Synthesis of two analogues of the Sda determinant. Replacement of the sialic acid residue by a sulfate or a carboxymethyl group
| Autor: | Johannis P. Kamerling, Paul B. van Seeventer, Marion P. Sanders, Johannes F.G. Vliegenthart, Michael A. Corsten |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 1997 |
| Předmět: |
Magnetic Resonance Spectroscopy
Stereochemistry Molecular Sequence Data Disaccharide Carboxylic Acids Oligosaccharides Spectrometry Mass Fast Atom Bombardment Biochemistry Analytical Chemistry chemistry.chemical_compound Residue (chemistry) Mucoproteins Polysaccharides Uromodulin Carbohydrate Conformation Tetrasaccharide Trisaccharide Sulfate Derivatization chemistry.chemical_classification Dibutyltin oxide Sulfates Organic Chemistry General Medicine Scheikunde N-Acetylneuraminic Acid Sialic acid chemistry Carbohydrate Sequence |
| Zdroj: | Carbohydrate research, 299(3), 171. Elsevier |
| ISSN: | 0008-6215 |
| Popis: | 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: β- d -Gal p NAc -(1 → 4)-3-O- SO 3 H -β- d -Gal p-(1 → 4)-β- d -Glc p NAc -(1 → O)( CH 2 ) 5 NH 2 and β- d -Gal p NAc -(1 → 4)-3-O- CH 2 COOH -β- d -Gal p-(1 → 4)-β- d -Glc p NAc -(1 → 0) (CH 2 ) 5 NH 2 . 5-Azidopentyl (2,6- di -O- benzyl -β- d -galactopyranosyl )-(1 → 4)-3,6- di -O- benzyl -2- deoxy -2- phthalimido -β- 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 -β- d - galactopyranosyl trichloroacetimidate, and processing of the formed trisaccharide derivatives into their free forms. Two analogues of the Sda determinant tetrasaccharide have been synthesized aimed at the investigation of the physiological role of this carbohydrate moiety. These saccharides, having two different anionic substitutes for the sialic acid residue, are; β- d -Gal p NAC -(1 → 4)-3-O- SO 3 H -β- d -Gal p-(1 → 4)-β- d -Glc p NAC -(1 → O ) (CH 2 ) 5 NH 2 and β- d -Gal p NAC -(1 → 4)-3-O- CH 2 COOH -β- d -Gal p-(1 → 4)-β- d -Glc p NAC -(1 → O ) (CH 2 ) 5 NH 2 . |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Full Text from ScienceDirect