Synthesis of Type 1 Lewis b hexasaccharide antigen structures featuring flexible incorporation of L-[U-13C6]-fucose for NMR binding studies
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- 13C-Lewis-OBC-accepted manuscript-D0OB00426J
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Dangosydd eitem ddigidol (DOI)
While 13C-labelled proteins are common tools in NMR studies, lack of access to 13C-labelled carbohydrate structures has restricted their use. L-fucose is involved in a wide range of physiological and pathophysiological processes in mammalian organisms. Here, L-[U-13C6]-Fuc labelled type I Lewis b (Leb) structures have been synthesised for use in NMR binding studies with the Blood-group Antigen Binding Adhesin (BabA), a membrane-bound protein from the bacterium Helicobacter pylori. As part of this work, an efficient synthesis of a benzylated L-[U-13C6]-Fuc thioglycoside donor from L-[U-13C6]-Gal has been developed. The design and synthesis of an orthogonally protected tetrasaccharide precursor enabled controlled introduction of one or two 13C-labelled or non-labelled fucosyl residues prior to global deprotection. NMR analysis showed that it is straightforward to assign the anomeric centres as well as the H-5 positions to the individual fucosyl residues which are relevant for NMR binding studies
Iaith wreiddiol | Saesneg |
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Tudalennau (o-i) | 4452-4458 |
Cyfnodolyn | Organic and Biomolecular Chemistry |
Cyfrol | 18 |
Rhif y cyfnodolyn | 23 |
Dynodwyr Gwrthrych Digidol (DOIs) | |
Statws | Cyhoeddwyd - 21 Meh 2020 |
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