Synthesis of two analogues of the Sda determinant. Replacement of the sialic acid residue by a sulfate or a carboxymethyl group.
Two analogues of the Sda determinant tetrasaccharide have been synthesized in order to investigate the physiological role of this carbohydrate moiety. These saccharides, having two different anionic substitutes for the sialic acid residue, are: beta-D-GalpNAc-(1-->4)-3-O-SO3 H- beta-D-Galp-(1-->4)-beta-D-GlcpNAc-(1-->O)(CH2)5NH2 and beta-D-GalpNAc-(1-->4)-3-O- COOH-beta-D-Galp-(1-->4)-beta-D-GlcpNAc-(1-->O)(CH2)5NH2. 5-Azidopentyl (2,6-di-O- benzyl-beta-D-galactopyranosyl)-(1-->4)-3,6-di-O-benzyl-2-deoxy-2- phthalimido-beta-D-glucopyranoside served as a general building block. The trisaccharides were obtained after prior selective derivatization of HO-3' of the disaccharide derivative via a dibutyltin oxide mediated reaction, followed by coupling at HO-4' with 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-beta-D-galactopyranosyl trichloroacetimidate, and processing of the formed trisaccharide derivatives into their free forms.
van Seeventer
P B
PB
Bijvoet Center, Department of Bio-Organic Chemistry, Utrecht University, The Netherlands.
Corsten
M A
MA
Sanders
M P
MP
Kamerling
J P
JP
Vliegenthart
J F
JF
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002264:Carboxylic Acids / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D009088:Mucoproteins / Q000737:chemistry / Q000276:immunology; D019158:N-Acetylneuraminic Acid / Q000737:chemistry*; D009844:Oligosaccharides / Q000138:chemical synthesis*; D011134:Polysaccharides / Q000737:chemistry / Q000276:immunology; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013431:Sulfates / Q000138:chemical synthesis*; D058949:Uromodulin
D002264:Carboxylic Acids; D009088:Mucoproteins; D009844:Oligosaccharides; D011134:Polysaccharides; C106678:Sd(a) determinant; D013431:Sulfates; D058949:Uromodulin; D019158:N-Acetylneuraminic Acid