First synthesis of the 3'-sulfated Lewis(a) pentasaccharide, the most potent human E-selectin ligand so far.
Tri- and pentasaccharides of Lewis(a)-type, sulfated at position 3 of the outer galactose, have been prepared using the new 4-methoxybenzyl glycoside of N-acetylglucosamine 5 as starting material. The synthesis of the pentasaccharide 2 was achieved through a beta-stereoselective coupling of an alpha-trichloroacetimidate activated form of the N-acetamido protected trisaccharide 18 on to a 3',4'-unprotected lactose derivative.
Lubineau
A
A
Laboratoire de Chimie Organique Multifonctionnelle (URA CNRS 462), Institut de Chimie Moléculaire d'Orsay, Université de Paris-Sud, France.
Le Gallic
J
J
Lemoine
R
R
D002240:Carbohydrate Sequence; D015815:Cell Adhesion Molecules / Q000276:immunology / Q000378:metabolism*; D019040:E-Selectin; D006801:Humans; D007983:Lewis Blood Group Antigens / Q000737:chemistry* / Q000276:immunology / Q000378:metabolism; D008024:Ligands; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000378:metabolism; D013431:Sulfates / Q000138:chemical synthesis
D015815:Cell Adhesion Molecules; D019040:E-Selectin; D007983:Lewis Blood Group Antigens; D008024:Ligands; D009844:Oligosaccharides; D013431:Sulfates