Unusual lactam formation occurring in the synthesis of a biotinylated T-antigen-serine derivative.
Synthesis of the biotinylated T-antigens, linked to a serine by an alpha (7 alpha) or a beta (7 beta) 2-acetamido-2-deoxy-D-galactoside bond, is described. These derivatives were needed for the detection of a specific endogenous lectin at the surface and/or on the migration pathway of melanoma cells. In the course of the synthesis, an unusual lactam formation was observed with the beta anomer of the azido-disaccharide 5 beta.
Bay
S
S
Institut Pasteur, Département de Biochimie et Génétique Moléculaire, Paris, France.
Berthier-Vergnes
O
O
Biberovic
V
V
Cantacuzène
D
D
D000957:Antigens, Viral, Tumor / Q000737:chemistry*; D019921:Biotinylation; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D007769:Lactams / Q000737:chemistry; D037102:Lectins / Q000032:analysis; D015335:Molecular Probes; D008969:Molecular Sequence Data; D012694:Serine / Q000737:chemistry*
D000957:Antigens, Viral, Tumor; D007769:Lactams; D037102:Lectins; D015335:Molecular Probes; D012694:Serine