13089-27-5Relevant academic research and scientific papers
NOVEL IMMUNODULATING SMALL MOLECULES
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Paragraph 0187; 0192, (2020/01/31)
The present invention includes novel compositions and methods for treating comprising a compound with the Formula I: where n = 0-5; X = NH, O, S, CH2; Y = Phenyl, a phenyl group substituted with at least one methyl, a phenyl group substituted with at least one nitro, a phenyl group substituted with at least one nitrogen, a phenyl group substituted with at least one boron, aryl, substituted aryl, heteroaryl, four to six membered cycloalkyl, four to six membered heterocycloalkyl; R = H, C(O)R2, SO2R2; R1 = H, C(O)R2, SO2R2; R2 = Ethyl, methyl, isopropyl, n-propyl, t-butyl, n- butyl, NH2, NR3R4; R3, R4 = Ethyl, methyl, isopropyl, n-propyl, t-butyl, n-butyl, three to six membered cycloalkyl and Z = NH, O, S, CH2 or none, wherein the amount of the compound is selected to either inhibit or activate the immune response.
Glycosynthase with broad substrate specificity-an efficient biocatalyst for the construction of oligosaccharide library
Wei, Jinhua,Lv, Xun,Lue, Yang,Yang, Gangzhu,Fu, Lifeng,Yang, Liu,Wang, Jianjun,Gao, Jianhui,Cheng, Shuihong,Duan, Qian,Jin, Cheng,Li, Xuebing
supporting information, p. 2414 - 2419 (2013/05/23)
A versatile glycosynthase (TnG-E338A) with strikingly broad substrate scope has been developed from Thermus nonproteolyticus β-glycosidase (TnG) by using site-directed mutagenesis. The practical utility of this biocatalyst has been demonstrated by the facile generation of a small library containing various oligosaccharides and a steroidal glycoside (total 25 compounds) in up to 100 % isolated yield. Moreover, an array of eight gluco-oligosaccharides has been readily synthesized by the enzyme in a one-pot, parallel reaction, which highlights its potential in the combinatorial construction of a carbohydrate library that will assist glycomic and glycotherapeutic research. Significantly, the enzyme provides a means by which glycosynthase technology may be extended to combinatorial chemistry.
Glycosylated tris-bipyridine ferrous complexes to provide dynamic combinatorial libraries for probing carbohydrate-carbohydrate interactions
Nakamura, Motomi,Tsutsumi, Mayuka,Ishikawa, Yoshiaki,Umemiya, Haruka,Izawa, Kazumi,Abe, Haruka,Togashi, Yosuke,Kinone, Tatsuya,Sekiguchi, Sho,Igumi, Mihiro,Ide, Kanako,Hasegawa, Teruaki,Hasegawa, Toki
supporting information, p. 3019 - 3026 (2013/03/29)
2,2-Bipyridines having β-lactoside, β-d-glucoside, β-d-galactoside, and N-acetyl-β-d-glucosaminide were prepared and then, complexed with ferrous ion to afford trivalent glycoclusters having tris-bipyridine ferrous complex cores. Each glycocluster provides a dynamic combinatorial library composed of four diastereomeric stereoisomers (Δmer, Δfac, Λmer, and Λfac) whose ratios depend on their relative stabilities. CD spectral analyses of these glycoclusters showed that various cations (Na+, Mg2+, K+ or Ca2+) enriched Δ-forms of the glycocluster having β-lactosides and N-acetyl-β-d-glucosaminides possibly by cations-induced intramolecular carbohydrate-carbohydrate interactions.
Syntheses of the 3- and 4-thio analogues of 4-nitrophenyl 2-acetamido-2-deoxy-β-d-gluco- and galactopyranoside
Chen, Hong-Ming,Withers, Stephen G.
, p. 2212 - 2222 (2008/02/12)
The syntheses of 4-nitrophenyl β-glycosides of the 3-thio and 4-thio analogues of the two principal 2-acetamido-2-deoxy-hexoses found in living systems, GlcNAc and GalNAc, are described. While synthesis of the 4-thio analogues could be achieved via nucleophilic displacements of sulfonate derivatives with thioacetate, problems with neighbouring group acetamido participation necessitated the use of sulfamidate intermediates for the 3-thio analogues. These 3- and 4-thio analogues are employed in the chemo-enzymatic synthesis of thio-oligosaccharide analogues of structures present in glycosaminoglycans, glycoproteins and glycolipids.
Cyanodeoxy-glycosyl derivatives as substrates for enzymatic reactions
Carmona, Ana T.,Fialova, Pavla,Kren, Vladimir,Ettrich, Rudiger,Martinkova, Ludmila,Moreno-Vargas, Antonio J.,Gonzalez, Cristina,Robina, Inmaculada
, p. 1876 - 1885 (2007/10/03)
Synthetic routes for the preparation of new sugar nitriles 8-10 derived from 2-acetamido-2-deoxy-β-D-glucopyranosides bearing a cyano group at the C-5 or C-6 position are presented. In an attempt to prepare the glycosyl azide 10 by treatment of tosylate 23 with KCN/DMF at 60°C, an intramolecular 1,3-dipolar cycloaddition reaction occurred to give the highly constrained nonisolable tetrazole 24, which was readily converted into the imino-azido compound 25 through an azido-tetrazole tautomerism. Compounds 8 and 10 were found to be poorer substrates of fungal β-N-acetylhexosaminidases than compound 9 and none of these compounds was accepted as substrates of the nitrilase or nitrile hydratase. Docking of the nitriles 8-10 in the active site of the β-N-acetylhexosaminidase from Aspergillus oryzae gave interaction energies comparable with the natural substrate. Based on these data, which indicate strong binding of these compounds (8 > 9 > 10) to the active site, it has been proposed that some cyano derivatives may act as competitive inhibitors of β-N-acetylhexosaminidases. This hypothesis is consistent with enzyme inhibition experiments which showed strong inhibitory properties of compound 9 (KI = 0.37 mM) and in particular of compound 8 (KI = 7.6 μM). Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
A phase-transfer glucosamination of phenols catalyzed by polyethylene glycol
Kur'yanov,Priskoka,Chupakhina,Chirva
, p. 300 - 301 (2008/02/02)
Glycosylation of phenols with α-D-glucosaminyl chloride peracetate catalyzed by polyethylene glycol (PEG) was carried out in a solid-liquid phase transfer system at room temperature. The results were compared with those previously obtained for the catalys
Aromatic crown ethers as phase transfer catalysts in the synthesis of N-acetylglucosamine β-aryl glycosides
Chupakhina,Kur'yanov,Chirva,Grigorash,Kotlyar,Kamalov
, p. 301 - 303 (2007/10/03)
The crown ether-catalyzed glycosylation of phenol, 4-methoxyphenol, and 4-nitrophenol was studied under phase transfer conditions in solid-liquid system. The asymmetric dibenzocrown esters are superior to [3.3]dibenzo-18- crown-6 and 15-crown-5 in the cat
Synthesis of N-Acetylglucosamine Aryl β-Glycosides Catalyzed by Crown Compounds
Kur'yanov,Chupakhina,Zemlyakov,Kotlyar,Kamalov,Chirva
, p. 385 - 389 (2007/10/03)
Glycosylation of various phenols with α-D-glucosaminyl chloride peracetate in a solid phase-liquid system catalyzed by crown compounds was studied. The highest yields of aryl β-glycosides were observed at room temperature in acetonitrile using anhydrous p
A facile access to aryl α-sialosides: The combination of a volatile amine base and acetonitrile in glycosidation of sialosyl chlorides
Kuboki, Atsuhito,Sekiguchi, Takahiro,Sugai, Takeshi,Ohta, Hiromichi
, p. 479 - 482 (2007/10/03)
We have succeeded in achieving a facile access to 4-nitrophenyl and 4-methylumbelliferyl-α-sialosides. To sialosyl chlorides which are fully protected with acetyl groups as glycosyl donors, the action of phenols with diisopropylethylamine in acetonitrile brought about high yield as well as facile product isolation.
Glycosidase-catalysed oligosaccharide synthesis: preparation of N-acetylchitooligosaccharides using the β-N-acetylhexosaminidase of Aspergillus oryzae
Singh, Suddham,Packwood, John,Samuel, Christopher J.,Critchley, P.,Crout, David H. G.
, p. 293 - 306 (2007/10/03)
The β-N-acetylhexosaminidase of Aspergillus oryzae catalyses the formation of 2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-deoxy-D-glucopyranose (di-N-acetylchitobiose) and 2-acetamido-6-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-deoxy-D-glucopyranose from p-nitrophenyl 2-acetamido-2-deoxy-β-D-glucopyranoside and 2-acetamido-2-deoxy-D-glucopyranose.The ratio of the two disaccharides is time-dependent.The ratio of (14)- to (16)-isomers is a maximum (ca. 9:1) at the point of disappearance of the glycosyl donor.If left to evolve, the ratio changes to 92:8 in favour of the (16)-isomer.Either the (14)- or the (16)-isomer can be isolated by treating the appropriately enriched disaccharide mixture with the β-N-acetylhexosaminidase of Jack bean (Canavalia ensiformis) or the β-N-acetylhexosaminidase of A. oryzae, respectively.Di-N-acetylchitobiose is an efficient donor of 2-acetamido-2-deoxy-D-glucopyranosyl units in reactions catalysed by the N-acetylhexosaminidase of A. oryzae.Di-N-acetylchitobiose itself acts as acceptor to give tri-N-acetylchitotriose .As the trisaccharide accumulates it, in turn, acts as acceptor giving tetra-N-acetylchitotetraose .The product mixture consisting of mono-, di-, tri-, and tetra-saccharides is conveniently separated by charcoal-Celite chromatography. Keywords: Glycosidase; N-acetylhexosaminidase; Chitooligosaccharides; Enzymatic synthesis.
