Deuterated Disaccharides for the Investigation of Protein-Carbohydrate Interactions-Application of Bioaffinity-and STD-NMR
Titel:
Deuterated Disaccharides for the Investigation of Protein-Carbohydrate Interactions-Application of Bioaffinity-and STD-NMR
Auteur:
Hellebrandt, Wilfried Haselhorst, Thomas Kohli, Thies Bauml, Englbert Peters, Thomas
Verschenen in:
Journal of carbohydrate chemistry
Paginering:
Jaargang 19 (2000) nr. 6 pagina's 769-782
Jaar:
2000
Inhoud:
NMR spectroscopic analysis of carbohydrates often suffers from severe overlap of resonance signals, especially in 1H NMR spectra. Therefore, we synthesized four 2,3,4-trideuterio-α-L-fucose containing disaccharides, α-L-Fuc-(1→6)-β-D-GlcNAc-OMe 1, α-L-Fuc-(1→4)-β-D-GlcNAc-OMe 2, α-L-Fuc-(1→3)-β-D-GlcNAc-OMe 3, and α-L-Fuc-(1→2)-β-D-Gal-OMe 4. Compounds 1 to 4 are well suited to be subjected to NMR conformational analysis because their 1H NMR spectra show almost no overlap of signals. The deuterated disaccharides 1 to 4 will therefore be used as NMR probes for the exploration of fucose-binding proteins. With a mixture of the corresponding non-deuterated disaccharides it is demonstrated that recently developed parallel NMR screening protocols, Bio-Affinity NMR and STD-NMR, deliver fast and robust tools to assay the compounds synthesized for protein-binding affinity.