Syntheses of an alpha-D-Gal-(1-->6)-beta-D-Gal diglyceride, as lipase substrate.
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.
Lafont
Dominique
D
Laboratoire de Chimie Organique II, UMR CNRS 5181, Université Lyon 1, Bâtiment 308, 43 Bd du 11 Novembre 1918, F 69622 Villeurbanne, France.
Carrière
Frédéric
F
Ferrato
Francine
F
Boullanger
Paul
P
D004075:Diglycerides / Q000138:chemical synthesis* / Q000378:metabolism*; D006017:Glycolipids / Q000138:chemical synthesis* / Q000378:metabolism*; D008049:Lipase / Q000378:metabolism*; D015394:Molecular Structure; D013379:Substrate Specificity
C512145:3-O-(6-O-galactopyranosylgalactopyranosyl)-1,2-di-O-dodecanoylglycerol; D004075:Diglycerides; D006017:Glycolipids; D008049:Lipase