A comparative analysis of mono- and disaccharide benzyl fucopyranosides.
The syntheses and X-ray analyses of two fucopyranosides, the monosaccharide benzyl 3,4-di-O-acetyl-2-hydroxy-beta-D-fucopyranoside, C(17)H(22)O(7), and the disaccharide 1-benzyl O-(2,3-di-O-acetyl-4,6-O-benzylidene-beta-D-glucopyranosyl)-(1-->2)-3,4-O-isopropylidene-beta-D-fucopyranoside, C(33)H(40)O(12), are described. The different substituents induce small conformational changes on the fucopyranoside ring. However, the conformation of the benzyl group varies from (+)gauche for the monosaccharide to synperiplanar for the disaccharide.
Unidad Interdisciplinaria de Biotecnología IPN, Av Acueducto s/n Col. Barrio la Laguna Ticomán, CP 07340, México DF, Mexico.
Marco
M
Brito-Arias
Enrique
E
Durán-Páramo
Ignasi
I
Mata
Elies
E
Molins
D002236:Carbohydrate Conformation; D002241:Carbohydrates / Q000737:chemistry*; D008958:Models, Molecular
D002241:Carbohydrates