authors.initials: N
authors.lastname: Vurgun
authors.affiliation: Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada.
authors.forename: Rodolfo F
authors.initials: RF
authors.lastname: Gómez-Biagi
authors.affiliation: Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada. mnitz@chem.utoronto.ca.
authors.forename: Mark
authors.initials: M
authors.lastname: Nitz
mesh_terms: D000215:Acylation; D003505:Cyclodextrins / Q000138:chemical synthesis* / Q000737:chemistry*; D016503:Drug Delivery Systems / Q000379:methods*; D015394:Molecular Structure; D047392:beta-Cyclodextrins / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D003505:Cyclodextrins; D047392:beta-Cyclodextrins; C000608472:heptakis(6-deoxy-6-(2-aminoethylsulfanyl))-beta-cyclodextrin
keywords: covalent capture; cyclodextrin; host-guest systems; selective functionalization