Title : Syntheses of an alpha-D-Gal-(1-->6)-beta-D-Gal diglyceride, as lipase substrate - Lafont_2006_Carbohydr.Res_341_695 |
Author(s) : Lafont D , Carriere F , Ferrato F , Boullanger P |
Ref : Carbohydr Res , 341 :695 , 2006 |
Abstract :
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-galact opyranosyl 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. |
PubMedSearch : Lafont_2006_Carbohydr.Res_341_695 |
PubMedID: 16458274 |
Substrate | DGDG |
Lafont D, Carriere F, Ferrato F, Boullanger P (2006)
Syntheses of an alpha-D-Gal-(1-->6)-beta-D-Gal diglyceride, as lipase substrate
Carbohydr Res
341 :695
Lafont D, Carriere F, Ferrato F, Boullanger P (2006)
Carbohydr Res
341 :695