Syntheses of an α-d-Gal-(1→6)-β-d-Gal diglyceride, as lipase substrate
| Autor: | Dominique Lafont, Paul Boullanger, Francine Ferrato, Frédéric Carrière |
|---|---|
| Přispěvatelé: | Laboratoire de Chimie Organique (LCO), Institut National des Sciences Appliquées de Lyon (INSA Lyon), Université de Lyon-Institut National des Sciences Appliquées (INSA)-Université de Lyon-Institut National des Sciences Appliquées (INSA), Enzymologie interfaciale et de physiologie de la lipolyse (EIPL), Centre National de la Recherche Scientifique (CNRS)-Aix Marseille Université (AMU), Aix Marseille Université (AMU)-Centre National de la Recherche Scientifique (CNRS) |
| Rok vydání: | 2006 |
| Předmět: |
Glycosylation
Stereochemistry Biochemistry Substrate Specificity Analytical Chemistry law.invention Diglycerides chemistry.chemical_compound Glycolipid law Galactolipase Diglyceride Lipase Digalactosyldiglyceride (DGDG) Molecular Structure biology [CHIM.ORGA]Chemical Sciences/Organic chemistry Organic Chemistry Substrate (chemistry) General Medicine chemistry Yield (chemistry) Recombinant DNA biology.protein Glycolipids |
| Zdroj: | Carbohydrate Research Carbohydrate Research, Elsevier, 2006, 341 (6), pp.695-704. ⟨10.1016/j.carres.2006.01.021⟩ Carbohydrate Research, 2006, 341 (6), pp.695-704. ⟨10.1016/j.carres.2006.01.021⟩ |
| ISSN: | 0008-6215 |
| DOI: | 10.1016/j.carres.2006.01.021 |
| Popis: | Two different routes were explored to afford 3-O-(6-O-alpha-D-galactopyranosyl-beta-D-galactopyranosyl)-1,2-di-O-dodecanoyl-sn-glycerol. In the first one, the key step was the glycosylation of the 3-O-(2,3,4-tri-O-benzyl-beta-D-galactopyranosyl)-1,2-O-isopropylidene-sn-glycerol acceptor with 2-pyridyl 2,3,4,6-tetra-O-benzyl-1-thio-beta-D-galactopyranoside as the donor. In the second one, the key step was the coupling of 2,3,4-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-benzyl-alpha-D-galactopyranosyl)-D-galactopyranosyl trichloroacetimidate donor with 1,2-O-isopropylidene-sn-glycerol. Even though the number of steps was the same in both pathways, the first one afforded a better overall yield (12.4%) than the second one (6.5%). This eight-step synthesis allowed the preparation of the expected glycolipid, which was used as substrate for recombinant GPLRP2 galactolipase using the monomolecular film technique. |
| Databáze: | OpenAIRE |
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