Dicyclopropylmethyl Peptide Backbone Protectant†
| Autor: | Eberhard Krause, Adel Ali Abdel-Maksoud, Holger Wenschuh, Ayman El-Faham, Michael Beyermann, Michael Bienert, Peter Henklein, Louis A. Carpino, Dumitru Ionescu, Khaled Nasr |
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| Rok vydání: | 2009 |
| Předmět: |
Cyclopropanes
chemistry.chemical_classification Alanine Molecular Structure integumentary system Stereochemistry Sodium cyanoborohydride Organic Chemistry Peptide Dipeptides Biochemistry Catalysis Article Amino acid Structure-Activity Relationship chemistry.chemical_compound Residue (chemistry) chemistry Peptide synthesis Peptide bond Amino Acid Sequence Amino Acids Physical and Theoretical Chemistry Oligopeptides Peptide sequence |
| Zdroj: | Organic letters, 11(16): 3718–3721 |
| ISSN: | 1523-7052 1523-7060 |
| Popis: | The N-dicyclopropylmethyl (Dcpm) residue, introduced into amino acids via reaction of dicyclopropylmethanimine hydrochloride with an amino acid ester followed by sodium cyanoborohydride or triacetoxyborohydride reduction, can be used as an amide bond protectant for peptide synthesis. Examples which demonstrate the amelioration of aggregation effects include syntheses of the alanine decapeptide and the prion peptide (106-126). Avoidance of cyclization to the aminosuccinimide followed substitution of Fmoc-(Dcpm)Gly-OH for Fmoc-Gly-OH in the assembly of sequences containing the sensitive Asp-Gly unit. |
| Databáze: | OpenAIRE |
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