The prototype of a new family of chiral receptors based on a tripodal scaffold and featuring pyrrolic binding arms containing the trans-1,2- diaminocyclohexane motif, was reported. A cage endowed with a somewhat enlarged cavity was designed, in the belief that fine-tuning of the cage size would lead to a significantly improved affinity even in more polar media. Reaction of the trialdehyde 4 with the mono-BOC-protected diamine 2, followed by reduction of the resulting Schiff base and subsequent deprotection of the amino groups, yielded the tripodal hexaamine 5, which was condensed with pyrrole-2,5- dicarbaldehyde under the conditions used for preparing the bicyclic receptor 1. A preliminary screening indicated that, while Glc, Gal, and GlcNAc were moderately bound, strong recognition occurred with mannosides. βMannose was also extracted in benzene, though to a lesser extent (10%), and αMannose could not be detected.

A Chiral Pyrrolic Tripodal Receptor Enantioselectively Recognizes beta-Mannose and beta-Mannosides / Ardà, A.; Venturi, C.; Nativi, C.; Francesconi, O.; Gabrielli, G.; Canada F. X.; Jimenez-Barbero, J.; Roelens, S.;. - In: CHEMISTRY-A EUROPEAN JOURNAL. - ISSN 0947-6539. - STAMPA. - 16:(2010), pp. 414-418.

A Chiral Pyrrolic Tripodal Receptor Enantioselectively Recognizes beta-Mannose and beta-Mannosides

VENTURI, CHIARA;NATIVI, CRISTINA;FRANCESCONI, OSCAR;GABRIELLI, GABRIELE;ROELENS, STEFANO
2010

Abstract

The prototype of a new family of chiral receptors based on a tripodal scaffold and featuring pyrrolic binding arms containing the trans-1,2- diaminocyclohexane motif, was reported. A cage endowed with a somewhat enlarged cavity was designed, in the belief that fine-tuning of the cage size would lead to a significantly improved affinity even in more polar media. Reaction of the trialdehyde 4 with the mono-BOC-protected diamine 2, followed by reduction of the resulting Schiff base and subsequent deprotection of the amino groups, yielded the tripodal hexaamine 5, which was condensed with pyrrole-2,5- dicarbaldehyde under the conditions used for preparing the bicyclic receptor 1. A preliminary screening indicated that, while Glc, Gal, and GlcNAc were moderately bound, strong recognition occurred with mannosides. βMannose was also extracted in benzene, though to a lesser extent (10%), and αMannose could not be detected.
16
414
418
Ardà, A.; Venturi, C.; Nativi, C.; Francesconi, O.; Gabrielli, G.; Canada F. X.; Jimenez-Barbero, J.; Roelens, S.;
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2158/406393
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