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    This structure of the drug seems to have an amide group based on the general amide expression. But the confusion is about it being a protein Proline ( which has a heterocyclic ring ). Does it count as a pyrrolidine ring only or can it also be an amide?



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    It has both an amide group and a pyrrolidine ring
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    (Original post by oZu)
    This structure of the drug seems to have an amide group based on the general amide expression. But the confusion is about it being a protein Proline ( which has a heterocyclic ring ). Does it count as a pyrrolidine ring only or can it also be an amide?
    It most certainly is not a protein!

    It's not either an amide or a pyrrolidine ring, it contains both moieties, as EvS says. You don't need to decide between the two
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    Thank you, appreciate the help. I have one more tiny query: the same structure..
    It has 2 H bond donors (which are obvious) and 3 acceptors. Now I am wondering:
    Nitrogen cannot be an acceptor because its electrons are in the cyclic structure (right?), so it leaves the sulphur atom, and both oxygens with double bonds..
    Am I going the right way?

    Cheers

    (Original post by Plato's Trousers)
    It most certainly is not a protein!

    It's not either an amide or a pyrrolidine ring, it contains both moieties, as EvS says. You don't need to decide between the two
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    (Original post by oZu)
    Thank you, appreciate the help. I have one more tiny query: the same structure..
    It has 2 H bond donors (which are obvious) and 3 acceptors. Now I am wondering:
    Nitrogen cannot be an acceptor because its electrons are in the cyclic structure (right?), so it leaves the sulphur atom, and both oxygens with double bonds..
    Am I going the right way?

    Cheers

    acceptors have to have a lone pair and be electronegative, so it's your three oxygen atoms.
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    Makes sense - what about the sulphur? I know it is capable of disulfide bonds so surely it should be a H acceptor? has 2 pairs of lone pairs as well :]

    (Original post by Plato's Trousers)
    acceptors have to have a lone pair and be electronegative, so it's your three oxygen atoms.
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    Sulphur doesn't really form accept hydrogen bonds in a meaning sense - it's not electronegative enough and being second row it's electrons are more diffuse and spread out.

    You can get a sense of relative h-bond strength from water and H2S. H2S boils at -60C, so there's clearly an awful lot less hydrogen bonding going on compared to water.
 
 
 
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