Application of the anomeric samarium route for the convergent synthesis of the C-linked trisaccharide alpha-D-Man-(1-->3)-[alpha-D-Man-(1-->6)]-D-Man and the disaccharides alpha-D-Man-(1-->3)-D-Man and alpha-D-Man-(1-->6)-D-Man.
| Autoři: | Mikkelsen LM; Department of Chemistry, University of Aarhus, Langelandsgade 140, 8000 Aarhus C, Denmark., Krintel SL, Jiménez-Barbero J, Skrydstrup T |
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| Zdroj: | The Journal of organic chemistry [J Org Chem] 2002 Sep 06; Vol. 67 (18), pp. 6297-308. |
| Způsob vydávání: | Journal Article; Research Support, Non-U.S. Gov't |
| Jazyk: | English |
| Informace o časopise: | Publisher: American Chemical Society Country of Publication: United States NLM ID: 2985193R Publication Model: Print Cited Medium: Print ISSN: 0022-3263 (Print) Linking ISSN: 00223263 NLM ISO Abbreviation: J Org Chem Subsets: MEDLINE |
| Imprint Name(s): | Publication: Columbus Oh : American Chemical Society Original Publication: Easton, Pa. [etc.] |
| Výrazy ze slovníku MeSH: | Combinatorial Chemistry Techniques*, Disaccharides/*chemical synthesis , Mannosides/*chemical synthesis , Samarium/*chemistry , Trisaccharides/*chemical synthesis, Carbohydrate Conformation ; Carbohydrate Sequence ; Catalysis ; Glycosides/chemical synthesis ; Glycosides/chemistry ; Glycosylation ; Mannose-Binding Lectin/chemistry ; Molecular Sequence Data ; Nuclear Magnetic Resonance, Biomolecular/methods ; Oligosaccharides, Branched-Chain/chemistry ; Stereoisomerism |
| Abstrakt: | Studies are reported on the assembly of the branched C-trisaccharide, alpha-D-Man-(1-->3)-[alpha-D-Man-(1-->6)]-D-Man, representing the core region of the asparagine-linked oligosaccharides. The key step in this synthesis uses a SmI(2)-mediated coupling of two mannosylpyridyl sulfones to a C3,C6-diformyl branched monosaccharide unit, thereby assembling all three sugar units in one reaction and with complete stereocontrol at the two anomeric carbon centers. Subsequent tin hydride-based deoxygenation followed by a deprotection step produces the target C-trimer. In contrast to many of the other C-glycosylation methods, this approach employes intact carbohydrate units as C-glycosyl donors and acceptors, which in many instances parallels the well-studied O-glycosylation reactions. The synthesis of the C-disaccharides alpha-D-Man-(1-->3)-D-Man and alpha-D-Man-(1-->6)-D-Man is also described, they being necessary for the following conformational studies of all three carbohydrate analogues both in solution and bound to several mannose-binding proteins. |
| Substance Nomenclature: | 0 (Disaccharides) 0 (Glycosides) 0 (Man-(1-3)-(Man-(1-6))-Man) 0 (Mannose-Binding Lectin) 0 (Mannosides) 0 (Oligosaccharides, Branched-Chain) 0 (Trisaccharides) 0 (alpha-D-Man-(1-3)-D-Man) 0 (alpha-D-Man-(1-6)-D-Man) 42OD65L39F (Samarium) |
| Entry Date(s): | Date Created: 20020831 Date Completed: 20030404 Latest Revision: 20190710 |
| Update Code: | 20240829 |
| DOI: | 10.1021/jo020339z |
| PMID: | 12201747 |
| Autor: | Mikkelsen LM; Department of Chemistry, University of Aarhus, Langelandsgade 140, 8000 Aarhus C, Denmark., Krintel SL, Jiménez-Barbero J, Skrydstrup T |
| Jazyk: | angličtina |
| Zdroj: | The Journal of organic chemistry [J Org Chem] 2002 Sep 06; Vol. 67 (18), pp. 6297-308. |
| DOI: | 10.1021/jo020339z |
| Abstrakt: | Studies are reported on the assembly of the branched C-trisaccharide, alpha-D-Man-(1-->3)-[alpha-D-Man-(1-->6)]-D-Man, representing the core region of the asparagine-linked oligosaccharides. The key step in this synthesis uses a SmI(2)-mediated coupling of two mannosylpyridyl sulfones to a C3,C6-diformyl branched monosaccharide unit, thereby assembling all three sugar units in one reaction and with complete stereocontrol at the two anomeric carbon centers. Subsequent tin hydride-based deoxygenation followed by a deprotection step produces the target C-trimer. In contrast to many of the other C-glycosylation methods, this approach employes intact carbohydrate units as C-glycosyl donors and acceptors, which in many instances parallels the well-studied O-glycosylation reactions. The synthesis of the C-disaccharides alpha-D-Man-(1-->3)-D-Man and alpha-D-Man-(1-->6)-D-Man is also described, they being necessary for the following conformational studies of all three carbohydrate analogues both in solution and bound to several mannose-binding proteins. |
| Databáze: | MEDLINE |
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