Selective mono-O-sulfonylation of A,B-di-altro- β-cyclodextrin by utilizing restricted orientation of a guest-type sulfonylating reactant in the elliptically distorted cavity: the 2-O- and 3-O-2-naphthalenesulfonates as a versatile scaffold to prepare artificial enzymes with controlling substrate orientation

A,B-di-altro-β-cyclodextrin, which has 21 different hydroxyl groups, was selectively sulfonylated by 2-naphthalenesulfonyl chloride at the 2^A-OH of the altrose residue and the 3^G-OH of the glucoside residue adjacent to the altroside residue. The latter sulfonate provides for the first time a possibility for the synthesis of functional cyclodextrins that have two altrose residues adjacent to the functionalized one (either of glucose type or of altrose type) to control the orientation of substrate.