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.

Cellulose

binding

Glycoconjugates

oligosaccharides

Peptides

bacterial cellulose

Xyloglucan

rgd

functionalization

Diethyl squarate

structural-analysis

adhesion

proteins

plant-cell walls

crystal-structures

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

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Senast uppdaterat

2019-04-10