Thursday, November 14, 2019

biochemistry - Synthesis of tripeptide using Merrifield peptide synthesis procedure - Inclusion of asparagine


I am supposed to synthesize tripeptide, $\mathrm{Ala-Asn-Phe}$, using Merrifield peptide synthesis procedure. Accordingly, I have done followings:




  1. Attached protected $\mathrm{Phe}$ as the first amino acid.

  2. Got rid of protecting group ($\mathrm{BOC}$)

  3. Added asparagine with 2 protecting groups - $\mathrm{BOC}$ for $\alpha$-$\ce{NH2}$ group and $\mathrm{FMOC}$ for the $\gamma$-$\ce{NH2}$ group.

  4. Got rid of $\mathrm{BOC}$ and added $\mathrm{Ala}$ protected with $\mathrm{BOC}$.

  5. Got rid of $\mathrm{BOC}$ and $\mathrm{FMOC}$, and used $\ce{HF}$ to release the peptide.


Is this going to work? The thing that worries me the most is the $\gamma$-amino group and using $\mathrm{FMOC}$ - is that a good idea?


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