1209481-45-7Relevant academic research and scientific papers
Chiral diaminopyrrolic receptors for selective recognition of mannosides, Part 1: Design, synthesis, and affinities of second-generation tripodal receptors
Nativi, Cristina,Francesconi, Oscar,Gabrielli, Gabriele,Vacca, Alberto,Roelens, Stefano
, p. 4814 - 4820 (2011/05/15)
A new generation of chiral tripodal receptors for recognition of carbohydrates, featuring trans-1,2-diaminocyclohexane as a key structural element, and their recognition properties toward a set of glycosides of biologically relevant monosaccharides is des
A chiral pyrrolic tripodal receptor enantioselectively recognizes β-mannose and β-mannosides
Arda, Ana,Vnturi, Chiara,Nativi, Cristina,Francesconi, Oscar,Gabrielli, Gabriele,Javier Canada,Jimenez-Barbero, Jesus,Roelens, Stefano
supporting information; experimental part, p. 414 - 418 (2010/06/13)
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.
