Stereoselective total synthesis of tri- and tetrahexoside wheat flour ceramide.
The wheat glycosphingolipids, O-(beta-D-mannopyranosyl-[(1-->4)-O-(beta-D-mannopyranosyl)]n-O-(beta-D -glucopyranosyl)-(1-->1)-(2S,3S,4R)-4-hydroxy-N-tetracosanoylsphingan ine (n = 1 and 2), were stereoselectively synthesized. Silver silicate promoted glycosylation when 4-O-acetyl-2,3,6-tri-O-benzyl-alpha-D-mannopyranosyl bromide was used for elongating the glycan chains, which were latter coupled with the ceramide derivative by the trichloroacetimidate method.
Koike
K
K
College of Pharmacy, Nihon University, Chiba, Japan.
Mori
M
M
Ito
Y
Y
Nakahara
Y
Y
Ogawa
T
T
D002240:Carbohydrate Sequence; D002518:Ceramides / Q000138:chemical synthesis* / Q000737:chemistry; D006028:Glycosphingolipids / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D013237:Stereoisomerism; D014908:Triticum / Q000737:chemistry*
D002518:Ceramides; D006028:Glycosphingolipids