Multiple Choice
Provide the peptide chain structure produced from the following sequence of reagents. (Note: Show the ionic forms for the N and C terminus ends).
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30. Peptides and Proteins
Merrifield Solid-Phase Peptide Synthesis
Multiple Choice
Starting from polystyrene, provide the synthetic pathway in forming the tripeptide Gly-Leu-Ser using the Merrifield peptide synthesis method.
A
B
C
D
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Verified step by step guidance1
Start with the Merrifield resin, which is a polystyrene resin functionalized with a chloromethyl group. This will serve as the solid support for peptide synthesis.
Attach the first amino acid, glycine, to the resin. This is done by reacting the resin with a protected form of glycine, such as Boc-Gly-OH, using a coupling agent like DCC (dicyclohexylcarbodiimide) to form an amide bond.
Remove the protecting group from the glycine using an acid, such as trifluoroacetic acid (TFA), to expose the amine group for the next coupling step.
Couple the second amino acid, leucine, to the deprotected glycine on the resin. Use a protected form of leucine, such as Boc-Leu-OH, and DCC as the coupling agent to form the second amide bond.
Repeat the deprotection and coupling steps for the third amino acid, serine, using a protected form like Boc-Ser(OH)-OH. After the final coupling, remove all protecting groups and cleave the tripeptide from the resin using a strong acid like HF (hydrofluoric acid).
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