Synthesis of the Sda determinant and two analogous tetrasaccharides
| Popis souboru: | text/plain |
|---|---|
| ISSN: | 0008-6215 |
| Přístupová URL adresa: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::36780ec4b6045ff5ddbf706fe134a3e7 https://pubmed.ncbi.nlm.nih.gov/9163897 |
| Rights: | CLOSED |
| Přírůstkové číslo: | edsair.doi.dedup.....36780ec4b6045ff5ddbf706fe134a3e7 |
| Autor: | Johannes F.G. Vliegenthart, Johannis P. Kamerling, Paul B. van Seeventer |
| Rok vydání: | 1997 |
| Předmět: |
Glycan
Magnetic Resonance Spectroscopy Stereochemistry Molecular Sequence Data Oligosaccharides Biochemistry Mass Spectrometry Analytical Chemistry chemistry.chemical_compound Mucoproteins Glucosides Bromide Polysaccharides Uromodulin Carbohydrate Conformation Glycosyl Trisaccharide chemistry.chemical_classification biology Molecular Structure Organic Chemistry General Medicine Nuclear magnetic resonance spectroscopy Scheikunde Acceptor chemistry Carbohydrate Sequence Biological significance biology.protein Carbohydrate conformation Trisaccharides |
| Zdroj: | Carbohydrate research, 299(3), 181. Elsevier |
| ISSN: | 0008-6215 |
| Popis: | To contribute to the possibility of studying in greater detail the biological significance of Sda-containing glycans as occur in Tamm-Horsfall glycoprotein, the following three spacer-linked tetrasaccharides have been synthesized: the Sda determinant alpha-Neu p5Ac-(2-->3)-[beta- D-GalpNAc-(1-->4)]-beta-D-Galp-(1-->4)-beta-D-GlcpNAc-(1-->O)(CH2)5NH 2 (1), the Gal-analogue alpha-Neup5Ac-(2-->3)-[beta-D-Galp-(1-->4)]-beta-D-Galp-(1-->4) -beta-D-GlcpNAc-(1-->O)(CH2)5NH2 (2), and the GlcNAc-analogue alpha-Neup5Ac-(2-->3)-[beta-D-GlcpNAc-(1-->4)]- beta-D-Galp-(1-->4)-beta-D-GlcpNAc-(1-->O)(CH2)5NH2 (3). The general trisaccharide acceptor 5-azidopentyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy- D-glycero-alpha-D-galactonon-2-ulopyranosylonate)-(2-->3)-(2 ,6-di-O-benzyl- beta-D-galactopyranosyl)-(1-->4)-3,6-di-O- benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranoside was prepared, using methyl (phenyl 5- acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto- non- 2-ulopyranosid)- onate as the sialyl donor. For the syntheses of 1, 2, and 3 the glycosyl donors 3,4,6-tri-O- acetyl-2-deoxy-2-phthalimido-alpha-D-galactopyranosyl bromide, 2,3,4,6-tetra-O-acetyl-alpha-D- galactopyranosyl bromide, and 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido -beta-D-glucopyranosyl trichloroacetimidate, respectively, proved to be the most suitable. |
| Databáze: | OpenAIRE |
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