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. 2013 Nov 1;18(11):13546-73.
doi: 10.3390/molecules181113546.

Synthesis and thermotropic phase behavior of four glycoglycerolipids

Wouter F J Hogendorf  1 , Vivien Jagalski, Thomas G Pomorski, Mikael Bols, Marité Cárdenas, Christian M Pedersen
Affiliations

Synthesis and thermotropic phase behavior of four glycoglycerolipids

Wouter F J Hogendorf et al. Molecules. .

Abstract

Four glycoglycerolipids with different head groups have been synthesized and their physicochemical properties studied. The lengths of the head groups from a mono-saccharide to a trisaccharide, in addition to the anomeric stereochemistry for the smaller glycoglycerolipids, have been modified. The synthesis has been optimized to avoid glycerol epimerization and to allow up-scaling. The physicochemical properties of the glycoglycerolipids were studied and a strong de-mixing of the gel-phase, depending on the head-group, was observed.

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Figures

Scheme 1
Scheme 1
Synthesis of the gentiobiosyl donor 2 and its glycosylation with 1,2-O-cyclohexylidene glycerol.
Scheme 2
Scheme 2
Synthesis of gentiobiosyl building block 7.
Scheme 3
Scheme 3
Global deprotection to give the glycolipids 15 (β-diglycolipid) and 16 (β-triglycolipid).
Scheme 4
Scheme 4
Synthesis of pseudotetrasaccharide 10.
Scheme 5
Scheme 5
Synthesis of donor 12 [32] and its glycosylation with pseudotrisaccharide 8.
Figure 1
Figure 1
Glycolipids 17 (α-monoglycolipid) and 18 (β-monoglycolipid).
Figure 2
Figure 2
DSC thermograms for (1) DMPS/DMPC, (2) DMPS/DMPC/β-monoglycolipid 18, (3) DMPS/DMPC/α-monoglycolipid 17, (4) DMPS/DMPC/β-diglycolipid 15, (5) DMPS/DMPC/β-triglycolipid 16. Vesicles at the compositions given in Table 1.
Figure 3
Figure 3
Confocal scanning fluorescence microscopy images for giant unilamellar vesicles containing β-diglycolipid 15 at 22 °C (A) and 37 °C (B). Vesicles composed of DMPC/DMPS/5 labeled with 0.1% DiI C18 (green) and 0.1% DiIC18 (red) were prepared as described in the supporting information. Color merged images were shown.
See this image and copyright information in PMC

References

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