South African Journal of Chemistry

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Synthesis and NMR Elucidation of Novel Pentacycloundecane-Derived Peptides

R Karpoormath, OK Onajole, T Naicker, T Govender, GEM Maguire, HG Kruger


Herein we report the synthesis and NMR elucidation of five novel pentacycloundecane (PCU)-derived short peptides as potential HIV protease inhibitors. 1H and 13C spectral analysis show major overlapping of methine resonance of the PCU ‘cage’ thereby making it extremely difficult to assign the NMR signals. Attachment of short peptides to the cage at position C-8/C-11 results in conformational differences of the peptide side chains due to diastereomeric interactions between the cage skeleton and the chiral side chains. The use of two-dimensional NMR techniques proved to be highly effective in the elucidation of such systems.

Keywords: 1H NMR, 13C NMR, 2D NMR, PCU diol diaminoacid, HIV protease inhibitors


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