Pyrrolic tripodal receptors effectively recognizing monosaccharides. Affinity assessment through a generalized...

Area of Science:

• Supramolecular Chemistry
• Carbohydrate Chemistry
• Organic Synthesis

Background:

• Developing synthetic receptors for selective carbohydrate recognition is crucial for biological and medical applications.
• Hydrogen bonding interactions are key to designing effective molecular recognition systems.

Purpose of the Study:

• To design and synthesize novel tripodal receptors for the molecular recognition of carbohydrates.
• To investigate the binding affinities and selectivities of these receptors for biologically relevant monosaccharides.

Main Methods:

• Synthesis of benzene-based tripodal receptors incorporating pyrrolic and imino/amino H-bonding ligands.
• NMR titrations in CDCl3 and CD3CN to determine binding affinities (micromolar to millimolar).
• Isothermal Titration Calorimetry (ITC) and collision-induced dissociation (CID) experiments to analyze binding thermodynamics and gas-phase selectivity.

Main Results:

• Receptors 3 and 4 demonstrated effective binding of octylglycosides of glucose, galactose, mannose, and N-acetyl-glucosamine.
• Both receptors showed high selectivity for glucose, with receptor 3 exhibiting up to 250-fold selectivity.
• Hydrogen bonding from imino/amino and pyrrolic groups significantly contributed to carbohydrate binding, as evidenced by ITC and crystallographic data.

Conclusions:

• The developed tripodal receptors represent a new generation for carbohydrate molecular recognition.
• The study highlights the importance of specific H-bonding groups (imino/amino, pyrrolic) for effective binding and selectivity.
• The findings pave the way for designing advanced H-bonding receptors tailored for specific carbohydrate targets.