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

Author(s): T. M. Vishwanatha, N. Narendra, Vommina V. Sureshbabu

Journal Name: Protein & Peptide Letters

Volume 19 , Issue 3 , 2012

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

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Article Details

Year: 2012
Page: [308 - 314]
Pages: 7
DOI: 10.2174/092986612799363172
Price: $65

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