The synthesis of the trisaccharide α-L-Fucp-(1→2)-β-D-Galp-(1→3)- β-D-Galp2AcOPr (3), mimicking the globo-H terminal trisaccharide unit (2), is described. The conformational properties of 3 were investigated with the aid of molecular mechanics energy minimizations, molecular dynamics simulations, and 1H-NMR spectroscopic analysis and resulted in strict analogy with those of 2. Nevertheless, analysis of MBr1 binding to these compounds indicate that substitution of the acetamido group at C-2 with the ester group lowers the affinity, thus suggesting that the amide hydrogen atom of 2 is involved in intermolecular interactions with the MBr1 antibody.
Synthesis, modeling and binding affinity of an ester analogue of the terminal trisaccharide of the tumor-associated antigen globo-H-1 / S. Canevari, D. Colombo, F. Compostella, L. Panza, F. Ronchetti, G. Russo, L. Toma. - In: TETRAHEDRON. - ISSN 0040-4020. - 55:5(1999), pp. 1469-1478.
Synthesis, modeling and binding affinity of an ester analogue of the terminal trisaccharide of the tumor-associated antigen globo-H-1
D. ColomboSecondo
;F. Compostella;F. Ronchetti;G. RussoPenultimo
;
1999
Abstract
The synthesis of the trisaccharide α-L-Fucp-(1→2)-β-D-Galp-(1→3)- β-D-Galp2AcOPr (3), mimicking the globo-H terminal trisaccharide unit (2), is described. The conformational properties of 3 were investigated with the aid of molecular mechanics energy minimizations, molecular dynamics simulations, and 1H-NMR spectroscopic analysis and resulted in strict analogy with those of 2. Nevertheless, analysis of MBr1 binding to these compounds indicate that substitution of the acetamido group at C-2 with the ester group lowers the affinity, thus suggesting that the amide hydrogen atom of 2 is involved in intermolecular interactions with the MBr1 antibody.Pubblicazioni consigliate
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