http://www.cnr.it/ontology/cnr/individuo/prodotto/ID299868

Systematic dissection of an aminopyrrolic cage receptor for ?-glucopyranosides reveals the essentials for effective recognition (Articolo in rivista)

Type

Prodotto della ricerca (Classe)
Articolo in rivista (Classe)

Label

Systematic dissection of an aminopyrrolic cage receptor for ?-glucopyranosides reveals the essentials for effective recognition (Articolo in rivista) (literal)

Anno

2014-01-01T00:00:00+01:00 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi

10.1002/chem.201400365 (literal)

Alternative label

Francesconi O.; Gentili M.; Nativi C.; Arda A.; Canada F.J.; Jimenez-Barbero J.; Roelens S. (2014)
Systematic dissection of an aminopyrrolic cage receptor for ?-glucopyranosides reveals the essentials for effective recognition
in Chemistry (Weinh., Print)
(literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori

Francesconi O.; Gentili M.; Nativi C.; Arda A.; Canada F.J.; Jimenez-Barbero J.; Roelens S. (literal)

Pagina inizio

6081 (literal)

Pagina fine

6091 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#url

http://www.scopus.com/inward/record.url?eid=2-s2.0-84900035293&partnerID=q2rCbXpz (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume

20 (literal)

Rivista

Chemistry (Rivista)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#pagineTotali

11 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroFascicolo

20 (literal)

Note

Scopu (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni

Istituto di Metodologie Chimiche (IMC), Consiglio Nazionale Delle Ricerche (CNR), Dipartimento di Chimica, 50019 Sesto Fiorentino, Firenze, Italy; Dipartimento di Chimica, Università di Firenze, Polo Scientifico e Tecnologico, 50019 Sesto Fiorentino, Firenze, Italy; Centro Risonanze Magnetiche (CERM), Polo Scientifico e Tecnologico, 50019 Sesto Fiorentino, Firenze, Italy; Chemical and Physical Biology, Centro de Investigaciones Biolõgicas, CSIC, Ramiro de Maeztu 9, 28040 Madrid, Spain (literal)

Titolo

Systematic dissection of an aminopyrrolic cage receptor for ?-glucopyranosides reveals the essentials for effective recognition (literal)

Abstract

A set of structures designed for the recognition of glucosides has been obtained by systematically destructuring a tripodal aminopyrrolic cage receptor that selectively recognizes octyl-?-D-glucopyranoside (Oct?Glc). NMR spectroscopy and isothermal titration calorimetry binding measurements showed that cleavage of one pillar of the cage was beneficial to the binding properties of the receptor, as long as two residual amino groups of the cleaved pillar were present. Removal of these two residual amino groups produced a dramatic loss of affinity for Oct?Glc of the resulting monocyclic analogue of the parent cage receptor. A significant improvement in the binding ability was achieved by replacing one pillar with two aminopyrrolic hydrogen-bonding arms, despite the loss of a preorganized structure. In contrast to the cage receptor, recognition of Oct?Glc was observed, even in a competitive medium (30% DMF in chloroform). Structural studies in solution, carried out through NMR spectroscopy and molecular modeling calculations, led to the elucidation of the 3D binding modes of the side-armed monocyclic receptors; this highlighted the key role of the amino groups and demonstrated the occurrence of a rotaxane-like complex, which featured the octyl chain of the glucoside threaded through the macrocyclic ring. Comfort is paramount! A set of structures designed for the recognition of glucosides has been obtained by systematically destructuring a tripodal aminopyrrolic cage receptor. A ?-glucoside is more effectively recognized by an adaptive cleft than by a preorganized cage, if a more comfortable fit can be achieved (see picture). © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. (literal)

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