Microwave-assisted click polymerization for the synthesis of Aβ(16–22) cyclic oligomers and their self-assembly into polymorphous aggregates

Elgersma, R.C., van Dijk, M., Dechesne, A.C., van Nostrum, C.F., Hennink, W.E., Rijkers, D.T.S. and Liskamp, R.M.J. (2009) Microwave-assisted click polymerization for the synthesis of Aβ(16–22) cyclic oligomers and their self-assembly into polymorphous aggregates. Organic and Biomolecular Chemistry, 7(21), pp. 4517-4525. (doi:10.1039/b912851d)

Full text not currently available from Enlighten.

Abstract

We report on the design, synthesis, and structural analysis of cyclic oligomers with an amyloidogenic peptide sequence as the repeating unit to obtain novel self-assembling bionanomaterials. The peptide was derived from the Alzheimer Aβ(16–22) sequence since its strong tendency to form antiparallel β-sheets ensured the formation of intermolecular hydrogen bridges on which the supramolecular assembly of the individual cyclic oligomers was based. The synthesis of the cyclic oligomers was performed via a microwave-assisted Cu(I)-catalyzed 1,3-dipolar cycloaddition reaction of azido-Lys-Leu-Val-Phe-Phe-Ala-Glu-propargyl amide as the monomer. The formation of cyclic oligomers, up to pentamers (35 amino acid residues), was verified by MALDI-TOF analysis and the individual cyclic monomer and dimer could be isolated by HPLC. Gelation behavior and the self-assembly of the linear monomer and the cyclic monomer and dimer were studied by TEM, FTIR and CD. Significant differences were observed in the morphology of the supramolecular aggregates of these three peptides that could be explained by alterations of the hydrogen bond network.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Liskamp, Professor Robert
Authors: Elgersma, R.C., van Dijk, M., Dechesne, A.C., van Nostrum, C.F., Hennink, W.E., Rijkers, D.T.S., and Liskamp, R.M.J.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Organic and Biomolecular Chemistry
ISSN:1477-0520
ISSN (Online):1477-0539

University Staff: Request a correction | Enlighten Editors: Update this record