A general route to xyloglucan-peptide conjugates for the activation of cellulose surfaces
2012 (English)In: Carbohydrate Research, ISSN 0008-6215, E-ISSN 1873-426X, Vol. 354, 116-120 p.Article in journal (Refereed) Published
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.
Cellulose, Diethyl squarate, Glycoconjugates, Peptides, Xyloglucan
Chemical Sciences Biological Sciences
IdentifiersURN: urn:nbn:se:kth:diva-96039DOI: 10.1016/j.carres.2012.03.038ISI: 000304055100015ScopusID: 2-s2.0-84861183350OAI: oai:DiVA.org:kth-96039DiVA: diva2:529721
FunderSwedish Research Council
QC 201205312012-05-312012-05-302012-06-13Bibliographically approved