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Synthesis and NMR elucidation of pentacycloundecane-derived hydroxy acid peptides as potential anti-HIV-1 agents

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Abstract

The synthesis and NMR elucidation of eight novel peptides incorporating the pentacycloundecane (PCU)-derived hydroxy acid are reported. The PCU cage amino acids were synthesized as racemates and the incorporation of the PCU-derived hydroxy acid with natural (S)-amino acids produced inseparable diastereomeric peptides. A series of overlapping signals from the cage and that of the peptide side chain was observed in the 1H- and 13C-NMR spectra, complicating the elucidation thereof. Two-dimensional NMR techniques proved to be a very useful tool in overcoming these difficulties. These compounds are potential HIV protease inhibitors.

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Acknowledgments

This research was supported by NRF (SA) TG (GUN: 66319), HGK (GUN: 69728), HGK and PIA (SA-Sweden bilateral grant), Aspen Pharmacare and University of KwaZulu-Natal for financial support. We thank Mr. Dilip Jagjivan (UKZN, South Africa) for his assistance with the NMR experiments.

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Authors and Affiliations

  1. Catalysis and Peptide Research Unit, School of Health Sciences, University of KwaZulu-Natal, Durban, 4001, South Africa

    Fernando Albericio, Thavendran Govender, Glenn E. M. Maguire & Hendrik G. Kruger

  2. School of Pharmaceutical Sciences, University of KwaZulu-Natal, Durban, 4001, South Africa

    Rajshekhar Karpoormath

  3. Institute for Research in Biomedicine, Barcelona Science Park, Baldiri Reixac 10, 08028, Barcelona, Spain

    Fernando Albericio

  4. CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine, Barcelona Science Park, Baldiri Reixac 10, 08028, Barcelona, Spain

    Fernando Albericio

  5. Department of Organic Chemistry, University of Barcelona, Martí i Franqués 1-11, 08028, Barcelona, Spain

    Fernando Albericio

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  1. Rajshekhar Karpoormath
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  2. Fernando Albericio
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  3. Thavendran Govender
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  4. Glenn E. M. Maguire
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  5. Hendrik G. Kruger
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Corresponding author

Correspondence to Hendrik G. Kruger.

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Karpoormath, R., Albericio, F., Govender, T. et al. Synthesis and NMR elucidation of pentacycloundecane-derived hydroxy acid peptides as potential anti-HIV-1 agents. Struct Chem 24, 1461–1471 (2013). https://doi.org/10.1007/s11224-012-0164-2

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  • DOI: https://doi.org/10.1007/s11224-012-0164-2

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