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A general route to xyloglucan-peptide conjugates for the activation of cellulose surfaces
KTH, School of Biotechnology (BIO), Glycoscience.
KTH, School of Biotechnology (BIO), Glycoscience.
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2012 (English)In: Carbohydrate Research, ISSN 0008-6215, E-ISSN 1873-426X, Vol. 354, 116-120 p.Article in journal (Refereed) Published
Abstract [en]

Cellulose is an attractive supporting matrix for diverse biotechnological applications, including chromatography, diagnostics, and tissue replacement/scaffolding, due to its renewable resource status, low cost, and low non-specific interaction with biomolecules. In an effort to expand the biofunctionality of cellulose materials, we present here a versatile method for the synthesis of xyloglucan-peptide conjugates that harness the strong xyloglucan-cellulose binding interaction for gentle surface modification. Xylogluco-oligosaccharide aminoalditols (XGO-NH 2) were coupled to both linear and cyclic peptides, which contained the endothelial cell epitope Arg-Gly-Asp, in a facile two-step approach employing diethyl squarate cross-linking. Subsequent xyloglucan endo-transglycosylase-mediated coupling of the resulting XGO-GRGDS (Gly-Arg-Gly-Asp-Ser) and XGO-c[RGDfK]-PEG-PEG (cyclo[Arg-Gly-Asp-(d-Phe)-Lys]-PEG-PEG; where PEG is 8-amino-3,6-dioxaoctanoic acid) conjugates into high molecular mass xyloglucan yielded xyloglucan-RGD peptide conjugates suitable for cellulose surface activation. Notably, use of XGO-squaramate as a readily accessible, versatile intermediate overcomes previous limitations of solid-phase synthetic approaches to XGO-peptide conjugates, and furthermore allows the method to be generalized to a wide variety of polypeptides and proteins, as well as diverse primary amino compounds.

Place, publisher, year, edition, pages
2012. Vol. 354, 116-120 p.
Keyword [en]
Cellulose, Diethyl squarate, Glycoconjugates, Peptides, Xyloglucan
National Category
Chemical Sciences Biological Sciences
Identifiers
URN: urn:nbn:se:kth:diva-96039DOI: 10.1016/j.carres.2012.03.038ISI: 000304055100015Scopus ID: 2-s2.0-84861183350OAI: oai:DiVA.org:kth-96039DiVA: diva2:529721
Funder
Swedish Research Council
Note
QC 20120531Available from: 2012-05-31 Created: 2012-05-30 Last updated: 2017-12-07Bibliographically approved

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