6533b85dfe1ef96bd12bdd6d
RESEARCH PRODUCT
Peptide synthesis with 5-amino-1-methyl-1H-[1,2,4]triazole-3-carboxylic acid
Irena Wawrzycka-gorczycaBarbara RzeszotarskaEdyta KołodziejczykElzbieta Masiukiewiczsubject
chemistry.chemical_classification4]triazole-3-carboxylic acidStereochemistryNMR spectraLexitropsinCarboxylic acidAcylationOrganic Chemistry2124-TriazolePeptideGeneral MedicineCombinatorial chemistry5-amino-1-methyl-1H-[1Acylationchemistry.chemical_compoundHydrolysisPeptide synthesischemistryFTIR spectraHetareneamino acidPeptide synthesisBenzotriazolideDerivative (chemistry)description
Abstract In the search for the peptide synthesis of new potential lexitropsins, starting with methyl 5‐amino‐1‐methyl‐1H‐[1,2,4]triazole‐3‐carboxylate 1a, we synthesized the chloroacetyl derivative of 2a, which was hydrolyzed to acid 2b and ammonolyzed to the peptide 2c. A more effective route was the use of (t‐butoxycarbonyl)glycyl‐benzotriazolide 3 to the acylation 1a, which leads the N/C protected peptide 4. This peptide was selectively N‐deprotected to be the useful segment 5 for further peptide syntheses to the N‐terminus. It was also C‐deprotected, that is hydrolyzed to give peptide 2c for further C‐extension. To the best of our knowledge, this is the first peptide that is a derivative of amino‐1‐methyl‐1H‐[1,2,4]triazole‐carboxylic acid.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2007-06-01 | Synthetic Communications |