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Chemistry: SPPS/Protecting Groups(Boc/Fmoc)/Peptide Question

  1. Jan 23, 2013 #1
    Question with part of answer:
    http://i.imgur.com/5Nki1SM.png

    More answer with questions:
    C-terminus should a carboxylic acid for both as the ester and amide will be acid hydrolyzed.
    The ester linkage should be more susceptible to acid because it is more reactive than the amide. This is because the oxygen is a worse electron donating group than the nitrogen therefore it is stabilized less by resonance. However, do I need to take into account the phenyl groups? They are electron donating and may make the ester stronger.

    Either neither or both are employed with Boc chemistry. Neither because Boc is removed by strong acids and will thus be removed when the bonds are ester/amide bonds are hydrolyzed or both because Boc uses strong acid and the acid hydrolyzation doesn't need a strong acid?

    Either neither or both are employed with Fmoc chemistry for the same reasons. Fmoc will be removed when the amide/ester bonds are base hydrolyzed or it won't be because it needs strong bases like piperidine.

    Thanks for any help
     
  2. jcsd
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