Synthesis of precursors for the dimeric 3-O-SO3Na Lewis X and Lewis A structures.
Stereoselective syntheses of 3-O-SO3Na-beta-Gal-(1-->4)-beta-GlcNAc- (1-->3)-beta-Gal-(1-->4)-GlcNAc-beta-OBn (15) and 3-O-SO3Na-beta-Gal-(1-->3)-beta-GlcNAc-(1-->3)-beta-Gal-(1-->3)- beta-GlcNAc-(1-->3)-beta-Gal-(1-->4)-Glc-beta-OBn (25) were accomplished through the use of two novel glycosyl donors, namely, ethyl O-(2,6-di-O-acetyl-3,4-O-isopropylidene-beta-D- galactopyranosyl)-(1-->4)-3-O-acetyl-2-deoxy-2-phthalimido-1-thio-6-O- trimethylacetyl-beta-D-glucopyranoside (8). and ethyl O-(2,6-di-O-acetyl-3,4-O-isopropylidene-beta-D-galactopyranosyl)- (1-->3)-4-O-acetyl-2-deoxy-2-phthalimido-1-thio-6-O-trimethylace tyl-beta-D-glucopyranoside (18).
Reddy
G V
GV
Department of Gynecologic Oncology, Roswell Park Cancer Institute, Buffalo, NY 14263, USA.
Jain
R K
RK
Locke
R D
RD
Matta
K L
KL
D018395:CA-19-9 Antigen; D002240:Carbohydrate Sequence; D005647:Fucosyltransferases / Q000378:metabolism; D005732:Gangliosides / Q000096:biosynthesis* / Q000737:chemistry; D006031:Glycosylation; D007983:Lewis Blood Group Antigens / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009844:Oligosaccharides / Q000096:biosynthesis* / Q000737:chemistry; D000080506:Sialyl Lewis X Antigen; D012799:Sialyltransferases / Q000378:metabolism; D015238:Sulfotransferases / Q000378:metabolism
D018395:CA-19-9 Antigen; D005732:Gangliosides; D007983:Lewis Blood Group Antigens; D009844:Oligosaccharides; D000080506:Sialyl Lewis X Antigen; C098451:benzyl O-(3-O-sulfo-galactopyranosyl)-1-3-(2-acetamido-2-deoxyglucopyranosyl)-1-3-galactopyranosyl-1-3-(2-acetamido-2-deoxyglucopyranosyl)-1-3-galactopyranosyl-1-4-glucopyranoside; C098450:benzyl O-(3-O-sulfogalactopyranosyl)-1-4-(2-acetamido-2-deoxyglucopyranosyl)-1-3-galactopyranosyl-(1-4)-2-acetamido-2-deoxyglucopyranoside; C064564:sialyl Le(a) ganglioside; D005647:Fucosyltransferases; D012799:Sialyltransferases; D015238:Sulfotransferases