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Title: Stereochemical Preference of 2'-Deoxycytidine for Chiral Bis(diamido)-bridged Basket Resorcin[4]arenes
Authors: Ilaria, D'Acquarica
Andrea, Calcaterra
Fabiola, Sacco
Federica, Balzano
Federica, Aiello
Tafi, Andrea 
Nicolò, Pesci
Gloria Uccello, Barretta
Bruno, Botta
Issue Date: 2013
Project: None 
Bis(diamido)-bridged basket resorcin[4]arene and its enantiomer proved able to interact with 2'-deoxycytidine () and pyrimidine nucleoside analogs in dimethyl sulfoxide (DMSO) solution. In such a solvent, the resorcinarene hosts adopt a preferential 1,3-alternate-like conformation, with a larger cavity delimited by two syn 3,5-dimethoxyphenyl moieties, and two external pockets, each delimited by the other 3,5-dimethoxyphenyl group and its diamido arm (the wing). Complexation phenomena were investigated by nuclear magnetic resonance (NMR) methods, including 1 H NMR DOSY and 1D ROESY experiments, and molecular modeling. Heteroassociation constants of [] and [] diastereoisomeric complexes were obtained from diffusion data by single point measurements, and from nonlinear fitting of 1 H NMR chemical shifts. Selective proton relaxation rate measurements allowed us to significantly discriminate the two complexes by identifying two different interaction sites of the guest in the resorcin[4]arene host, depending on its configuration.
ISSN: 0899-0042
DOI: 10.1002/chir.22224
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