352432-46-3Relevant articles and documents
New Disaccharide-Based Ether Lipids as SK3 Ion Channel Inhibitors
Berthe, Wilfried,Sevrain, Charlotte M.,Chant?me, Aurélie,Bouchet, Ana Maria,Gueguinou, Maxime,Fourbon, Yann,Potier-Cartereau, Marie,Haelters, Jean-Pierre,Couthon-Gourvès, Hélène,Vandier, Christophe,Jaffrès, Paul-Alain
, p. 1531 - 1539 (2016)
The SK3 potassium channel is involved in the development of bone metastasis and in the settlement of cancer cells in Ca2+-rich environments. Ohmline, which is a lactose-based glycero-ether lipid, is a lead compound that decreases SK3 channel activity and consequently limits the migration of SK3-expressing cells. Herein we report the synthesis of three new ohmline analogues in which the connection of the disaccharide moieties (1→6 versus 1→4) and the stereochemistry of the glycosyl linkage was studied. Compound 2 [3-(hexadecyloxy)-2-methoxypropyl-6-O-α-d-glucopyranosyl-β-d-galactopyranoside], which possesses an α-glucopyranosyl-(1→6)-β-galactopyranosyl moiety, was found to decrease SK3 current amplitude (70 % inhibition at 10 μm), displace SK3 protein outside caveolae, and decrease constitutive Ca2+entry (50 % inhibition at 300 nm) and SK3-dependent cell migration (30 % at 300 nm) at a level close to that of the benchmark compound ohmline. Compound 2, which decreases the activity of SK3 channel (but not SK2 channel), is a new drug candidate to reduce cancer cell migration and to prevent bone metastasis.
Synthesis and structural characterization of three unique helicobacter pylori a-cholesteryl phosphatidyl glucosides
Nguyen, Huy Q.,Davis, Ryan A.,Gervay-Hague, Jacquelyn
, p. 13400 - 13403 (2014)
Steryl glycosides produced by bacteria play important biological roles in the evasion and modulation of host immunity. Step-economical syntheses of three cholesteryl-6-Ophosphatidyl-α-d-glucopyranosides (αCPG) unique to Helicobacter pylori have been achie
Efficient Syntheses of β-Cyanosugars Using Glycosyl Iodides Derived from Per-O-silylated Mono- and Disaccharides
Bhat, Abhijit S.,Gervay-Hague, Jacquelyn
, p. 2081 - 2084 (2001)
Reported herein is a general method for the efficient syntheses of a variety of β-cyano glycosides through the activation of per-O-trimethylsilyl glycosides with TMSI to form α-glycosyl iodides, which undergo SN2-type displacement when treated with tetrabutylammonium cyanide. The cyanoglycosides were reduced under mild conditions using NaBH4 in the presence of catalytic CoCl2(H2O)6 in THF/H2O to give the corresponding aminomethyl glycosides.
Expeditious Synthesis of Ieodoglucomides A and B from the Marine-Derived Bacterium Bacillus licheniformis
Podilapu, Ananda Rao,Emmadi, Madhu,Kulkarni, Suvarn S.
, p. 3230 - 3235 (2018/07/06)
We report the total synthesis of ieodoglucomides A and B. The key steps of the synthesis are a glycosyl-iodide-mediated β-stereoselective glycosylation without neighbouring-group participation, a regioselective acylation, and a Grubbs cross-metathesis reaction. The short and efficient synthesis involves 11 steps, with 38–40 % overall yield.
