Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

30. Peptides and Proteins

Merrifield Solid-Phase Peptide Synthesis

Organic Chemistry

30. Peptides and Proteins

Merrifield Solid-Phase Peptide Synthesis

Previous problemNext problem

Struggling with Organic Chemistry?

Join thousands of students who trust us to help them ace their exams!Watch the first video

Multiple Choice

Starting from polystyrene, provide the synthetic pathway in forming the tripeptide Gly-Leu-Ser using the Merrifield peptide synthesis method.

Synthetic pathway for Gly-Leu-Ser tripeptide using Merrifield synthesis.

Merrifield synthesis steps for Gly-Leu-Ser tripeptide formation.

Steps in Merrifield synthesis for tripeptide Gly-Leu-Ser.

Merrifield synthesis pathway for Gly-Leu-Ser tripeptide.

Previous problemNext problem

Verified step by step guidance

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).