Supramolecular Control for the Modular Synthesis of Pseudopeptidic Macrocycles through an Anion-Templated Reaction

Abstract

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Organogel–quantum dots hybrid materials displaying fluorescence sensitivity and structural stability towards nitric oxide

“…In this context, pseudopeptidic compounds are good receptors of anions due to the coordination properties of the amide groups [2,3]. For this purpose, the preorganization provided by macrocyclic structures is important, and the preparation of such structures from C 2 pseudopeptidic bis(amidoamines) has been investigated in detail in our research group [4][5][6][7]. Previous studies focused on compounds such as 1 (Scheme 1) [4].…”

Crystal Structure of the N-Benzyloxycarbonyl-alanyl-phenylalanyl-methyl Ester: The Importance of the H-Bonding Pattern

“…During our research on the supramolecular chemistry of simple pseudopeptidic compounds [18][19][20][21][22][23], we screened the crystallization conditions of several different N-protected dipeptide sequences. Thus, we observed that when the Z-AF-OH dipeptide was placed in a MeOH solution containing an excess of 12 N HCl, large crystals appeared after very long time (several months).…”

“…During our ongoing research program in the field of pseudopeptidic compounds [18,19], we became interested in the self-aggregation process of the molecules through non-covalent interactions [20][21][22]. Within this field, the peptidic sequence Z-AF-OH appeared as an interesting target for molecular recognition by synthetic pseudopeptidic macrocycles [23].…”

New cyclic phosphonium salts derived from the reaction of phosphine-aldehydes with acid

“…Anions are less often employed in template syntheses because of their undesirable features, which include a high solvation energy, a low charge to radius ratio and a high pH dependence. Several examples of anion-assisted formation of rotaxanes and similar macromolecules are found in the literature [12]. The only multi-component anionic template to our knowledge was reported by Rubio and coworkers [12] in the synthesis of macrocycles derived from amino acids.…”