20379-61-7Relevant academic research and scientific papers
UDP-GlcNAc Analogues as Inhibitors of O-GlcNAc Transferase (OGT): Spectroscopic, Computational, and Biological Studies
Ghirardello, Mattia,Perrone, Daniela,Chinaglia, Nicola,Sádaba, David,Delso, Ignacio,Tejero, Tomas,Marchesi, Elena,Fogagnolo, Marco,Rafie, Karim,van Aalten, Daan M. F.,Merino, Pedro
supporting information, p. 7264 - 7272 (2018/05/04)
A series of glycomimetics of UDP-GlcNAc, in which the β-phosphate has been replaced by either an alkyl chain or a triazolyl ring and the sugar moiety has been replaced by a pyrrolidine ring, has been synthesized by the application of different click-chemistry procedures. Their affinities for human O-GlcNAc transferase (hOGT) have been evaluated and studied both spectroscopically and computationally. The binding epitopes of the best ligands have been determined in solution by means of saturation transfer difference (STD) NMR spectroscopy. Experimental, spectroscopic, and computational results are in agreement, pointing out the essential role of the binding of β-phosphate. We have found that the loss of interactions from the β-phosphate can be counterbalanced by the presence of hydrophobic groups at a pyrroline ring acting as a surrogate of the carbohydrate unit. Two of the prepared glycomimetics show inhibition at a micromolar level.
Study of aryl triazoles for absolute configuration determination
Tejera, Sara,Dorta, Rosa L.,Vázquez, Jesús T.
, p. 896 - 909 (2016/09/02)
A variety of chiral mono- and di-1,4-disubstituted 1,2,3-triazoles were synthesized by CuAAC ‘click chemistry’ as model compounds and their spectroscopic properties characterized. The UV and CD studies of these compounds showed that 4-substituted aryl tri
Protecting group free synthesis of urea-linked glycoconjugates: Efficient synthesis of β-urea glycosides in aqueous solution
Ichikawa, Yoshiyasu,Minami, Takahiro,Kusaba, Shohei,Saeki, Nobuyoshi,Tonegawa, Yuta,Tomita, Yumiko,Nakano, Keiji,Kotsuki, Hiyoshizo,Masuda, Toshiya
, p. 3924 - 3931 (2014/06/09)
A method for the protecting group free synthesis of β-urea-linked glycoconjugates has been developed. The one step process, involving reactions between urea and d-glucose, N-acetyl-d-glucosamine or d-xylose in acidic aqueous solution, furnishes the corresponding β-urea glycosides in modest yields. This simple and efficient procedure is applicable to the synthesis of β-urea tethered amino acid-carbohydrate conjugates. This journal is the Partner Organisations 2014.
Click chemistry: An efficient synthesis of heterocycles substituted with steroids, saponins, and digitalis analogues
Deobald, Anna M.,Camargo, Leandro R. S.,Alves, Diego,Zukerman-Schpector, Julio,Correa, Arlene G.,Paixao, Marcio W.
supporting information; scheme or table, p. 4003 - 4010 (2012/01/05)
The copper-catalyzed azide-alkyne cycloaddition (CuAAC) has been used for the construction of 1,2,3-triazole containing steroids in good to excellent yields. Combination of propargylic glycosides and steroidal azides as reaction partner allowed the synthesis of a privileged class of natural product analogues. The versatility of this protocol makes this chemistry a useful attractive approach for the synthesis of target molecules. Georg Thieme Verlag Stuttgart · New York.
Synthesis and biological activity of glycosyl-1H-1,2,3-triazoles
Slamova, Kristyna,Marhol, Petr,Bezouska, Karel,Lindkvist, Lise,Hansen, Signe G.,Kren, Vladimir,Jensen, Henrik H.
supporting information; experimental part, p. 4263 - 4265 (2010/08/22)
Glycosyl 1,2,3-triazoles with α-d-gluco, β-d-gluco, α-d-galacto, β-d-galacto and β-2-acetamido-2-deoxygluco (GlcNAc) stereochemistry were prepared by reaction of the corresponding azides with vinyl acetate under microwave irradiation. The deprotected glucosyl and galactosyl triazoles did not display inhibitory activity against the tested glycosidases at 1 mM. Of the four fungal glycosidases evaluated, GlcNAc-triazole was found to be hydrolyzed by Talaromyces flavus CCF 2686 β-N-acetylhexosaminidase. β-GlcNAc-triazole was furthermore established to act as a strong ligand of rat and human natural killer cell activating receptors.
2,3,4,6-Tetra-O-acetyl-α- d-gluco-pyranosyl azide
Dedola, Simone,Nepogodiev, Sergey A.,Hughes, David L.,Field, Robert A.
experimental part, p. o445-o446 (2009/04/13)
The CuI-catalysed 1,3-dipolar cyclo-addition of an azide and a terminal alkyne is becoming an increasingly popular tool for synthetic chemists. This is the most representative of the so-called click reactions and it is used to generate 1,4-di-substituted triazoles in high yield. During studies on such cyclo-addition reactions, a reduced reactivity of an -glucosyl azide with respect to the corresponding Β-anomer was observed. With the aim of understanding this phenomenon, the structure of the title compound, C14H19N3O9, has been determined at 140 K. The glucopyranosyl ring appears in a regular 4 C 1 chair conformation with all the substituents in equatorial positions, except for the anomeric azide group, which adopts an axial orientation. The observed bond lengths are consistent with a strong anomeric effect, which is reflected in a change in dipolar character and hence reduced reactivity of the -glucosyl azide.
Traceless Staudinger ligation of glycosyl azides with triaryl phosphines: Stereoselective synthesis of glycosyl amides
Bianchi, Aldo,Bernardi, Anna
, p. 4565 - 4577 (2007/10/03)
α-Glycosyl amides can be synthesized from the corresponding O-benzyl-α-glycosyl azides using a traceless Staudinger ligation with diphenylphosphanyl-phenyl esters 4. All the phosphines employed and their phenol precursors are stable to air at 4 °C for months. Fast intramolecular trapping of the reduction intermediates results in the direct formation of the amide link, which, in turn, prevents epimerisation and allows retention of configuration at the anomeric carbon. Yields and α-selectivity are high when the reaction is performed in polar aprotic solvents. Removal of the benzyl ether protecting groups is achieved by catalytic hydrogenation. α-Glycosyl amides represent a class of virtually unexplored nonhydrolyzable monosaccharide derivatives that may find a useful application as sugar mimics. Conformational studies by NMR spectroscopy confirm that deprotected α-glycosyl amides in the gluco, galacto, and fuco series retain the normal pyranose conformation of the monosaccharide. The reaction of phosphines 4 with tetra-O-acetyl-glycosyl azides is nonstereoconservative, and β-glycosyl amides are obtained in good yields and with complete stereoselectivity starting from both α and β azides.
Azide and Cyanide Displacements via Hypervalent Silicate Intermediates
Soli, Eric D.,Manoso, Amy S.,Patterson, Michael C.,DeShong, Philip,Favor, David A.,Hirschmann, Ralph,Smith III, Amos B.
, p. 3171 - 3177 (2007/10/03)
Hypervalent azido- and cyanosilicate derivatives, prepared in situ by the reaction of trimethylsilyl azide or trimethylsilyl cyanide, respectively, with tetrabutylammonium fluoride, are effective sources of nucleophilic azide or cyanide. Primary and secondary alkyl halides and sulfonates undergo rapid and efficient azide or cyanide displacement in the absence of phase transfer catalysts with the silicate derivatives. Application of these reagents to the stereoselective synthesis of glycosyl azide derivatives is reported.
Neighbouring group participation of C-6 substituents of glucose derivatives on the stereoselectivity of the N-glycosidic linkage of glycopeptides
Zhang, Hong,Wang, Yali,Thuermer, Rene,Parvez, Khalid,Choudhary, Iqbal,Atta-Ur-Rahman,Voelter, Wolfgang
, p. 692 - 698 (2007/10/03)
The first example of a glycopeptide with a direct N-α-glycosidic linkage between the trisaccharide and the amino acid residue was found in the glomerular basement membrane of rats. In connection with the total synthesis of nephritogenoside, glycosyl azides with different protecting groups and carbohydrate chain lengths are synthesized, reduced to the corresponding glycosyl amines and coupled with Z-Asp-OBzl. Remarkable differences in the α:β ratio of the condensation products are observed, caused by neighbouring group participation.
