6984-43-6Relevant academic research and scientific papers
Synthesis of novel carbohydrate based pyridinium ionic liquids and cytotoxicity of ionic liquids for mammalian cells
Brietzke, Andreas,Eickner, Thomas,Jopp, Stefan,Kragl, Udo,Rei?, Melanie,Stein, Florian,Villinger, Alexander,Vogel, Christian
, p. 14299 - 14304 (2020/04/23)
The large pool of naturally occurring carbohydrates with their diversity in chirality and structure led to the idea of a systematic investigation of carbohydrate based ILs. To this end, we investigated the influence of different ether groups, mainly methyl or ethyl ether, on the secondary OH groups as well as different configurations on physical properties such as melting point, thermostability and especially the influence on cell toxicity. For this investigation we chose α- and β-methyl-, β-allyl- and β-phenyl d-glucopyranose as well as four 1-deoxy-pentoses. In order to be able to classify the results, more ionic liquids with different structural motives were examined for cytotoxicity. Here, we present data that confirm the biocompatibility of such ILs consisting of naturally occurring molecules or their derivatives. The synthesized carbohydrate based ILs were tested for their suitability as additives in coatings for medical applications such as drug-eluting balloons.
Visible Light Enables Aerobic Iodine Catalyzed Glycosylation
Krumb, Matthias,Lucas, Tobias,Opatz, Till
supporting information, p. 4517 - 4521 (2019/08/06)
A versatile protocol for light induced catalytic activation of thioglycosides using iodine as an inexpensive and readily available photocatalyst was developed. Oxygen serves as a green and cost-efficient terminal oxidant and irradiation is performed with a common household LED-bulb. The scope of this glycosylation protocol was investigated in the synthesis of O-glycosides with yields up to 95 %.
Anti-coagulation pentasaccharide and preparing method and medical application thereof
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Paragraph 0072-0077, (2019/01/23)
The invention relates to a synthesized pentasaccharide compound, salt thereof, and application of the pentasaccharide compound in preparing medicines for preventing and/or treating blood coagulation disorder related diseases.
Swapping Interface Contacts in the Homodimeric tRNA-Guanine Transglycosylase: An Option for Functional Regulation
Ehrmann, Frederik Rainer,Kalim, Jorna,Pfaffeneder, Toni,Bernet, Bruno,Hohn, Christoph,Sch?fer, Elisabeth,Botzanowski, Thomas,Cianférani, Sarah,Heine, Andreas,Reuter, Klaus,Diederich, Fran?ois,Klebe, Gerhard
supporting information, p. 10085 - 10090 (2018/08/06)
The enzyme tRNA-guanine transglycosylase, a target to fight Shigellosis, recognizes tRNA only as a homodimer and performs full nucleobase exchange at the wobble position. Active-site inhibitors block the enzyme function by competitively replacing tRNA. In
ANTI-CANCER AND SPLCE MODULATING COMPOUNDS AND METHODS
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Paragraph 0300; 0301; 0302, (2017/09/27)
There are provided inter alia stable anti-cancer compounds and splice modulators and methods of synthesis and use thereof.
A Carbohydrate-Derived Splice Modulator
Dhar, Sachin,La Clair, James J.,León, Brian,Hammons, Justin C.,Yu, Zhe,Kashyap, Manoj K.,Castro, Januario E.,Burkart, Michael D.
supporting information, p. 5063 - 5068 (2016/05/19)
Small-molecule splice modulators have recently been recognized for their clinical potential for diverse cancers. This, combined with their use as tools to study the importance of splice-regulated events and their association with disease, continues to fue
Carbene-mediated functionalization of the anomeric C-H bond of carbohydrates: Scope and limitations
Boultadakis-Arapinis, Mélissa,Prost, Elise,Gandon, Vincent,Lemoine, Pascale,Turcaud, Serge,Micouin, Laurent,Lecourt, Thomas
, p. 6052 - 6066 (2013/06/27)
Herein we investigate the scope and limitations of a new synthetic approach towards α- and β-ketopyranosides relying on the functionalization of the anomeric C-H bond of carbohydrates by insertion of a metal carbene. A key bromoacetate grafted at the 2-position is the cornerstone of a stereoselective glycosylation/diazotransfer/quaternarization sequence that makes possible the construction of a quaternary center with complete control of the stereochemistry. This sequence shows a good tolerance toward protecting groups commonly used in carbohydrate chemistry and gives rise to quaternary disaccharides with good efficiency. In the case of a disaccharide with a more restricted conformation, this functionalization process can be hampered by the steric demand next to the targeted anomeric position. In addition, the formation of transient orthoesters during the glycosylation step may also reduce the overall efficiency of the synthetic sequence. Copyright
Defining oxyanion reactivities in base-promoted glycosylations
Matwiejuk, Martin,Thiem, Joachim
supporting information; experimental part, p. 8379 - 8381 (2011/09/14)
Saccharide oxyanions obtained by base treatment could be employed in glycosylation to give oligosaccharides with high stereo- and regioselectivities.
Synthesis of 2,3,4,5-tetra-O-methyl-D-glucono-1,6-lactone as a monomer for the preparation of copolyesters
Molina Pinilla, Inmaculada,Bueno Martinez, Manuel,Galbis, Juan A.
, p. 549 - 555 (2007/10/03)
2,3,4,5-Tetra-O-methyl-D-glucono-1,6-lactone has been prepared as a crystalline compound in acceptable yield by two different routes. An initial assay of copolymerization with L-lactide by ring-opening polymerization was carried out. The incorporation of the carbohydrate monomer into the polymer chain was about 2%.
Enolic ortho esters. VII* involvement of magnesium halides as lewis acids in the reaction of grignard reagents with 1,6-dideoxy-1,1-ethylenedioxy-2,3,4-tri-o-methyl-d-xylo-hex-5-enopyranose and its 6-phenyl derivative: A correction
Collins, David J.,Hibberd, Angus I.,Skelton, Brian W.,White, Allan H.
, p. 681 - 694 (2007/10/03)
The known aldehyde methyl 2,3,4-tri-O-methyl-α-D-gluco-hexodialdo-1,5-pyranoside (9) was converted in eight steps into the 6-phenyl glucose-derived enolic ortho ester (Z)-1,6-dideoxy-1,1-ethylenedioxy-2,3,4-tri-O-methyl-6-phenyl-D-xylo-hex-5- enopyranose
