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Synthesis and NMR elucidation of novel pentacycloundecane-based peptides

✍ Scribed by Mohamed S. Altaib; Per I. Arvidsson; Thavendran Govender; Glenn E. M. Maguire; Maya Makatini; Oluseye K. Onajole; Hendrik G. Kruger

Book ID
102531533
Publisher
John Wiley and Sons
Year
2010
Tongue
English
Weight
160 KB
Volume
48
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

The synthesis and NMR elucidation of two novel pentacycloundecane (PCU)‐based peptides are reported. The PCU cage amino acids were synthesised as racemates and the incorporation of the cage amino acid with (S)‐natural amino acids produced diastereomeric peptides. The diastereomeric ‘cage’ peptides were separated using preparative HPLC and the NMR elucidation of these PCU containing peptides are reported for the first time. The ^1^H and ^13^C NMR spectra showed series of overlapping signals of the cage skeleton and that of the peptide, making it extremely difficult to resolve the structure using one‐dimensional NMR techniques only. The use of two‐dimensional NMR techniques proved to be a highly effective tool in overcoming this problem. Copyright © 2010 John Wiley & Sons, Ltd.

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