TY - JOUR
T1 - Oligosaccharides Related to Tumor‐Associate Antigens. Part 2. Conformational analysis of the trisaccharide α‐L‐Fucp‐(1→2)‐β‐D‐Galp‐(1→3)‐β‐D‐GalpNAc, epitope structure recognized by the MBr1 antibody
AU - Toma, Lucio
AU - Ciuffreda, Pierangela
AU - Colombo, Diego
AU - Ronchetti, Fiamma
AU - Lay, Luigi
AU - Panza, Luigi
PY - 1994/5/11
Y1 - 1994/5/11
N2 - The conformational space of the trisaccharide α‐L‐Fuc‐(1→2)‐β‐ D‐Gal‐(1→3)‐β ‐D‐GalNAc‐1‐OPr (2) and of its component disaccharide moieties α ‐L‐Fuc‐(1→2)‐β ‐D‐Gal‐1‐OMe (3) and β ‐D‐Gal‐(1→3)‐β‐ D‐GalNAc‐1‐OPr (4) was investigated with the aid of molecular‐mechanics energy minimizations and molecular‐dynamics simulations. These calculations suggested the occurrence of two conformations for each compound characterized by different ϕ and Ψ glycosidic angles. However, 1H‐NMR investigation of D2O solutions of 2–4 indicated a sure preference for one of the two conformers with a contribution of the other one ranging from negligible to low.
AB - The conformational space of the trisaccharide α‐L‐Fuc‐(1→2)‐β‐ D‐Gal‐(1→3)‐β ‐D‐GalNAc‐1‐OPr (2) and of its component disaccharide moieties α ‐L‐Fuc‐(1→2)‐β ‐D‐Gal‐1‐OMe (3) and β ‐D‐Gal‐(1→3)‐β‐ D‐GalNAc‐1‐OPr (4) was investigated with the aid of molecular‐mechanics energy minimizations and molecular‐dynamics simulations. These calculations suggested the occurrence of two conformations for each compound characterized by different ϕ and Ψ glycosidic angles. However, 1H‐NMR investigation of D2O solutions of 2–4 indicated a sure preference for one of the two conformers with a contribution of the other one ranging from negligible to low.
UR - http://www.scopus.com/inward/record.url?scp=0028232010&partnerID=8YFLogxK
U2 - 10.1002/hlca.19940770310
DO - 10.1002/hlca.19940770310
M3 - Article
SN - 0018-019X
VL - 77
SP - 668
EP - 678
JO - Helvetica Chimica Acta
JF - Helvetica Chimica Acta
IS - 3
ER -