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Carbohydr Res ; 346(8): 1005-12, 2011 Jun 01.
Article in English | MEDLINE | ID: mdl-21486666

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-MS(n). 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.


Subject(s)
Glycosides/chemistry , Glycosides/chemical synthesis , Horseradish Peroxidase/metabolism , Hydroxides/chemistry , Oligopeptides/metabolism , Oligosaccharides/metabolism , Polymers/chemistry , Tyrosine/chemistry , Biomimetic Materials/chemistry , Biomimetic Materials/metabolism , Carbohydrate Sequence , Catalase/metabolism , Esterification , Esters , Glycosylation , Oligopeptides/chemistry , Oligosaccharides/chemical synthesis , Oligosaccharides/chemistry , Oxidation-Reduction , Phenols/chemistry , Tyrosine/metabolism
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