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Synthesis and NMR elucidation of novel pentacycloundecane‐based peptides
Author(s) -
Altaib Mohamed S.,
Arvidsson Per I.,
Govender Thavendran,
Maguire Glenn E. M.,
Makatini Maya,
Onajole Oluseye K.,
Kruger Hendrik G.
Publication year - 2010
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.2598
Subject(s) - chemistry , diastereomer , amino acid , stereochemistry , peptide , nuclear magnetic resonance spectroscopy , nmr spectra database , proton nmr , carbon 13 nmr , two dimensional nuclear magnetic resonance spectroscopy , combinatorial chemistry , spectral line , biochemistry , physics , astronomy
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.