Consider the structure of the immunosuppressant FK-506, a molecule shown to disrupt calc...

Consider the structure of the immunosuppressant FK-506, a molecule shown to disrupt calcineurinmediated signal transduction in T-lymphocytes.

(a) What is the molecular formula of this immunosuppressant? (Chapter 1)

(b) How many stereocenters are present in FK-506? Determine the maximum number of stereoisomers possible.

(c) Identify and label the various functional groups present. (Chapter 1)

(d) Consider the two carbons in this structure labeled with asterisks (*). Determine the absolute configuration of each stereocenter.

(e) FK-506 has been shown to exhibit moderate solubility in various organic solvents. Is this immunosuppressant expected to be soluble in ethanol (CH₃CH₂OH)?

(f) Consider the carbon atom labeled “1.” What is the geometry and approximate bond angle of this carbon atom?

(g) Draw the alternative chair conformations of the cyclohexane ring at the lower right of FK-506 and label the more stable conformation. (Chapter 2)

(h) Are there any aromatic components present in FK-506? (Chapter 4)

(i) Patients taking FK-506 have reported several side effects from this medication, including headaches, nausea or diarrhea, and slight shaking. Would you expect the enantiomer of this drug to result in the same side effects?