New pH-triggered conformational switches based on trans-2-aminocyclohexanol moiety
Poster Number
17A
Research or Creativity Area
Natural Sciences
Abstract
The derivatives of trans-2-aminocyclohexanols with a proper configuration possess a negative allosteric cooperativity and can serve as powerful conformational pH-triggers. Their protonation leads to a conformational flip due to a strong intramolecular hydrogen bond. This ‘impulse’ is mechanically transmitted by the cycle to induce a conformational change of a remote site, thus altering its properties. Variation of the substituents allows a tuning of the conformational equilibrium. To further expand the variety of potential pH-triggers, we synthesized a series of bis-acyloxy-trans-2-aminocyclohexanols and evaluated their conformational equilibria by 1H NMR spectroscopy. These molecular triggers can be used in a design of pH-sensitive lipid vesicles for drug and gene delivery.
Purpose
To expand the variety of potential molecular triggers, we synthesized a series of bis-acyloxy-trans-2-aminocyclohexanols and evaluated their conformational equilibria by 1H NMR spectroscopy. These molecular triggers can be used in a design of pH-sensitive lipid vesicles for drug and gene delivery.
Results
To expand the variety of potential molecular triggers, we synthesized a series of bis-acyloxy-trans-2-aminocyclohexanols and evaluated their conformational equilibria by 1H NMR spectroscopy.
Significance
We prepared and studied the molecular triggers that can be used in a design of pH-sensitive lipid vesicles for drug and gene delivery.
Location
Don and Karen DeRosa University Center (DUC) Poster Hall
Start Date
27-4-2024 10:30 AM
End Date
27-4-2024 12:30 PM
New pH-triggered conformational switches based on trans-2-aminocyclohexanol moiety
Don and Karen DeRosa University Center (DUC) Poster Hall
The derivatives of trans-2-aminocyclohexanols with a proper configuration possess a negative allosteric cooperativity and can serve as powerful conformational pH-triggers. Their protonation leads to a conformational flip due to a strong intramolecular hydrogen bond. This ‘impulse’ is mechanically transmitted by the cycle to induce a conformational change of a remote site, thus altering its properties. Variation of the substituents allows a tuning of the conformational equilibrium. To further expand the variety of potential pH-triggers, we synthesized a series of bis-acyloxy-trans-2-aminocyclohexanols and evaluated their conformational equilibria by 1H NMR spectroscopy. These molecular triggers can be used in a design of pH-sensitive lipid vesicles for drug and gene delivery.
