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Synthesis and NMR elucidation of novel pentacycloundecane-based peptides
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
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2010 (English)In: Magnetic Resonance in Chemistry, ISSN 0749-1581, E-ISSN 1097-458X, Vol. 48, no 6, 435-442 p.Article in journal (Refereed) Published
Abstract [en]

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 H-1 and C-13 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.

Place, publisher, year, edition, pages
2010. Vol. 48, no 6, 435-442 p.
Keyword [en]
PCU peptides, AVPI, 2D NMR, beta-turns, structure elucidation
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:uu:diva-136208DOI: 10.1002/mrc.2598ISI: 000278041200003PubMedID: 20474021OAI: oai:DiVA.org:uu-136208DiVA: diva2:376463
Available from: 2010-12-10 Created: 2010-12-10 Last updated: 2017-12-11Bibliographically approved

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