Solid Phase Synthesis
Source: Vy M. Dong and Diane Le, Department of Chemistry, University of California, Irvine, CA
Merrifield's solid-phase synthesis is a Nobel Prize winning invention where a reactant molecule is bound on a solid support and undergoes successive chemical reactions to form a desired compound. When the molecules are bound to a solid support, excess reagents and byproducts can be removed by washing away the impurities, while the target compound remains bound to the resin. Specifically, we will showcase an example of solid-phase peptide synthesis (SPPS) to demonstrate this concept.
1. Loading the Resin
- To a 100mL peptide synthesis vessel, add 2-chlorotrityl chloride (CTC) resin (1.1 mmol/g, 0.360 g, 0.400 mmol). Add 20 mL DMF and allow them to swell for 30 min under N2.
- Drain the beads under vacuum and add 10 mL DMF.
- Add 500 mg Fmoc-Ala-OH (1.60 mmol) and 2.5 mL i-Pr2EtN, and mix under N2 for 15 min.
- Drain the solvent under vacuum and repeat the loading with Fmoc-Ala-OH for 15 min.
- Drain the solvent under
Representative results for solid phase peptide synthesisfor Procedure 3.
| Procedure Step | Color of solution |
| 3.1 | Control - Clear, light yellow Reaction – Clear, light yellow |
| 3.2 | Control - Clear, light yellow Reaction – Dark blue |
| 3.3 | Dark blue solution, beads blue – c Application and Summary In this experiment, we have demonstrated an example of solid-phase synthesis via SPPS through the synthesis of a dipeptide. Solid-phase synthesis is widely used in combinatorial chemistry to build up libraries of compounds for rapid screening. It has been commonly used to synthesize peptides, oligosaccharides, and nucleic acids. Moreover, this concept has been implemented in chemical synthesis. Because it is heterogeneous, these solid-supported reagents can often be recycled and reused in subs Tags Solid Phase SynthesisMethodSynthesizedBoundInsoluble MaterialBiological OligomersPolymersPeptidesNucleic AcidsOligosaccharidesChainsMonomersCorrect OrderMulti step SynthesesPurificationIsolationStable ProductsIntermediate ProductsOverall YieldSolid SupportSolution phase ReagentsSolventsByproductsWashed AwayPurifyIsolateStepsSolid phase Peptide SynthesisApplications In Chemistry Skip to... ABOUT JoVE Copyright © 2024 MyJoVE Corporation. All rights reserved |
