Comparison of various coupling reagents in solid-phase aza-peptide synthesis
| Autor: | Jaak Järv, Anton Mastitski, Meeli Arujõe, Anu Ploom |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
chemistry.chemical_classification
Semicarbazide 010405 organic chemistry Stereochemistry Organic Chemistry Kinetics Peptide 010402 general chemistry 01 natural sciences Biochemistry 0104 chemical sciences Amino acid Acylation chemistry.chemical_compound chemistry Reagent Drug Discovery Peptide synthesis Moiety |
| Zdroj: | Tetrahedron Letters. 58:3421-3425 |
| ISSN: | 0040-4039 |
| DOI: | 10.1016/j.tetlet.2017.07.063 |
| Popis: | Aza-peptides are promising drug leads, however extensive study of their properties is hampered by low yielding aza-peptide bond formation during conventional Fmoc SPPS. The kinetics of aza-peptide bond formation in the model peptide H-Ala-AzAla-Phe-NH 2 was compared with various conventional amino acid activators. The reaction rates and yields were dependent on the activator structure. The reaction time of aza-peptide formation using oxyma-based agents was approximately 30 times longer than in typical peptide synthesis. Therefore, new activators are required to increase the reactivity of the activated amino acid to achieve effective acylation of the semicarbazide moiety during aza-peptide bond formation. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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