A general route to xyloglucan-peptide conjugates for the activation of cellulose surfaces
Artikel i vetenskaplig tidskrift, 2012

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-NH2) 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.

proteins

functionalization

Peptides

rgd

binding

Diethyl squarate

adhesion

crystal-structures

oligosaccharides

plant-cell walls

structural-analysis

Cellulose

Glycoconjugates

Xyloglucan

bacterial cellulose

Författare

A. C. Araujo

Kungliga Tekniska Högskolan (KTH)

A. Nakhai

Kungliga Tekniska Högskolan (KTH)

M. Ruda

AlbaNova University Center

R. Slattegard

AlbaNova University Center

Paul Gatenholm

Chalmers, Kemi- och bioteknik, Polymerteknologi

H. Brumer

Michael Smith Laboratories

Kungliga Tekniska Högskolan (KTH)

Carbohydrate Research

0008-6215 (ISSN)

Vol. 354 116-120

Ämneskategorier

Kemiska processer

DOI

10.1016/j.carres.2012.03.038