Exploration of an imide capture/N,N-acyl shift sequence for asparagine native peptide bond formation
| Autor: | Reda Mhidia, Nathalie Ollivier, David Crich, Bernard Delpech, Mikhail S. Ermolenko, Oleg Melnyk, Kaname Sasaki, Emmanuelle Boll, Fabien Fécourt |
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| Přispěvatelé: | Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC) |
| Rok vydání: | 2013 |
| Předmět: |
Stereochemistry
education Clinical Biochemistry Molecular Conformation Pharmaceutical Science Peptide Imides 010402 general chemistry 01 natural sciences Biochemistry chemistry.chemical_compound Shift sequence Drug Discovery Peptide bond Asparagine Protecting group Imide Molecular Biology chemistry.chemical_classification [CHIM.ORGA]Chemical Sciences/Organic chemistry 010405 organic chemistry Organic Chemistry 0104 chemical sciences 3. Good health chemistry Intramolecular force Molecular Medicine Peptides Derivative (chemistry) |
| Zdroj: | Bioorganic and Medicinal Chemistry Bioorganic and Medicinal Chemistry, Elsevier, 2013, 21 (12), pp.3479-85. ⟨10.1016/j.bmc.2013.02.053⟩ |
| ISSN: | 0968-0896 1464-3391 |
| Popis: | International audience; Imide capture of a C-terminal peptidylazide with a side-chain thioacid derivative of an N-terminally protected aspartyl peptide leads to the formation of an imide bond bringing the two peptide ends into close proximity. Unmasking of the N(α) protecting group and intramolecular acyl migration results in the formation of a native peptide bond to asparagine. |
| Databáze: | OpenAIRE |
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