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.

Stereochemical Preference of 2'-​Deoxycytidine for Chiral Bis(diamido)​-​bridged Basket Resorcin[4]​arenes / D'Acquarica, Ilaria; Calcaterra, Andrea; Sacco, F.; Balzano, F.; Aiello, F.; Tafi, A.; Pesci N., Uccello Barretta G.; Botta, Bruno. - In: CHIRALITY. - ISSN 1520-636X. - STAMPA. - 25:(2013), pp. 840-851. [10.1002/chir.22224]

Stereochemical Preference of 2'-​Deoxycytidine for Chiral Bis(diamido)​-​bridged Basket Resorcin[4]​arenes

D'ACQUARICA, Ilaria;CALCATERRA, ANDREA;BOTTA, Bruno
2013

Abstract

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.
2013
Chiral basket resorcin[4]arenes, encapsulation phenomena, nuclear magnetic resonance, pyrimidine nucleoside analogues, supramolecular chemistry
01 Pubblicazione su rivista::01a Articolo in rivista
Stereochemical Preference of 2'-​Deoxycytidine for Chiral Bis(diamido)​-​bridged Basket Resorcin[4]​arenes / D'Acquarica, Ilaria; Calcaterra, Andrea; Sacco, F.; Balzano, F.; Aiello, F.; Tafi, A.; Pesci N., Uccello Barretta G.; Botta, Bruno. - In: CHIRALITY. - ISSN 1520-636X. - STAMPA. - 25:(2013), pp. 840-851. [10.1002/chir.22224]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/525648
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