The neurotransmitter epinephrine, also known as adrenaline,…
The neurotransmitter epinephrine, also known as adrenaline, is involved in regulating visceral functions (e.g., respiration) and plays an important role in the fight-or-flight response in many animals. Consider the structure of N-protonated epinephrine (shown below) and answer the following questions. The lowest-energy conformation of N-protonated epinephrine is stabilized by hydrogen bonding between the hydroxyl and the ammonium group. Which of the following Newman projections (A-F) represents this conformation viewed through the C1-C2 bond? Recall that dihedral angles are measured clockwise when answering the next two questions. Consider the conformation of N-protonated epinephrine in which the aryl (Ar) substituent and the ammonium group are eclipsed. What is the dihedral angle between hydroxyl group and ammonium group in this conformation? What is the dihedral angle between the aryl (Ar) substituent and the ammonium group in Newman structure B? Do Newman structures A and C represent conformational isomers?