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Glycobiology Advance Access originally published online on November 10, 2004
Glycobiology 2005 15(4):437-445; doi:10.1093/glycob/cwi013
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Glycobiology vol. 15 no. 4 © Oxford University Press 2004; all rights reserved.

Synthesis, preliminary characterization, and application of novel surfactants from highly branched xyloglucan oligosaccharides

Lionel Greffe2, Laurence Bessueille3, Vincent Bulone3 and Harry Brumer1,2

2 Department of Biotechnology, Royal Institute of Technology (KTH), AlbaNova University Center, 106 91 Stockholm, Sweden, and 3 Equipe "Organisation et Dynamique des Membranes Biologiques," UMR CNRS 5013, Bâtiment Chevreul, Université Claude Bernard Lyon I, 43 Boulevard du 11 Novembre 1918, 69622 Villeurbanne cedex, France

1 To whom correspondence should be addressed; e-mail: harry{at}biotech.kth.se

Received on September 19, 2004; revised on November 3, 2004; accepted on November 3, 2004

A novel class of nonionic, carbohydrate-based surfactants has been synthesized from the plant polysaccharide xyloglucan. Enzymatic hydrolysis of xyloglucan yielded a series of well-defined, highly branched oligosaccharides that, following reductive amination, were readily conjugated with fatty acids bearing C8 to C18 chains under mild conditions. The critical micelle concentration, determined by tensiometry and dye-inclusion measurements, showed a typical dependence on acyl chain length and was sensitive to the degree of galactosylation of the head group. Several compounds from this new group of surfactants, especially those with C14 and C16 chains, were useful for the extraction of membrane-bound enzyme markers from different plant cell compartments in catalytically active form.

Key words: membrane protein extraction / reductive amination / surfactant / xyloglucan / xyloglucan oligosaccharides


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