194930-71-7Relevant articles and documents
Synthesis and liquid crystalline properties of mono-, di- and tri-O-alkyl pentaerythritol derivatives bearing tri-, di- or monogalactosyl heads: The effects of curvature of molecular packing on mesophase formation
Dumoulin, Fabienne,Lafont, Dominique,Huynh, Thai-Le,Boullanger, Paul,Mackenzie, Grahame,West, Jon J.,Goodby, John W.
, p. 5585 - 5600 (2007)
Self-organisation and self-assembly are critical to the stability of synthetic and biological membranes. Of particular importance is consideration of the packing arrangements of the various molecular species. Both phosphoand glycolipids can pack in ways in which curvature can be introduced into self-organised or self-assembled systems. For instance, it is known that the degree of curvature can affect the structures of any condensed phases that are formed. In this article we report on a systematic study in which we have varied the shapes of glycolipids and examined the condensed phases that they form. In doing so, we have also unified the shape dependency of lyotropic liquid crystals with those of thermotropic liquid crystals. In order to undertake this systematic study a range of different pentaerythritol derivatives was synthesized, which covers combinations of one to three alkyl chains of different lengths (6,7,9,10,11,12,14,16 carbon atoms) and three to one galactosyl heads. Monoand di-O-galactosyl derivatives were prepared directly by glycosylation of the corresponding alcohols using 2,3,4,6-tetra-O-benzoyl or acetyl-α-D- galactopyranosyl trichloroacetimidate or bromide as the donors; the tri-O-galactosyl derivatives were synthesized from O-alkyl-O-benzyl di-O-galactosyl pentaerythritol intermediates, followed by de-O-benzylation and glycosylation steps. All of the fully deprotected products were obtained by standard methods, and their self-organising and self-assembling properties examined.
Synthesis and interfacial behaviour of a gemini neoglycolipid
Chierici,Boullanger,Marron-Brignone,Morelis,Coulet
, p. 91 - 101 (1997)
A gemini neoglycolipid was synthezised from pentaerythritol as the central building block to which were coupled two lipid moieties (C16H33 alkyl chains). The subsequent glyosylation reaction with two carbohydrate units (β-D-GlcNAc) was achieved in acceptable yields which were, nevertheless, much lower than those obtained with the single-chain homologous derivatives. The behaviour of this neoglycolipid in monolayer was studied in details after spreading at an air/water interface. These molecules exhibit transition phases when the monolayer is compressed, revealing a similar behaviour to that of phospholipids. The behaviour of neoglycolipid 1 suggests a peculiar conformation at the air/water interface. This supramolecular arrangement might be taken as a model for molecular recognition of glycolipids in organized systems.
