Synthesis and liquid-crystalline properties of novel archaeal diether-typeglycolipids possessing one or two furanosyl units

Archaeal diether-type analogues possessing one or two furanosyl polar head groups and methyl branched aliphatic moieties were synthesized by glycosyla tion of glycerolipids with pent-4-enyl 2,3,5,6-tetra-O-acetyl-D-glycofurano side as the donors. The products were shown to form thermotropic and lyotro pic liquid crystalline mesophases, tubules and vesicles. The self-assemblin g properties of the compounds prepared were found to be similar to those of naturally occurring materials, in that they exhibited columnar thermotropi c mesophases and hexagonal lyotropic phases. (C) 1998 Elsevier Science Ltd. All rights reserved.