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.

    Full text documents are added when available. The database is updated daily and currently holds about 240,000 items, of which 72,000 in open access.

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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.
Department(s) Food Chemistry Group
FBR Sustainable Chemistry & Technology
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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