Facile synthesis of stable lipid analogues possessing a range of alkyl groups: application to artificial glycolipids.
Efficient preparation of lipid analogues is described in which various long alkoxy chains and 2-hydroxyethyl group were covalently linked with benzoic acid derivatives. An alpha-mannopyranosyl group was stereoselectively introduced by the conventional imidate method into the terminal hydroxy group without any alternation of other moieties in a molecule. The resulting new glycoconjugates acted as models of natural glycolipids for protein-carbohydrate interactions.
Azefu
Yasuo
Y
Department of Bioscience and Biotechnology, Faculty of Science and Engineering, Ritsumeikan University, Kusatsu, Shiga, Japan.
Tamiaki
Hitoshi
H
Sato
Reiko
R
Toma
Kazunori
K
D000818:Animals; D001565:Benzoates / Q000737:chemistry; D003208:Concanavalin A / Q000378:metabolism; D006001:Glycoconjugates / Q000138:chemical synthesis / Q000737:chemistry; D006017:Glycolipids / Q000138:chemical synthesis* / Q000737:chemistry; D007700:Kinetics; D008055:Lipids / Q000138:chemical synthesis / Q000737:chemistry; D008081:Liposomes / Q000737:chemistry; D008358:Mannose / Q000737:chemistry; D008958:Models, Molecular; D011485:Protein Binding; D012276:Ricin / Q000378:metabolism; D012710:Serum Albumin, Bovine / Q000378:metabolism; D013329:Structure-Activity Relationship
D001565:Benzoates; D006001:Glycoconjugates; D006017:Glycolipids; D008055:Lipids; D008081:Liposomes; D003208:Concanavalin A; D012710:Serum Albumin, Bovine; D012276:Ricin; D008358:Mannose