Staff Publications

Staff Publications

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    'Staff publications' is the digital repository of Wageningen University & Research

    'Staff publications' contains references to publications authored by Wageningen University staff from 1976 onward.

    Publications authored by the staff of the Research Institutes are available from 1995 onwards.

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Record number 408216
Title Proof of principle for the synthesis of hydroxy-aryl esters of glycosidic polyols and non-reducing oligosaccharides with subsequent enzymatic coupling to a tyrosine-containing tripeptide
Author(s) Haar, R. ter; Wildschut, J.; Sugih, A.K.; Moller, W.B.; Waard, P. de; Boeriu, C.G.; Heeres, H.J.; Schols, H.A.; Gruppen, H.
Source Carbohydrate Research : an international journal 346 (2011)8. - ISSN 0008-6215 - p. 1005 - 1012.
DOI http://dx.doi.org/10.1016/j.carres.2011.03.023
Department(s) Food Chemistry Group
Biophysics
FBR Sustainable Chemistry & Technology
VLAG
Publication type Refereed Article in a scientific journal
Publication year 2011
Keyword(s) cross-linking - sucrose - acid - stability - starch - ph
Abstract To enable enzymatic coupling of saccharides to proteins, several di- and trisaccharides were hydroxy-arylated using anhydrous transesterification with methyl 3-(4-hydroxyphenyl)propionate, catalyzed by potassium carbonate. This transesterification resulted in the attachment of up to 3 hydroxy-aryl units per oligosaccharide molecule, with the monosubstituted product being by far the most abundant. The alkaline reaction conditions, however, resulted in a partial breakdown of reducing sugars. This breakdown could easily be bypassed by a preceding sugar reduction step converting them to polyols. Hydroxy-arylated products were purified by using solid phase extraction, based on the number of hydroxy-aryl moieties attached. Monohydroxy-arylated saccharose was subsequently linked to a tyrosine-containing tripeptide using horseradish peroxidase, as monitored by LC–MSn. This proof of principle for peptide and protein glycation with a range of possible saccharides and glycosidic polyols can lead to products with unique new properties. Highlights ¿ Oligosaccharides and glycosidic polyols are hydroxy-arylated by transesterification. ¿ Hydroxy-arylated oligosaccharides are fractionated using solid phase extraction. ¿ Hydroxy-arylated saccharose is coupled to Gly-Tyr-Gly using horseradish peroxidase. ¿ Proof of principle given for protein glycation via an introduced phenolic linker.
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