7473-45-2Relevant academic research and scientific papers
Highly stereoselective glycosidation of ribose solubilized in apolar organic media via host-guest complexation
Tanaka, Yasutaka,Khare, Chinmai,Yonezawa, Masaki,Aoyama, Yasuhiro
, p. 6193 - 6196 (1990)
Ribose complexed with resorcinol-dodecanal cyclotetramer via hydrogen bonding in CCl4 undergoes highly stereoselective glycosidation with methanol to give methyl β-ribofuranoside under mild and neutral conditions.
Furanosic forms of sugars: Conformational equilibrium of methyl β-d-ribofuranoside
écija, Patricia,Uriarte, Iciar,Spada, Lorenzo,Davis, Benjamin G.,Caminati, Walther,Basterretxea, Francisco J.,Lesarri, Alberto,Cocinero, Emilio J.
, p. 6241 - 6244 (2016)
The investigation of an isolated ribofuranose unit in the gas phase reveals the intrinsic conformational landscape of the biologically active sugar form. We report the rotational spectra of two conformers of methyl β-d-ribofuranoside in a supersonic jet expansion. Both conformers adopt a near twisted (3T2) ring conformation with the methoxy and hydroxymethyl substituents involved in various intramolecular hydrogen bonds.
Stereoselective Synthesis of Ribofuranoid exo-Glycals by One-Pot Julia Olefination Using Ribofuranosyl Sulfones
Oka, Natsuhisa,Mori, Ayumi,Suzuki, Kanna,Ando, Kaori
, p. 657 - 673 (2020/12/23)
One-pot Julia olefination using ribofuranosyl sulfones is described. The α-anomers of the ribofuranosyl sulfones were synthesized with complete α-selectivity via the glycosylation of heteroarylthiols using ribofuranosyl iodides as glycosyl donors and the subsequent oxidation of the resulting heteroaryl 1-thioribofuranosides with magnesium monoperphthalate (MMPP). The Julia olefination of the α-ribofuranosyl sulfones with aldehydes proceeded smoothly in one pot to afford the thermodynamically less stable (E)-exo-glycals with modest-to-excellent stereoselectivity (up to E/Z = 94:6) under the optimized conditions. The E selectivity was especially high for aromatic aldehydes. In contrast, the (Z)-exo-glycal was obtained as the main product with low stereoselectivity when the corresponding β-ribofuranosyl sulfone was used (E/Z = 41:59). The remarkable impact of the anomeric configuration of the ribofuranosyl sulfones on the stereoselectivity of the Julia olefination has been rationalized using density functional theory (DFT) calculations. The protected ribose moiety of the resulting exo-glycals induced completely α-selective cyclopropanation on the exocyclic carbon-carbon double bond via the Simmons-Smith-Furukawa reaction. The 2-cyanoethyl group was found to be useful for the protection of the exo-glycals, as it could be removed without affecting the exocyclic C=C bond.
MODIFIED OLIGOMERIC COMPOUNDS AND USES THEREOF
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Page/Page column 119-121, (2021/02/19)
The present disclosure provides oligomeric compounds comprising a modified oligonucleotide having at least one stereo-non-standard nucleoside. An oligomeric compound comprising a modified oligonucleotide consisting of 12-30 linked nucleosides, wherein at least one nucleoside of the modified oligonucleotide is a stereo-non-standard nucleoside; and wherein the oligomeric compound is selected from among an RNAi compound, a modified CRISPR compound, and an artificial mRNA compound.
Novel saccharide bio-based cyclic phosphorus/phosphonate as well as preparation method and application thereof
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Paragraph 0039; 0041-0042, (2021/09/04)
The invention discloses novel saccharide bio-based cyclic phosphorus/phosphonate as well as a preparation method and application thereof, and belongs to the field of compounds. The cyclic phosphorus/phosphonate is prepared by the following steps: reacting D-xylose with acetyl chloride to obtain an intermediate product, and then reacting with dichlorophosphate or phosphonic dichloride under the action of an acid-binding agent to obtain a target product. The preparation method is high in yield, simple in process, low in raw material cost and small in environmental pollution, and the prepared cyclic phosphorus/phosphonate flame retardant is outstanding in flame retardance and easy to industrialize.
BIOMARKER PANEL TARGETED TO DISEASES DUE TO MULTIFACTORIAL ONTOLOGY OF GLYCOCALYX DISRUPTION
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Paragraph 0292; 0306, (2021/04/02)
The present disclosure provides biomarkers useful as companion diagnostics for detecting glycocalyx-based disease that is amenable to treatment using compounds designed for improving the condition of the glycocalyx and/or reducing inflammation and/or oxidative damage, as well as related compositions, kits, and methods.
Synthesis of 1,2,3-triazolyl nucleoside analogues and their antiviral activity
Andreeva, Olga V.,Garifullin, Bulat F.,Zarubaev, Vladimir V.,Slita, Alexander V.,Yesaulkova, Iana L.,Saifina, Liliya F.,Shulaeva, Marina M.,Belenok, Maya G.,Semenov, Vyacheslav E.,Kataev, Vladimir E.
, p. 473 - 490 (2020/09/22)
Abstract: Based on the fact that a search for influenza antivirals among nucleoside analogues has drawn very little attention of chemists, the present study reports the synthesis of a series of 1,2,3-triazolyl nucleoside analogues in which a pyrimidine fragment is attached to the ribofuranosyl-1,2,3-triazol-4-yl moiety by a polymethylene linker of variable length. Target compounds were prepared by the Cu alkyne-azide cycloaddition (CuAAC) reaction. Derivatives of uracil, 6-methyluracil, 3,6-dimethyluracil, thymine and quinazolin-2,4-dione with ω-alkyne substituent at the N1 (or N5) atom and azido 2,3,5-tri-O-acetyl-D-β-ribofuranoside were used as components of the CuAAC reaction. All compounds synthesized were evaluated for antiviral activity against influenza virus A/PR/8/34/(H1N1) and coxsackievirus B3. The best values of IC50 (inhibiting concentration) and SI (selectivity index) were demonstrated by the lead compound 4i in which the 1,2,3-triazolylribofuranosyl fragment is attached to the N1 atom of the quinazoline-2,4-dione moiety via a butylene linker (IC50 = 30?μM, SI = 24) and compound 8n in which the 1,2,3-triazolylribofuranosyl fragment is attached directly to the N5 atom of the 6-methyluracil moiety (IC50 = 15?μM, SI = 5). According to theoretical calculations, the antiviral activity of the 1,2,3-triazolyl nucleoside analogues 4i and 8n against H1N1 (A/PR/8/34) influenza virus can be explained by their influence on the functioning of the polymerase acidic protein (PA) of RNA-dependent RNA polymerase (RdRP). Graphic abstract: [Figure not available: see fulltext.]
ANTIVIRAL NUCLEOSIDES AND DERIVATIVES THEREOF
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Page/Page column 44, (2020/08/22)
Disclosed herein are nucleoside compounds and derivatives thereof, pharmaceutical compositions containing same, and their methods of synthesis. The compounds are useful in treating orthomyxovirus infections, such as influenza infections.
Synthesis of remdesivir key intermediate 2, 3, 5-tribenzyloxy-D-ribotide-1, 4-lactone
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Paragraph 0018-0021, (2020/07/21)
The invention relates to synthesis of a remdesivir key intermediate 2, 3, 5-tribenzyloxy-D-ribotide-1, 4-lactone. The invention discloses a synthesis method of 2, 3, 5-tribenzyloxy-D-ribotide-1, 4-lactone, and belongs to the field of organic synthesis. The method includes: taking D-ribose as an initial raw material, in methanol, using concentrated sulfuric acid as a catalyst, synthesizing a methoxy compound 2, then fully stirring the substances in a saturated sodium hydroxide solution, adding tetrahydrofuran and n-butylammonium hydrogen sulfate, and then adding benzyl bromide to synthesize a compound 3, dissolving the compound 3 in tetrahydrofuran and then performing catalysis with concentrated sulfuric acid, and performing reflux stirring overnight treatment to obtain a compound 4, dissolving the compound 4 into dichloromethane and water, adding sodium bicarbonate and TEMPO, slowly adding sodium hypochlorite at 0DEG C, raising the temperature to room temperature, and conducting stirring overnight treatment to obtain a compound 5. The method has the characteristics of easily available raw materials and low production cost, each process step is simple and easy to treat, the yield ofthe whole route reaches 43% or above, industrial production is easy to realize, and a basis is provided for industrialization of remdesivir and subsequent derivatives thereof.
Manno- epi-cyclophellitols Enable Activity-Based Protein Profiling of Human α-Mannosidases and Discovery of New Golgi Mannosidase II Inhibitors
Aerts, Johannes M. F. G.,Armstrong, Zachary,Beenakker, Thomas J. M.,Boot, Rolf G.,Codée, Jeroen D. C.,Davies, Gideon J.,De Boer, Casper,Debets, Marjoke F.,Florea, Bogdan I.,Geurink, Paul P.,Hissink, Colin,Johnson, Rachel,Kuo, Chi-Lin,Lahav, Dani?l,Liu, Bing,Ovaa, Huib,Overkleeft, Herman S.,Van Der Marel, Gijsbert M.,Van Der Stelt, Mario,Van Rijssel, Erwin R.,Wong, Chung-Sing,Wu, Liang
supporting information, p. 13021 - 13029 (2020/09/01)
Golgi mannosidase II (GMII) catalyzes the sequential hydrolysis of two mannosyl residues from GlcNAcMan5GlcNAc2 to produce GlcNAcMan3GlcNAc2, the precursor for all complex N-glycans, including the branched N-glycans associated with cancer. Inhibitors of GMII are potential cancer therapeutics, but their usefulness is limited by off-target effects, which produce α-mannosidosis-like symptoms. Despite many structural and mechanistic studies of GMII, we still lack a potent and selective inhibitor of this enzyme. Here, we synthesized manno-epi-cyclophellitol epoxide and aziridines and demonstrate their covalent modification and time-dependent inhibition of GMII. Application of fluorescent manno-epi-cyclophellitol aziridine derivatives enabled activity-based protein profiling of α-mannosidases from both human cell lysate and mouse tissue extracts. Synthesized probes also facilitated a fluorescence polarization-based screen for dGMII inhibitors. We identified seven previously unknown inhibitors of GMII from a library of over 350 iminosugars and investigated their binding modalities through X-ray crystallography. Our results reveal previously unobserved inhibitor binding modes and promising scaffolds for the generation of selective GMII inhibitors.
