55726-00-6Relevant articles and documents
Isoniazid Conjugates with D-Arabinofuranose
Andreeva,Kataev
, p. 1411 - 1417 (2018/09/10)
Glycoconjugates with isoniazid attached to the hydroxy group at the С5 atom of D-arabinofuranose via the spacers differing in length have been synthesized.
Synthesis of Nucleosides through Direct Glycosylation of Nucleobases with 5-O-Monoprotected or 5-Modified Ribose: Improved Protocol, Scope, and Mechanism
Downey, A. Michael,Pohl, Radek,Roithová, Jana,Hocek, Michal
supporting information, p. 3910 - 3917 (2017/03/27)
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.
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
Martinková, Miroslava,Mezeiová, Eva,Fabi?íková, Milica,Gonda, Jozef,Pilátová, Martina,Moj?i?, Ján
, p. 6 - 24 (2015/02/05)
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
Yarrowia lipolytica dehydrogenase/reductase: An enzyme tolerant for lipophilic compounds and carbohydrate substrates
Napora, Kamila,Wrodnigg, Tanja M.,Kosmus, Patrick,Thonhofer, Martin,Robins, Karen,Winkler, Margit
, p. 3393 - 3395 (2013/06/27)
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).
Simple approach to 1-O-protected (R)- and (S)-glycerols from l- and d-arabinose for glycerol nucleic acids (GNA) monomers research
Doboszewski, Bogdan,Herdewijn, Piet
scheme or table, p. 3853 - 3855 (2011/08/06)
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
A simple synthesis of C-8 modified 2-keto-3-deoxy-d-manno-octulosonic acid (KDO) derivatives
Winzar, Renee,Philips, Jessica,Kiefel, Milton J.
scheme or table, p. 583 - 586 (2010/10/02)
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.
Synthesis of putative chain terminators of mycobacterial arabinan biosynthesis
Smellie, Iain A.,Bhakta, Sanjib,Sim, Edith,Fairbanks, Antony J.
, p. 2257 - 2266 (2008/03/14)
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
An efficient synthesis of a dimer of the tetrasaccharide present in motif B of the Mycobacterium tuberculosis cell wall
Mei, Xiangdong,Ning, Jun
, p. 2267 - 2272 (2007/10/03)
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
Synthesis of optically active olivil type of lignan from L-arabinose using threo-selective aldol condensation as a key reaction.
Yamauchi,Kinoshita
, p. 2320 - 2327 (2007/10/03)
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.
Stereoselective model synthesis of the optically active olivil type of lignan from D-xylose.
Yamauchi,Kinoshita
, p. 1563 - 1571 (2007/10/03)
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.
