Ein tricyclisches Polyamid als Rezeptor für Kohlenhydrate in organischen Medien

Abstract

Glucose in Chloroform gelöst – der Rezeptor 1 macht es möglich! Zwei Biphenyl‐Einheiten und acht Carbonsäureamidbrücken bilden in 1 einen zur β‐Glucopyranosyl‐Einheit komplementären Hohlraum. Selbst in Gegenwart von Methanol als Cosolvens bindet 1 Octylglycoside mit ungewöhnlich hoher Affinität und Stereoselektivität.

Flexible Synthetic Carbohydrate Receptors as Inhibitors of Viral Attachment

“…The structures of noncovalent SCRs include calixarenes and oligoaromatic receptors, ,− cyclodextrins, ,− porphyrin conjugates, podand receptors, ,,,,,,,,,,− peptide-based receptors, , cholaphanes, and the encapsulating temple receptors. ,,,,,,,,,− Although several reviews of noncovalent SCRs exist, − ,, the field continues to develop rapidly and a few key examples are highlighted below to discuss the design of noncovalent SCRs (Figure ) and their evolution as antivirals.…”

“…Other temples prepared by the Davis group bind all manner of glucosides and other “all-equatorial” glycan derivatives, such as chitobiose, cellobiose, ,, and maltoside, where all of the hydroxyl groups are positioned equatorially around the pyranoside scaffold. Important achievements that have resulted from these efforts include new temple receptors that bound to octyloxy glucosides with K a s as high as 3.0 × 10 5 M –1 in CDCl 3 ,,− ,, and 1.2 × 10 4 M –1 in aqueous solutions . Water solubility is achieved by appending dendritic groups to the temple, and different lengths and degrees of flexibility of the aromatic planar sections can be modulated to accommodate glucoside oligomers of different lengths. ,,, The polar aromatic pillars are sufficiently rigid to prevent the collapse of the apolar aromatic surfaces in water .…”