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CuI-Promoted One-Pot Synthesis of N-Boc Protected β-Ketotriazole Amino Acids: Application in the Synthesis of New Class of Dipeptidomimetics

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Abstract:

One-pot click chemistry of Nα-Boc-bromomethylketones, NaN3 and propiolic acid affords N-Boc protected 1,4- disubstituted 1,2,3-β-ketotriazole acids in good to excellent yield. The use of CuI as catalyst and DMSO as solvent leads the click reaction to efficient, practical and column-free preparation of the title compounds. The utility of the resulting unnatural amino acids as building blocks to prepare triazole possessing peptidomimetics is also delineated.





Keywords: CuI; N-Boc-protected 1,4-disubstituted 1,2,3β-ketotriazole; N-Boc-protected 1,4-disubstituted 1,2,3β-ketotriazole amino acids; Nα-Boc-bromomethylketones; amino acids; dimethylacetylenedicarboxylate; halides; nanotubes; one-pot click chemistry; peptidomimetics; triazole

Document Type: Research Article

DOI: https://doi.org/10.2174/092986612799363172

Publication date: 2012-03-01

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  • Protein & Peptide Letters publishes short papers in all important aspects of protein and peptide research, including structural studies, recombinant expression, function, synthesis, enzymology, immunology, molecular modeling, drug design etc. Manuscripts must have a significant element of novelty, timeliness and urgency that merit rapid publication. Reports of crystallisation, and preliminary structure determinations of biologically important proteins are acceptable. Purely theoretical papers are also acceptable provided they provide new insight into the principles of protein/peptide structure and function.
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