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Peptidomimetics Through Click Chemistry: Synthesis of Novel β-Keto Triazole Acids from N-Protected Amino Acids

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Abstract

An efficient procedure for the preparation of azidomethylketones from N-urethane protected amino acids and their application in Cu(I) catalyzed azide-alkyne cycloaddition reaction are described. The synthesis has been carried out under mild conditions with all the commonly used urethane protected (Fmoc, Boc and Z) amino acids and the desired azides/triazoles were obtained in good yields. Incorporation of these triazole amino acids into small peptides generating dipeptidomimetics containing β-keto triazole units has also been demonstrated.

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Acknowledgement

The authors thank the Department of Science and Technology, Government of India for the financial assistance (Grant No. SR/S1/OC-26/2008).

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Authors and Affiliations

  1. Peptide Research Laboratory, Department of Studies in Chemistry, Bangalore University, Central College Campus, Dr. B. R. Ambedkar Veedhi, Bangalore, 560001, India

    N. Narendra, T. M. Vishwanatha & Vommina V. Sureshbabu

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  1. N. Narendra
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  2. T. M. Vishwanatha
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  3. Vommina V. Sureshbabu
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Correspondence to Vommina V. Sureshbabu.

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Narendra, N., Vishwanatha, T.M. & Sureshbabu, V.V. Peptidomimetics Through Click Chemistry: Synthesis of Novel β-Keto Triazole Acids from N-Protected Amino Acids. Int J Pept Res Ther 16, 283–290 (2010). https://doi.org/10.1007/s10989-010-9214-z

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