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Synthesis of Hybrid Peptidomimetics and Neoglycoconjugates Employing Click Protocol: Dual Utility of Poc-Group for Inserting Carbamate-Triazole Units into Peptide Backbone

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Abstract

Synthesis of new types of peptidomimetics and glycosylated amino acids possessing 1,2,3-triazole and carbamate moieties is described. Poc-protected amino acid esters/1-amino sugars were subjected to Cu(I) catalyzed [2+3]cycloaddition with desired azides under click protocol to obtain novel peptide and carbohydrate mimetics. The reaction is rapid, efficient and all the products are isolated in good yield and excellent purity.

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Acknowledgments

We thank the Department of Science and Technology (DST), Govt. of India (Grant no. SR/S1/OC/26-2008) and Council of Scientific and Industrial Research (CSIR), New Delhi (Grant No. 01(2323)/09/EMR-II) for the financial assistance. One of the authors RSL thanks University Grants Commission, New Delhi for the award of Dr. D. S. Kothari Postdoctoral Fellowship. Departments of Organic Chemistry and Inorganic & Physical Chemistry, Indian Institute of Science, Bangalore, India are thanked for spectral data.

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  1. Peptide Research Laboratory, Department of Studies in Chemistry, Central College Campus, Bangalore University, Dr. B. R. Ambedkar Veedhi, Bangalore, 560 001, India

    Hosahalli P. Hemantha, Ravi S. Lamani & Vommina V. Sureshbabu

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  1. Hosahalli P. Hemantha
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  2. Ravi S. Lamani
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  3. Vommina V. Sureshbabu
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Correspondence to Vommina V. Sureshbabu.

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Hemantha, H.P., Lamani, R.S. & Sureshbabu, V.V. Synthesis of Hybrid Peptidomimetics and Neoglycoconjugates Employing Click Protocol: Dual Utility of Poc-Group for Inserting Carbamate-Triazole Units into Peptide Backbone. Int J Pept Res Ther 16, 267–275 (2010). https://doi.org/10.1007/s10989-010-9228-6

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