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New Highly Hydrophobic Lewis X Glycolipids: Synthesis and Monolayer Behaviour
Author(s) -
Esnault Jacques,
Mallet JeanMaurice,
Zhang Yongmin,
Sinaÿ Pierre,
Le Bouar Tugdual,
Pincet Frédéric,
Perez Éric
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200101)2001:2<253::aid-ejoc253>3.0.co;2-2
Subject(s) - chemistry , glycolipid , glycoconjugate , moiety , stereochemistry , monolayer , alkyl , glycosphingolipid , vesicle , organic chemistry , biochemistry , membrane
Two highly hydrophobic Lewis X glycolipids 2 and 3 were prepared. The glycoconjugate 2 was constructed in the following way: pentaerythrytol was used as a distributor on which three racemic phytol hydrophobic chains and a triethyleneglycol spacer β‐glycosylated with the pentasaccharide Gal (β 1−4)[Fuc (α 1−3)] GlcNAc (β 1−3) Gal (β 1−4) Glc were anchored. The glycoconjugate 3 was constructed in a similar way, the sugar moiety being the trisaccharide Gal (β 1−4)[Fuc (α 1−3)] GlcNAc, the so‐called Lewis X determinant. A triethyleneglycol spacer was used in order to introduce the mobility required for the study of single carbohydrate−carbohydrate interactions. Three phytyl chains increase the hydrophobicity of the lipid moiety compared to the natural ceramide glycolipid 1 . These glycolipids display a liquid‐expanded behaviour with a high compressibility in monolayer studies. These properties associated with a low solubility in water make them good candidates for the study of the interaction between two Lewis X functionalized vesicles.