Vancomycin is an especially useful antibiotic for treating infections in cancer patients o...

Vancomycin is an especially useful antibiotic for treating infections in cancer patients on chemotherapy and renal patients on dialysis. Unlike mammalian cells, bacterial cells are surrounded by a fairly rigid cell wall, which is crucial to the bacterium’s survival. Vancomycin kills bacteria by interfering with their cell wall synthesis.

a. How many amide functional groups are present in vancomycin?

b. Which OH groups are bonded to sp3 hybridized carbon atoms and which are bonded to sp2 hybridized carbons?

c. Would you expect vancomycin to be water soluble? Explain.

d. Which proton is the most acidic?

e. Label three different functional groups capable of hydrogen bonding.