Modular ligation of thioamide functional peptides onto solid cellulose substrates

Tischer, T., Goldmann, A.S., Linkert, K., Trouillet, V., Börner, H.G., & Barner-Kowollik, C. (2012) Modular ligation of thioamide functional peptides onto solid cellulose substrates. Advanced Functional Materials, 22(18), pp. 3853-3864.

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Hetero Diels-Alder (HDA) cycloaddition - as an effective modular conjugation approach - is employed to graft thioamide endfunctional oligopeptides onto solid cyclopentadienyl (Cp) functional cellulose substrates generating cellulose-peptide hybrid materials. The highly reactive Cp moieties serve as diene functionality in the consecutive HDA reaction on the biosubstrate surface. Oligopeptides (i.e., the model peptide Gly-Gly-Arg-Phe-Pro-Trp-Trp-Gly and the antimicrobial peptide tritrpticin) are functionalized at their N-termini employing strongly electron deficient thiocarbonyl thio compounds resulting in biomacromolecules bearing a thioamide endgroup. The dienophile- functional peptides readily undergo HDA reactions at ambient temperature and under mild conditions in solution with synthetic polymers as well as on solid (bio)substrates. An in-depth investigation is provided of the influence of the temperature, the Lewis acid catalysis and the side group exchange of thioamide functional oligopeptides reacting with Cp terminated poly(methyl methacrylate) (M n = 2100 g·mol -1, PDI = 1.1) in homogenous solution as well as Cp functionalized cellulose in a heterogeneous system. To assess the success of the grafting reaction, the soluble samples were subjected to characterization methods such as size exclusion chromatography (SEC) and SEC-electrospray ionization mass spectrometry (SEC-ESI-MS). The heterogeneous "grafting-to" reactions were monitored using high resolution attenuated total reflection (ATR) Fourier transform infrared microscopy (HR-FTIRM) imaging, X-ray photoelectron spectroscopy (XPS) and elemental analysis. Evaluation via elemental analysis leads to quantitative peptide cellulose surface loading capacities. © 2012 WILEY-VCH Verlag erlag GmbH & Co. KGaA, Weinheim.

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22 citations in Scopus
21 citations in Web of Science®
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ID Code: 99325
Item Type: Journal Article
Refereed: Yes
Keywords: biofunctionalization, cellulose, grafting-to, modular peptide ligation, surface modification, Antimicrobial peptide, Attenuated total reflections, Biomacromolecules, Cellulose substrates, Cellulose surfaces, Characterization methods, Cyclopentadienyls, Dienophiles, Electron-deficient, End groups, Fourier transform infrared microscopies, Functionalized, Grafting reactions, Hetero diels-alder cycloaddition, Heterogeneous systems, High resolution, In-depth investigation, Ionization mass spectrometry, Lewis acid catalysis, Model peptides, Oligopeptides, Synthetic polymers, Thio-compounds, Thioamides, Thiocarbonyl, Cycloaddition, Directive antennas, Esters, Hybrid materials, Loading, Mass spectrometry, Olefins, Peptides, Photoelectrons, Surface reactions, Surface treatment, X ray photoelectron spectroscopy, Grafting (chemical)
DOI: 10.1002/adfm.201200266
ISSN: 1616-301X
Divisions: Current > Schools > School of Chemistry, Physics & Mechanical Engineering
Current > Institutes > Institute for Future Environments
Current > QUT Faculties and Divisions > Science & Engineering Faculty
Deposited On: 22 Sep 2016 04:50
Last Modified: 17 May 2017 00:51

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