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).

View at publisher

Abstract

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.

Impact and interest:

19 citations in Scopus
Search Google Scholar™
20 citations in Web of Science®

Citation counts are sourced monthly from Scopus and Web of Science® citation databases.

These databases contain citations from different subsets of available publications and different time periods and thus the citation count from each is usually different. Some works are not in either database and no count is displayed. Scopus includes citations from articles published in 1996 onwards, and Web of Science® generally from 1980 onwards.

Citations counts from the Google Scholar™ indexing service can be viewed at the linked Google Scholar™ search.

ID Code: 99325
Item Type: Journal Article
Refereed: Yes
Additional Information: Cited By :18
Export Date: 5 September 2016
CODEN: AFMDC
Correspondence Address: Börner, H.G.; Laboratory for Organic Synthesis of Functional Systems, Department of Chemistry, Humboldt-Universität zu Berlin, Brook-Taylor-Str. 2, 12489 Berlin, Germany; email: h.boerner@hu-berlin.de
References: Heinze, T., (2009) Macromol. Symp., 280, pp. 15-27; Heinze, T., Liebert, T., (2001) Prog. Polym. Sci., 26, pp. 1689-1762; Roy, D., Semsarilar, M., Guthrie, J.T., Perrier, S., (2009) Chem. Soc. Rev., 38, pp. 2046-2064; Liu, C.-F., Zhang, A.-P., Li, W.-Y., Yue, F.-X., Sun, R.-C., (2009) J. Agric. Food Chem., 57, pp. 1814-1820; Furuhata, K., (1995) Carbohydr. Polym., 26, pp. 25-29; Hussain, M.A., Liebert, T., Heinze, T., (2004) Macromol. Rapid Commun., 25, pp. 916-920; Zhao, G.-L., Hafrén, J., Deiana, L., Córdova, A., (2010) Macromol. Rapid Commun., 31, pp. 740-744; Krouit, M., Bras, J., Belgacem, M., (2008) Eur. Polym. J., 44, pp. 4074-4081; Malmström, E., Carlmark, A., unpublishedMånsson, P., Westfelt, L., (1981) J. Polym. Sci.: Part A: Polym. Chem., 19, pp. 1509-1515; Biermann, C.J., Chung, J.B., Narayan, R., (1987) Macromolecules, 20, pp. 954-957; Tsubokawa, N., Iida, T., Takayama, T., (2000) J. Appl. Polym. Sci., 75, pp. 515-522; Hentschel, J., Bleek, K., Ernst, O., Lutz, J.-F., Börner, H.G., (2008) Macromolecules, 41, pp. 1073-1075; Barsbay, M., Güven, O., Davis, T.P., Barner-Kowollik, C., Barner, L., (2009) Polymer, 50, pp. 973-982; Barsbay, M., Güven, O., Stenzel, M.H., Davis, T.P., Barner-Kowollik, C., Barner, L., (2007) Macromolecules, 40, pp. 7140-7147; Carlmark, A., Malmström, E., (2002) J. Am. Chem. Soc., 124, pp. 900-901; Carlmark, A., Malmström, E.E., (2003) Biomacromolecules, 4, pp. 1740-1745; Roy, D., Guthrie, J.T., Perrier, S., (2005) Macromolecules, 38, pp. 10363-10372; Nebhani, L., Schmiedl, D., Barner, L., Barner-Kowollik, C., (2010) Adv. Funct. Mater., 20, pp. 2010-2020; Kaupp, M., Vogt, A.P., Natterodt, J.C., Trouillet, V., Gruendling, T., Hofe, T., Barner, L., Barner-Kowollik, C., b) unpublishedGoldmann, A.S., Tischer, T., Barner, L., Bruns, M., Barner-Kowollik, C., (2011) Biomacromolecules, 12, pp. 1137-1145; Ten Cate, M.G.J., Rettig, H., Bernhardt, K., Börner, H.G., (2005) Macromolecules, 38, pp. 10643-10649; Becker, M.L., Liu, J., Wooley, K.L., (2004) Biomacromolecules, 6, pp. 220-228; Klemm, D., Heublein, B., Fink, H.P., Bohn, A., (2005) Angew. Chem., Int. Ed., 44, pp. 3358-3393; Siró, I., Plackett, D., (2010) Cellulose, 17, pp. 459-494; Stenstad, P., Andresen, M., Tanem, B.S., Stenius, P., (2007) Cellulose, 15, pp. 35-45; Klemm, D., Kramer, F., Moritz, S., Lindström, T., Ankerfors, M., Gray, D., Dorris, A., (2011) Angew. Chem., Int. Ed., pp. 2-31; Moad, G., Solomon, D.H., (2006) The Chemistry of Radical Polymerization, , 2nd edition, Elsevier Ltd, Oxford; Inglis, A.J., Sinnwell, S., Davis, T.P., Barner-Kowollik, C., Stenzel, M.H., (2008) Macromolecules, 41, pp. 4120-4126; Sinnwell, S., Inglis, A.J., Stenzel, M.H., Barner-Kowollik, C., (2008) Macromol. Rapid Commun., 29, pp. 1090-1096; Nebhani, L., Gerstel, P., Atanasova, P., Bruns, M., Barner-Kowollik, C., (2009) J. Polym. Sci.: Part A: Polym. Chem., 47, pp. 7090-7095; Nebhani, L., Sinnwell, S., Inglis, A.J., Stenzel, M.H., Barner-Kowollik, C., Barner, L., (2008) Macromol. Rapid Commun., 29, pp. 1431-1437; Inglis, A.J., Stenzel, M.H., Barner-Kowollik, C., (2009) Macromol. Rapid Commun., 30, pp. 1792-1798; Nebhani, L., Sinnwell, S., Lin, C.Y., Coote, M.L., Stenzel, M.H., Barner-Kowollik, C., (2009) J. Polym. Sci.: Part A: Polym. Chem., 47, pp. 6053-6071; Inglis, A., Sinnwell, S., Stenzel, M., Barner-Kowollik, C., (2009) Angew. Chem., Int. Ed., 48, pp. 2411-2414; Inglis, A.J., Paulöhrl, T., Barner-Kowollik, C., (2010) Macromolecules, 43, pp. 33-36; Danishefsky, S., Larson, E., Askin, D., Kato, N., (1985) J. Am. Chem. Soc., 107, pp. 1246-1255; Hansson, S., Tischer, T., Goldmann, A.S., Carlmark, A., Barner-Kowollik, C., Malmström, E., (2012) Polym. Chem., 1500, pp. 10-12; Jagst, E., (2010) Surface Functional Group Characterization Using Chemical Derivatization X-ray Photoelectron Spectroscopy (CD-XPS), , BAM, Berlin, Germany; Amaral, I.F., Granja, P.L., Barbosa, M.A., (2005) J. Biomater. Sci., Polym. Ed., 16, pp. 1575-1593; Hintz, H., Egelhaaf, H.-J., Peisert, H., Chassé, T., (2010) Polym. Degrad. Stab., 95, p. 818; Wang, L.-P., Wang, Y.-P., Yuan, K., Lei, Z.-Q., (2008) Polym. Adv. Technol., 19, pp. 285-290; Abrunhosa, I., Gulea, M., Masson, S., (2004) Synthesis, pp. 928-934; Stickler, M., Panke, D., Wunderlich, W., (1987) Makromol. Chem., 188, pp. 2651-2664; Koo, S.P.S., Junkers, T., Barner-Kowollik, C., (2008) Macromolecules, 42, pp. 62-69; Parry, K.L., Shard, A.G., Short, R.D., White, R.G., Whittle, J.D., Wright, A., (2006) Surf. Interface Anal., 38, pp. 1497-1504; Scofield, J.H., (1976) J. Electron Spectrosc. Relat. Phenom., 8, pp. 129-137
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: 1616301X
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: 30 Sep 2016 05:05

Export: EndNote | Dublin Core | BibTeX

Repository Staff Only: item control page