14687-15-1Relevant articles and documents
IR-spectral signatures of aromatic-sugar complexes: Probing carbohydrate-protein interactions
Screen, James,Stanca-Kaposta, E. Cristina,Gamblin, David P.,Liu, Bo,Macleod, Neil A.,Snoek, Lavina C.,Davis, Benjamin G.,Simons, John P.
, p. 3644 - 3648 (2007)
(Figure Presented) Key interactions: Sugar-arene complexes have been created in molecular-beam experiments and observed by IR ion-dip spectroscopy in the gas phase. These complexes are powerful models of the selective recognition seen in protein-sugar complexes, for example between the galactose-specific lectin from Artocarpus hirsute and MeGal (see picture).
-
Lloyd,Forrester
, p. 430 (1971)
-
Modular Total Synthesis and Cell-Based Anticancer Activity Evaluation of Ouabagenin and Other Cardiotonic Steroids with Varying Degrees of Oxygenation
Khatri, Hem Raj,Bhattarai, Bijay,Kaplan, Will,Li, Zhongzheng,Curtis Long, Marcus John,Aye, Yimon,Nagorny, Pavel
supporting information, p. 4849 - 4860 (2019/03/26)
A Cu(II)-catalyzed diastereoselective Michael/aldol cascade approach is used to accomplish concise total syntheses of cardiotonic steroids with varying degrees of oxygenation including cardenolides ouabagenin, sarmentologenin, 19-hydroxysarmentogenin, and 5-epi-panogenin. These syntheses enabled the subsequent structure activity relationship (SAR) studies on 37 synthetic and natural steroids to elucidate the effect of oxygenation, stereochemistry, C3-glycosylation, and C17-heterocyclic ring. Based on this parallel evaluation of synthetic and natural steroids and their derivatives, glycosylated steroids cannogenol-l-α-rhamnoside (79a), strophanthidol-l-α-rhamnoside (92), and digitoxigenin-l-α-rhamnoside (97) were identified as the most potent steroids demonstrating broad anticancer activity at 10-100 nM concentrations and selectivity (nontoxic at 3 μM against NIH-3T3, MEF, and developing fish embryos). Further analyses indicate that these molecules show a general mode of anticancer activity involving DNA-damage upregulation that subsequently induces apoptosis.
Synthesis of Deoxyglycosides by Desulfurization under UV Light
Ge, Jian-Tao,Li, Ying-Ying,Tian, Jun,Liao, Rong-Zhen,Dong, Hai
, p. 7008 - 7014 (2017/07/15)
This study was performed to develop a highly efficient method whereby desulfurization could be completed in 0.5 h under ultraviolet light, at room temperature, and in the presence of trialkylphosphine. Using this method, deoxyglycosides could be produced from sulfur-containing glycosides in almost quantitative yields. The much higher reactivity of desulfurization with triethylphosphine versus that with triethylphosphite is also discussed.
Catalytic and regioselective oxidation of carbohydrates to synthesize keto-sugars under mild conditions
Muramatsu, Wataru
, p. 4846 - 4849 (2015/04/27)
A new catalytic and regioselective approach for the synthesis of keto-sugars is described. An organotin catalyst, Oc2SnCl2, in the presence of trimethylphenylammonium tribromide ([TMPhA]+Br3-) accelerates the regioselective oxidation at the axial -OH group of 1,2-diol moieties in galactopyranosides. The reaction conditions can also be used for the regioselective oxidation of various carbohydrates.
