Chemical synthesis of a hexasaccharide comprising the Lewisx determinant linked beta-(1-->6) to a linear trimannosyl core and the precursor pentasaccharide lacking fucose.
Phenyl 2,3,4-tri-O-acetyl-6-O-chloroacetyl-1-thio-alpha,beta-mannopyranoside (5) was condensed with benzyl O-(2,3,4-tri-O-benzyl-beta-D-mannopyranosyl)-(1-->6)-2,3,4-tri-O-benzyl- alpha-D- mannopyranoside (12) in the presence of NIS-triflic acid to give, after removal of the chloroacetyl group, the key intermediate, benzyl O-(2,3,4-tri-O-acetyl-alpha-D-mannopyranosyl)-(1-->6)-O-(2,3,4-tri-O-ben zyl- beta-D-mannopyranosyl)-(1-->6)-2,3,4-tri-O-benzyl-alpha-D-mannopyranosid e (14). A similar condensation of 6 and 7 with acceptor 14, followed by the removal of protecting groups, afforded 16 and 18, respectively. These compounds are expected to be useful in specificity studies of an antibody raised against a related, synthetic antigen that we are currently investigating.
Jain
R K
RK
Department of Gynaecologic Oncology, Roswell Park Cancer Institute, Buffalo, NY 14263, USA.
Matta
K L
KL
D015703:Antigens, CD / Q000737:chemistry; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D006801:Humans; D007202:Indicators and Reagents; D016256:Lewis X Antigen / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry*; D009904:Optical Rotation
D015703:Antigens, CD; D007202:Indicators and Reagents; D016256:Lewis X Antigen; D009844:Oligosaccharides