Synthesis and mesogenic properties of a Y-shaped glyco-glycero-lipid.
We synthesised a new glyco-glycero-lipid [1,3-di-O-(beta-D-glucopyranosyl)-2-deoxy-2-amino-N-palmitoyl-sn-glycerol] with a Y-shaped structure bearing two sugar head groups and only one fatty acid chain. Instead of an ester linkage between the glycerol and the fatty acid an amido function was introduced. The mesogenic properties were investigated using polarising microscopy and are discussed with respect to similar compounds. The lyotropism was measured using the contact preparation method and small-angle neutron-scattering.
Milkereit
G
G
Institute of Organic Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, 20146 Hamburg, Germany.
Garamus
V M
VM
Veermans
K
K
Willumeit
R
R
Vill
V
V
D000577:Amides / Q000737:chemistry; D002241:Carbohydrates / Q000737:chemistry; D004952:Esters / Q000737:chemistry; D005227:Fatty Acids / Q000737:chemistry; D005990:Glycerol / Q000737:chemistry*; D006017:Glycolipids / Q000138:chemical synthesis*; D006031:Glycosylation; D008560:Membrane Fluidity; D008567:Membranes, Artificial; D008859:Microscopy, Polarization; D012542:Scattering, Radiation; D013329:Structure-Activity Relationship; D014867:Water / Q000737:chemistry
C496787:1,3-di-O-(beta-D-glucopyranosyl)-2-deoxy-2-amino-N-palmitoyl-sn-glycerol; D000577:Amides; D002241:Carbohydrates; D004952:Esters; D005227:Fatty Acids; D006017:Glycolipids; D008567:Membranes, Artificial; D014867:Water; D005990:Glycerol