- Isoniazid Conjugates with D-Arabinofuranose
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Glycoconjugates with isoniazid attached to the hydroxy group at the С5 atom of D-arabinofuranose via the spacers differing in length have been synthesized.
- Andreeva,Kataev
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p. 1411 - 1417
(2018/09/10)
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- Synthesis of Nucleosides through Direct Glycosylation of Nucleobases with 5-O-Monoprotected or 5-Modified Ribose: Improved Protocol, Scope, and Mechanism
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Simplifying access to synthetic nucleosides is of interest due to their widespread use as biochemical or anticancer and antiviral agents. Herein, a direct stereoselective method to access an expansive range of both natural and synthetic nucleosides up to a gram scale, through direct glycosylation of nucleobases with 5-O-tritylribose and other C5-modified ribose derivatives, is discussed in detail. The reaction proceeds through nucleophilic epoxide ring opening of an in situ formed 1,2-anhydrosugar (termed “anhydrose”) under modified Mitsunobu reaction conditions. The scope of the reaction in the synthesis of diverse nucleosides and other 1-substituted riboside derivatives is described. In addition, a mechanistic insight into the formation of this key glycosyl donor intermediate is provided.
- Downey, A. Michael,Pohl, Radek,Roithová, Jana,Hocek, Michal
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supporting information
p. 3910 - 3917
(2017/03/27)
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- Total synthesis of pachastrissamine together with its 4-epi-congener via [3,3]-sigmatropic rearrangements and antiproliferative/cytotoxic evaluation Dedicated to Associated Professor Ladislav Knie?o on the occasion of his 70th birthday
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Synthesis of the HCl salts of two anhydrophytosphingosines, jaspine B (1) and its 4-epi-congener 5 from easily available dimethyl l-tartrate and/or l-arabinose, is described. The key transformations are the efficient incorporation of a chiral amino group
- Martinková, Miroslava,Mezeiová, Eva,Fabi?íková, Milica,Gonda, Jozef,Pilátová, Martina,Moj?i?, Ján
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- Yarrowia lipolytica dehydrogenase/reductase: An enzyme tolerant for lipophilic compounds and carbohydrate substrates
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Yarrowia lipolytica short chain dehydrogenase/reductase (YlSDR) was expressed in Escherichia coli, purified and characterized in vitro. The substrate scope for YlSDR mediated oxidation was investigated with alcohols and unprotected carbohydrates spectrophotometrically, revealing a preference for secondary compared to primary alcohols. In reduction direction, YlSDR was highly active on ribulose and fructose, suggesting that the enzyme is a mannitol-2-dehydrogenase. In order to explore substrate tolerance especially for space-demanding, lipophilic protecting groups, 5-O-trityl-d-ribitol and 5-O-trityl-α,β-d-ribose were investigated as substrates: YlSDR oxidized 5-O-trityl-d-ribitol and 5-O-trityl-α,β-d-ribose and reduced the latter at the expense of NADP(H).
- Napora, Kamila,Wrodnigg, Tanja M.,Kosmus, Patrick,Thonhofer, Martin,Robins, Karen,Winkler, Margit
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p. 3393 - 3395
(2013/06/27)
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- Simple approach to 1-O-protected (R)- and (S)-glycerols from l- and d-arabinose for glycerol nucleic acids (GNA) monomers research
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5-O-Protected (-Tr, -Sitert-BuPh2) d- and l-arabinofuranoses easily available in multigram quantities were converted to (S)- and (R)-1-O-protected glycerols, respectively, via oxidation (NaIO4) and reduction (NaBH4). Sourc
- Doboszewski, Bogdan,Herdewijn, Piet
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scheme or table
p. 3853 - 3855
(2011/08/06)
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- A simple synthesis of C-8 modified 2-keto-3-deoxy-d-manno-octulosonic acid (KDO) derivatives
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This paper describes a simple and efficient method with which to prepare C-8 modified 2-keto-3-deoxy-D-manno-octu-losonic acid (KDO) derivatives from C-5 modified arabinose derivatives. Georg Thieme Verlag Stuttgart.
- Winzar, Renee,Philips, Jessica,Kiefel, Milton J.
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scheme or table
p. 583 - 586
(2010/10/02)
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- Synthesis of putative chain terminators of mycobacterial arabinan biosynthesis
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The synthesis of a variety of arabinose derivatives that have been modified at C-5 was achieved from d-arabinose. The 5-fluoro and 5-methoxy compounds were converted into the corresponding farnesyl phosphodiesters as putative chain terminators of mycobact
- Smellie, Iain A.,Bhakta, Sanjib,Sim, Edith,Fairbanks, Antony J.
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p. 2257 - 2266
(2008/03/14)
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- An efficient synthesis of a dimer of the tetrasaccharide present in motif B of the Mycobacterium tuberculosis cell wall
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An efficient method for the synthesis of 3,5-branched octaarabinoside, which is a dimer of the tetrasaccharide present in motif B of the Mycobacterium tuberculosis cell wall, has been developed by using 2,3,5-tri-O-benzoyl-α- D-arabinofuranosyl trichloroa
- Mei, Xiangdong,Ning, Jun
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p. 2267 - 2272
(2007/10/03)
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- Synthesis of optically active olivil type of lignan from L-arabinose using threo-selective aldol condensation as a key reaction.
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The threo-selective aldol condensation of (3R, 4S)-3-hydroxy-5-trityloxy-4-pentanolide, which was prepared from L-arabinose, with piperonal was applied to the stereoselective synthesis of the olivil type of lignan, (2R, 3R, 4R)-4-benzyl-4-hydroxy-3-hydroxymethyl-2-(3,4-methylenedioxyphenyl)tetrahydrofuran.
- Yamauchi,Kinoshita
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p. 2320 - 2327
(2007/10/03)
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- Stereoselective model synthesis of the optically active olivil type of lignan from D-xylose.
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The olivil type of lignan, (2S,3R,4R)-4-benzyl-4-hydroxy - 3 - hydroxymethyl - 2 - (3,4 - methylenedioxyphenyl)tetrahydrofuran, was stereoselectively synthesized from D-xylose.
- Yamauchi,Kinoshita
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p. 1563 - 1571
(2007/10/03)
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- A facile synthesis of 5-thio-L-fucose and 5-thio-D-arabinose from D-arabinose
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5-Thio-L-fucopyranose tetraacetate was synthesized in 11 steps from 5-O-trityl-D-arabinofuranose or D-arabinose diethyl dithioacetal by one-carbon elongation at C-5. Highly diastereoselective addition of MeLi in ether to a 1,2-O-isopropylidene-β-D-arabino
- Izumi, Masayuki,Tsuruta, Osamu,Hashimoto, Hironobu
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p. 287 - 302
(2007/10/03)
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- A Novel Synthesis of Sulfamoyl Nucleosides
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The sulfamoylated ribose derivative 8 was prepared on a kilogram scale, and used in conjunction with various heterocycles to prepare a series of natural and unnatural 5-O-sulfamoyl nucleosides (10 - 32).A modification of the Vorbrueggen-Hilbert-Johnson reaction conditions for nucleoside formation was used.
- Kristinsson, Haukur,Nebel, Kurt,O'Sullivan, Anthony C.,Struber, Fritz,Winkler, Tammo,Yamaguchi, Yasuchika
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p. 6825 - 6838
(2007/10/02)
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