70932-37-5Relevant articles and documents
Synthesis and applications of carbohydrate based chiral ionic liquids as chiral recognition agents and organocatalysts
Kaur, Nirmaljeet,Chopra, Harish Kumar
, (2019/11/26)
Chiral ionic liquids (CILs) have shown a wide range of applications in variety of domains in chemistry. Because of this, synthesis and applications of CILs have always been areas of interest for research in the last 20 years. Present work describes, the synthesis of six carbohydrate based chiral ionic liquids (CCILs) by following simple procedures and their applications. Structures of the CCILs were confirmed through various analytical techniques like NMR spectroscopy (1H, 13C, 11B, 31P, 19F), EI-MS, and polarimetry. Designed CCILs were tested as chiral recognising agents using sodium salt of Mosher's acid as model substrate through 19F NMR spectroscopy. Further, CCILs were used as organocatalyst in the enantioselective reduction of aromatic prochiral ketones to achieve corresponding chiral secondary alcohols.
Fluorescently labeled substrates for monitoring α1,3- fucosyltransferase IX activity
Lunau, Nathalie,Seelhorst, Katrin,Kahl, Stefanie,Tscherch, Kathrin,Stacke, Christina,Rohn, Sascha,Thiem, Joachim,Hahn, Ulrich,Meier, Chris
, p. 17379 - 17390 (2014/01/06)
Fucosylation is often the final process in glycan biosynthesis. The resulting glycans are involved in a variety of biological processes, such as cell adhesion, inflammation, or tumor metastasis. Fucosyltransferases catalyze the transfer of fucose residues from the activated donor molecule GDP-β-L-fucose to various acceptor molecules. However, detailed information about the reaction processes is still lacking for most fucosyltransferases. In this work we have monitored α1,3-fucosyltransferase activity. For both donor and acceptor substrates, the introduction of a fluorescent ATTO dye was the last step in the synthesis. The subsequent conversion of these substrates into fluorescently labeled products by α1,3-fucosyltransferases was examined by high-performance thin-layer chromatography coupled with mass spectrometry as well as dual-color fluorescence cross-correlation spectroscopy, which revealed that both fluorescently labeled donor GDP-β-L-fucose-ATTO 550 and acceptor N-acetyllactosamine-ATTO 647N were accepted by recombinant human fucosyltransferase IX and Helicobacter pylori α1,3- fucosyltransferase, respectively. Analysis by fluorescence cross-correlation spectroscopy allowed a quick and versatile estimation of the progress of the enzymatic reaction and therefore this method can be used as an alternative method for investigating fucosyltransferase reactions. Fucosyl transfer: Two substrates of α1,3-fucosyltransferase IX have been labeled with ATTO dyes to monitor the enzymatically catalyzed transfer of the sugar moiety (see figure). The labeled guanosine diphosphate-fucose derivative was prepared by using cycloSal technology. The successful transfer reaction was first proven by high-performance thin-layer chromatography coupled with mass spectrometry. Fluorescence cross-correlation spectroscopy proved to be a suitable method for monitoring the enzyme activity.
Synthesis from d-altrose of (5 R,6 R,7 R,8 S)-5,7-dihydroxy-8- hydroxymethylconidine and 2,4-dideoxy-2,4-imino-d-glucitol, azetidine analogues of swainsonine and 1,4-dideoxy-1,4-imino-d-mannitol
Araújo, Noelia,Jenkinson, Sarah F.,Martínez, R. Fernando,Glawar, Andreas F. G.,Wormald, Mark R.,Butters, Terry D.,Nakagawa, Shinpei,Adachi, Isao,Kato, Atsushi,Yoshihara, Akihide,Akimitsu, Kazuya,Izumori, Ken,Fleet, George W. J.
supporting information; experimental part, p. 4174 - 4177 (2012/10/23)
Ring closure of a 3,5-di-O-triflate derived from d-altrose with benzylamine allowed the formation of both monocyclic and bicyclic azetidine analogues of swainsonine.
