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Beilstein J. Org. Chem. 2017, 13, 1999–2009, doi:10.3762/bjoc.13.196
Graphical Abstract
Figure 1: (a) Structures of cell-membrane glycerophospholpids with a common asymmetric 1,2-diacyl-sn-glycerol...
Scheme 1: The four 1,2-dipalmitoyl-sn-glycerols 1–4 examined in this study.
Figure 2: 1H NMR spectra of 1,2-dipalmitin (3) in CDCl3 after partial isomerization into the 1,3-isomer. (a) ...
Figure 3: Fractional populations (%) of the three staggered conformers around the sn-1,2 C–C single bond in 1...
Scheme 2: Structures of glycerophospholipids with a common structural skeleton of 1,2-dipalmitoyl-sn-glycerol...
Figure 4: Partial 1H NMR spectrum of 4 in a mixture of CDCl3 and methanol-d4 (C/M = 10:1, v/v).
Figure 5: Linear relation between the helical disparity (%) and gt(+) population (%) as observed for the heli...
Figure 6: An empirical diagram showing helical conformational properties around 1,2-diacyl moiety in asymmetr...
Scheme 3: Chirally 2H-labelled tripalmitins (1S)- and (1R)-1-[2H]-1 [23].
Beilstein J. Org. Chem. 2012, 8, 629–639, doi:10.3762/bjoc.8.70
Figure 1: Absolute chemical structures of M. fermentans α-glycolipid antigens, GGPL-I and GGPl-III (GGPL: Gly...
Scheme 1: An established synthetic pathway to α-glycosyl-sn-glycerols 4a and 5a. A reagent combination of CBr4...
Scheme 2: Syntheses of GGPL-I homologue I-a and its isomer I-b. Conditions: (a) K2CO3, CH3OH; (b) cesium palm...
Figure 2: 1H NMR spectra of I-a and I-b (500 MHz, 25 °C, CDCl3/CD3OD 10:1). The assignment of sn-glycerol met...
Figure 3: Distributions of gg, gt and tg-conformers in 3-substituted sn-glycerols at 11 mM in solutions of CD...
Figure 4: Distributions of gg, gt and tg-conformers in 1-substituted sn-glycerols. In these sn-isomers, Φ1 an...
Figure 5: A common conformational property of GGPL-I and DPPC. The tail lipid moiety favors two gauche-confor...