Promoting helicity in carbohydrate-containing foldamers through long-range hydrogen bonds

Area of Science:

• Supramolecular Chemistry
• Carbohydrate Chemistry
• Chemical Sensing

Background:

• Carbohydrates play crucial roles in biological systems.
• Understanding carbohydrate structure and interactions is vital.
• Induction of helical structures by carbohydrates is a key phenomenon.

Purpose of the Study:

• To develop a sensor system for probing carbohydrate-induced helical structures.
• To investigate the role of long-range hydrogen bonds in helix formation.
• To study the effect of anion complexation on helix stability.

Main Methods:

• Design and synthesis of a C(2)-symmetric xylylene bis(thiourea) sensor.
• Formation of intermolecular complexes with carbohydrates and benzoate anion.
• Analysis of helix uncoiling dynamics and thermodynamics.

Main Results:

• The sensor system successfully detected carbohydrate-induced helical structures.
• Intermolecular complex formation with benzoate anion promoted helix uncoiling.
• The free energy of helix uncoiling was found to be directly related to helix stability.

Conclusions:

• The developed sensor provides a new method for studying carbohydrate helical structures.
• Anion binding can effectively modulate carbohydrate-based helical assemblies.
• This work offers insights into the thermodynamics of supramolecular helix formation.