title: A general route to xyloglucan-peptide conjugates for the activation of cellulose surfaces.
abstract: 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.
authors.affiliation: Division of Glycoscience, School of Biotechnology, Royal Institute of Technology (KTH), AlbaNova University Center, 106 91 Stockholm, Sweden.
authors.forename: Ana Catarina
authors.initials: AC
authors.lastname: Araújo
authors.forename: Azadeh
authors.initials: A
authors.lastname: Nakhai
authors.forename: Marcus
authors.initials: M
authors.lastname: Ruda
authors.forename: Rikard
authors.initials: R
authors.lastname: Slättegård
authors.forename: Paul
authors.initials: P
authors.lastname: Gatenholm
authors.forename: Harry
authors.initials: H
authors.lastname: Brumer
mesh_terms: D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002482:Cellulose / Q000737:chemistry*; D005936:Glucans / Q000737:chemistry*; D008969:Molecular Sequence Data; D010455:Peptides / Q000737:chemistry*; D013499:Surface Properties; D014990:Xylans / Q000737:chemistry*
chemical_list: D005936:Glucans; D010455:Peptides; D014990:Xylans; C029353:xyloglucan; D002482:Cellulose