Vancomycin is a useful antibiotic for treating infections in...

Vancomycin is a 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 $sp^3$ hybridized carbon atoms and which are bonded to $sp^2$ 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.

Transcript

00:01 Remember that an amide functional group has the following general structure.

00:07 It has a carbonyl region.

00:11 I'll redraw that.

00:12 It has a carbonyl region.

00:15 And then it has the nitrogen region here with two other substituents labeled r.

00:26 So with this in mind, as the general structure of the amide, how many amide functional groups are in this molecule, which is vasolmycin, the antibiotic.

00:38 Well, i'll circle them in green.

00:43 Most obviously, we have this one right here.

00:46 Again, we have this nitrogen, and we have h's in place of these two substituents.

00:54 And i don't believe there are any others in this molecule.

00:59 So we just have one.

01:01 So we have one amide there.

01:07 Now we're asked about the alcohol hydroxide, excuse me, hydroxyl groups attached to sp3 hybridized carbons.

01:18 So remember that an sp3 hybridized carbon consists of a tetrahedral structure.

01:27 So, for example, this methane molecule here is sp3 hybridized, and it's in a tetrahedral shape.

01:41 So really, we just need to look for saturated carbons with tetrahedral geometries to know where the sp3 hybridized carbons are.

01:52 And on the other hand, to find the sp2 carbons, we know sp2 carbons have double bonds, and they are, for example, this eth here is an sp2 hybridized.

02:11 So right here, we have a sp2 hybridized carbon because we have a double bond here between the c and the o.

02:26 So this is one sp2 hybridized oxygen.

02:32 This is, or oxygen attached to an sp2 hybridized carbon.

02:37 Same thing here, because we have an sp2 hybridized.

02:40 Oops, there.

02:43 Again, here, here, here we have an sp3 hybridized.

02:50 I'll do that in blue because we have a saturated tetrahedral center there.

02:57 We have again sp3 sp3 sp3 sp3 there sp3 here and i believe that is all so we have whoa what happened there i do not know we're just going to fix that up there so yeah so vanso mycin is going to be water soluble and to determine something is water soluble, we need to think about the polarity of the molecule because polar molecules dissolve in polar solvents and water is a polar solvent, light dissolves light.

03:47 So we know that this is going to be a polar molecule because the electron density in this thing is surely not evenly distributed.

03:55 We have many oxygens, many nutrients, many aromatic rings.

04:01 We have sugars here...

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