Synthesis and mesomorphic properties of glycosyl dialkyl- and diacyl-glycerols bearing saturated, unsaturated and methyl branched fatty acid and fatty alcohol chains. Part I. Synthesis.
Glycosyl dialkyl- and diacyl-glycerols bearing saturated, unsaturated or chiral methyl branched chains in the tail and disaccharide and trisaccharide carbohydrate headgroups were synthesised. Standard procedures were used for the preparation of the educts and the glyco lipids: trichloracetimidate procedure for the preparation of long-chained compounds, glycosylation using the beta-peracetate and boron trifluoride etherate was successful for the preparation of lipids with a medium-alkyl chain length. Preparation of the ester was afforded in a multi-step synthesis according to published procedures. Thus, several lipids were synthesised in a few synthetic steps in good yields. The introduction of unsaturated or methyl branched chains lead to liquid crystallinity at ambient temperature, because these compounds will be used as model compounds for biological systems. The biophysical properties of these compounds will be reported in a following paper.
Milkereit
Götz
G
Institute of Organic Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, 20146 Hamburg, Germany.
Gerber
Sven
S
Brandenburg
Klaus
K
Morr
Michael
M
Vill
Volkmar
V
D000215:Acylation; D000478:Alkylation; D001672:Biocompatible Materials / Q000032:analysis / Q000138:chemical synthesis; D003460:Crystallization / Q000379:methods*; D005227:Fatty Acids / Q000032:analysis* / Q000138:chemical synthesis*; D005233:Fatty Alcohols / Q000032:analysis* / Q000138:chemical synthesis*; D005990:Glycerol / Q000032:analysis* / Q000138:chemical synthesis*; D008968:Molecular Conformation; D044367:Phase Transition
D001672:Biocompatible Materials; D005227:Fatty Acids; D005233:Fatty Alcohols; D005990:Glycerol