- Xylonucleic acid: Synthesis, structure, and orthogonal pairing properties
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There is a common interest for studying xeno-nucleic acid systems in the fields of synthetic biology and the origin of life, in particular, those with an engineered backbone and possessing novel properties. Along this line, we have investigated xylonuclei
- Maiti, Mohitosh,Maiti, Munmun,Knies, Christine,Dumbre, Shrinivas,Lescrinier, Eveline,Rosemeyer, Helmut,Ceulemans, Arnout,Herdewijn, Piet
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- PROCESSES FOR PREPARING 2-DIHALO RIBOLACTONES
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Methods for forming 2-bromo, 2-fluoro ribofuranose intermediates and 2-chloro, 2- fluoro ribofuranose intermediates for use in preparing antiviral nucleosides are disclosed. Methods for forming nucleosides, and nucleoside prodrugs, using the intermediates, are also disclosed. The methods all produce intermediates, and the resulting nucleosides and prodrugs thereof, wherein the chirality of the carbon at the 2-position is controlled. In some embodiments, the chemistry involves using chiral auxiliaries, such as (R)-2,2-dimethyl-l,3- dioxolane-4-carbaldehyde, and in other embodiments, the chemistry involves using chiral starting materials, such as D-xylose.
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Page/Page column 73; 74
(2017/06/21)
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- Methanesulfonic-acid-catalysed ring opening and glycosylation of 1,2-(Acetylcyclopropane)-annulated d -lyxofuranose
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A mild and effective method for the synthesis of 2-C-branched disaccharides, glycoconjugates, and nucleoside analogues is described. 1,2-(acetylcyclopropane)-annulated D-lyxofuranose underwent ring opening catalysed by CH3SO3H to act as an efficient glycosyl donor and give the glycosylation products in good yields and with high diastereoselectivities. Copyright
- Wang, Cong,Ma, Xiaofeng,Zhang, Jichao,Tang, Qin,Jiao, Wei,Shao, Huawu
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p. 4592 - 4599
(2014/08/05)
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- Synthesis of purine nucleosides from D -glucuronic acid derivatives and evaluation of their cholinesterase-inhibitory activities
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Glucuronolactones were used as precursors for N9 and N 7 purine nucleosides containing glucuronic acid derivatives in their structures. Acetylated N-benzylglucofuran- and glucopyranuronamides were synthesized in a few steps from glucofuranurono-6,3-lactone. They were converted into the corresponding furanosyl and pyranosyl uronamide-based nucleosides by N-glycosylation with silylated 2-acetamido-6-chloropurine in the presence of trimethylsilyl triflate. The triacetylated bicyclic lactone was coupled itself with the nucleobase to give bicyclic N9,N7 nucleosides. Tri-O-acetylglucopyranurono-6,1-lactone was used for the first time as a glycosyl donor for N-glycosylation, and led to β-configured N9- and N7-linked purinylglucuronides under reaction conditions similar to those used with the 1-O-acetyl-substituted glycosyl donors. The cholinesterase inhibitory profiles of the synthetic nucleosides bearing glucuronic acid derivatives as glycons were evaluated, and they showed moderate selective acetylcholinesterase inhibitory activities (Ki = 14.78-50.53 μM). The best inhibition was shown by the furanosyl N 9-linked uronamide-based purine nucleoside. The synthesis of furanosyl and pyranosyl N9 and N7 purine nucleosides containing glucofuranurono-6,3-lactone, N-benzylglucuronamide, and glucuronic acid moieties is reported. Glucuronolactones were used as glycosyl donors or converted into suitable 1-O-acetyl derivatives for purine glycosylation. Some nucleosides showed moderate and selective inhibition of acetylcholinesterase. Copyright
- Xavier, Nuno M.,Schwarz, Stefan,Vaz, Pedro D.,Csuk, Rene,Rauter, Amelia P.
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p. 2770 - 2779
(2014/05/06)
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- InCl3 catalyzed highly diastereoselective [3 + 2] cycloaddition of 1,2-cyclopropanated sugars with aldehydes: A straightforward synthesis of persubstituted bis -tetrahydrofurans and perhydrofuro[2,3- b ]pyrans
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A mild and efficient strategy for the construction of persubstituted bis-tetrahydrofuran and perhydrofuro[2,3-b]pyran derivatives has been developed. Persubstituted cyclization products were obtained in good to excellent yields. The [3 + 2] cycloaddition of 1,2-cyclopropanated sugars with aldehydes in the presence of InCl3 is highly diastereoselective.
- Ma, Xiaofeng,Tang, Qin,Ke, Jun,Yang, Xinglong,Zhang, Jichao,Shao, Huawu
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p. 5170 - 5173
(2013/11/06)
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- Straightforward and highly diastereoselective synthesis of 2,2-di-substituted perhydrofuro[2,3-b]pyran (and furan) derivatives promoted by BiCl3
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An effective and facile method for the synthesis of 2,2-di-substituted perhydrofuro[2,3-b]pyran (and furan) derivatives is described. The cyclization of 1,2-cyclopropanated sugars with olefins in the presence of BiCl3 is highly diastereoselecti
- Ma, Xiaofeng,Tang, Qin,Ke, Jun,Zhang, Jichao,Wang, Cong,Wang, Haibo,Li, Yuxue,Shao, Huawu
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supporting information
p. 7085 - 7087
(2013/09/02)
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- Design and synthesis of carbohydrate based medium sized sulfur containing benzannulated macrocycles: Applications of Sonogashira and Heck coupling
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Palladium catalyzed intramolecular Sonogashira and Heck coupling reactions have been applied for diversity-oriented synthesis of sulfur containing carbohydrate based medium sized ring macrocycles. The process involves design and synthesis of building bloc
- Hussain, Altaf,Yousuf, Syed Khalid,Sharma, Deepak K.,Mallikharjuna Rao,Singh, Baldev,Mukherjee, Debaraj
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supporting information
p. 5517 - 5524
(2013/07/05)
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- C1-symmetric diphosphite ligands derived from carbohydrates: Influence of structural modifications on the rhodium-catalyzed asymmetric hydroformylation of styrene
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New 3,5-diphosphite-substituted xylofuranoside (1b, 25a,b, and 26a,b) and glucofuranoside (3a, 7a, 8a,b) ligands with C1 symmetry have been prepared and used in the Rh-catalyzed asymmetric hydroformylation of styrene. The main structural features of these ligands are a) the presence of a 6-O-isopropyl group in ligands with a gluco configuration, b) the absence of 1,2-O-isopropylidene, a common group in many ligands with a furanoside skeleton, c) the presence of an alkyl chain bound to the 2-OH, and d) modification of the diol in the phosphite moiety. Modification of the carbohydrate backbone and diphosphite bridge affects the activity and selectivity of the reaction. Catalytic systems with ligands 1b and 8b were not active at 40 °C, although the formation of the expected hydride species [RhH(CO)2(1b)] was demonstrated by NMR spectroscopy. The highest enantioselectivity (83%) was obtained with the catalytic system Rh/8a. The complex [RhH(CO)2(8a)] was characterized by NMR spectroscopy using high-pressure techniques and was shown to exist in solution as two isomers in equilibrium; the two isomers adopt an equatorial-equatorial (eq-eq) configuration. Wiley-VCH Verlag GmbH & Co. KGaA, 2009.
- Gual, Aitor,Godard, Cyril,Claver, Carmen,Castillon, Sergio
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experimental part
p. 1191 - 1201
(2009/07/11)
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- Stereoselective 1,4-phenyl migration from silicon to carbon in α-siloxy cyclic acetal systems: A concise synthesis of 1,2-cis-phenyl C-glycoside and enantioenriched silanol
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The treatment of O-glycoside with alcohol in the presence of montmorillonite K10 clay and 4-? MS yields the 1,4-aryl migration product with a 1,2-cis-phenyl C-glycoside scaffold and a chiral silyl moiety with high stereoselectivity.
- Nakazaki, Atsuo,Usuki, Junji,Tomooka, Katsuhiko
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experimental part
p. 2064 - 2068
(2009/05/07)
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- Novel D-xylose derivatives stimulate muscle glucose uptake by activating AMP-activated protein kinase α
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Type 2 diabetes mellitus has reached epidemic proportions; therefore, the search for novel antihyperglycemic drugs is intense. We have discovered that D-xylose increases the rate of glucose transport in a non-insulin-dependent manner in rat and human myot
- Gruzman, Arie,Shamni, Ofer,Yakir, Moriya Ben,Sandovski, Daphna,Elgart, Anna,Alpert, Evgenia,Cohen, Guy,Hoffman, Amnon,Katzhendler, Yehoshua,Cerasi, Erol,Sasson, Shlomo
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body text
p. 8096 - 8108
(2009/12/07)
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- Oxetane δ-amino acids: Chemoenzymatic synthesis of 2,4-anhydro-5-N-(t-butoxycarbonyl)amino-D-lyxonic acid
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Starting from 1,2-O-isopropylidene-D-xylose, methyl 2,4-anhydro-3,5-di-O- benzyl-D-lyxonate (4) was synthesized. Debenzylation and transformation of the primary hydroxyl group yielded methyl 2,4-anhydro-5- N-(t-butoxycarbonyl)amino- D-lyxonate (9). While
- Dias Lucas, Susana,Iding, Hans,Alker, Andre,Peter Wessel, Hans,Pilar Rauter, Amelia
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p. 187 - 196
(2007/10/03)
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- Studies toward a synthesis of trilobatin B, a lignan from the liverwort Bazzania trilobata: Asymmetric construction of the tetrahydrofuran segment
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A novel and stereocontrolled process is described for the asymmetric synthesis of the tetrahydrofuran segment of a 2,3-dicarboxy-6,7-dihydroxy-1- (3′,4′-dihydroxyphenyl)-1,2- dihydronaphthalene mono-ester, trilobatin B, a lignan from the liverwort Bazzani
- Yoda, Hidemi,Nakaseko, Yuka,Takabe, Kunihiko
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p. 4217 - 4220
(2007/10/03)
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- Elucidation of the 2-C-methyl-D-erythritol 4-phosphate pathway for isoprenoid biosynthesis: Straightforward syntheses of enantiopure 1-deoxy-D-xylulose from pentose derivatives
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Optically pure 1-deoxy-D-xylulose, a key metabolite for feeding experiments in the methylerythritol phosphate pathway for isoprenoid biosynthesis, is conveniently synthesised from 1,2-O-isopropylidene-α-D-xylofuranose or from D-arabinose. This renders lab
- Hoeffler, Jean-Fran?ois,Grosdemange-Billiard, Catherine,Rohmer, Michel
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p. 3065 - 3067
(2007/10/03)
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- Template-directed intramolecular c-glycosidation. Cation- mediated synthesis of ketooxetanes from thioglycosides
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Bicyclic ketooxetanes may be assembled using cation-mediated cyclisation reactions of thioglycosides possessing silyl enol ether-containing side-chains.
- Craig, Donald,Munasinghe, V. Ranjit N.,Tierney, Jason P.,White, Andrew J. P.,Williams, David J.,Williamson, Christopher
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p. 15025 - 15044
(2007/10/03)
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- An epoxide derived from D-glucose as the key intermediate for penaresidine and sphingolipids synthesis
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A multigram-scale synthesis of 3R,4R,5R 3,5-dibenzyloxy-4-p- methoxybenzyl-1,2-epoxypentane and its use as intermediate for sphingolipids, penazeridine and penazetidine synthesis are described.
- Beauhaire, Josiane,Ducrot, Paul-Henri
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p. 2443 - 2456
(2007/10/03)
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- Novel asymmetric synthesis of an indolizidine alkaloid, (+)-lentiginosine employing highly stereoselective hydrogenation of α-hydroxypyrrolidine
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An efficient and novel process is described for the asymmetric synthesis of a (1S,2S,8aS)-dihydroxyindolizidine alkaloid, (+)-lentiginosine in which the asymmetric deoxygenation of the quaternary α-hydroxypyrrolidine derivative derived from D-xylose is used as a key step.
- Yoda, Hidemi,Kawauchi, Miho,Takabe, Kunihiko
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p. 137 - 138
(2007/10/03)
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- Synthesis and antiviral evaluation of 2'-deoxy-4'-thio-L-nucleosides and their phosphotriester derivatives bearing S-acyl-2-thioethyl bioreversible phosphate-protecting groups
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A new route to 2-deoxy-4-thio-L-ribofuranose and the synthesis of some 4'-thio-L-nucleosides are reported. Also, the bis(SATE) phosphotriester derivatives of 2'-deoxy-4'-thio-L-cytidine and -adenosine were synthesized and their biological activities are discussed.
- De Valette,Barascut,Imbach
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p. 2289 - 2310
(2007/10/03)
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- Formal synthesis of (-)-syringolide 1 starting from D-xylose based on a biomimetic strategy
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An expeditious and practical synthertic process for a nonproteinaceous elicitor, (-)-syringolide 1, has been developed in a short number of steps utilizing the putative biosynthetic pathway by featuring the elaboration of the protected D-xylose as a starting material.
- Yoda, Hidemi,Kawauchi, Miho,Takabe, Kunihiko,Hosoya, Ken
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p. 1895 - 1898
(2007/10/03)
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- Template-directed intramolecular C-glycosidation. Stereoselective synthesis of bicyclic ketooxetanes from anomeric sulfones
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The Lewis acid-mediated cyclisations of sugar-derived anomeric sulfone-enol ethers 5 and 6 to give respectively the bicyclic ketooxetanes 11/12 and 16/17 are reported.
- Craig, Donald,Tierney, Jason P.,Williamson, Christopher
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p. 4153 - 4156
(2007/10/03)
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- Structure-activity relationship of α-galactosylceramides against b16- bearing mice
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Agelasphin-9b, (2S,3S,4R)-1-O-(α-D-galactopyranosyl)-16-methyl-2-[N- ((R)-2-hydroxytetracosanoyl)-amino]-1,3,4-heptadecanetriol, is a potent antitumor agent isolated from the marine sponge Agelas mauritianus. Various analogues of agelasphin-9b (a lead compound) were synthesized, and the relationship between their structures and biological activities was examined using several assay systems. From the results, KRN7000, (2S,3S,4R)-1-O-(α- D-galactopyranosyl)-2-(N-hexacosanoylamino)-1,3,4-octadecanetriol, was selected as a candidate for clinical application.
- Morita,Motoki,Akimoto,Natori,Sakai,Sawa,Yamaji,Koezuka,Kobayashi,Fukushima
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p. 2176 - 2187
(2007/10/02)
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- Syntheses and conformational studies on AZT and its deuterated analogues
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The NMR spectrum of 3′-azido-3′-deoxythymidine (AZT) in aqueous solution provides sum of some of the proton-proton coupling constants. This limitation precludes the determination of the pseudorotational parameters of the sugar ring. Selective deuteration alleviates this problem. The synthesis of 2′-deutero and 3′-deutero- AZT have been described for the first time starting from D-xylose and β-thymidine respectively. NMR study of these analogues in aqueous solutions shows that almost equal amount of C-2′-endo and C-3′-endo species exist in equilibrium.
- Gurjar,Kunwar,Reddy,Islam,Lalitha,Jagannadh,Rama Rao
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p. 4373 - 4382
(2007/10/02)
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- Preparation of 3'-azido-3'-deoxy-thymidine (AZT) from D-xylose.
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A synthetic route to 3'-azido-3'-deoxy-thymidine (AZT) starting from readily available D-xylose is described.In order to perform complete stereocontrol during the coupling step we decided to prepare the D-xylofuranose synthon 6a bearing a participating group at C-2 and non base-labile protective groups at C-3 and C-5.Thus, further selective deprotection at C-2' of the resulting nucleoside, followed by deoxygenation is straightforward and affords (2'-deoxy-β-D-threo-pentofuranosyl)-thymine 11, a precursor close to AZT.
- Benhaddou, R.,Czernecki, S.,Valery, J. M.,Bellosta, V.
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p. 108 - 111
(2007/10/02)
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- An alternative synthesis of (+)-sesbanimide A
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D-(+)-xylose has been converted to (+)-sesbanimide A in sixteen steps.The synthetic scheme involves an ususual tricyclic silylated derivative (9a) of the monobenzoylated product of the earlier described glutarimide intermediate (7).Compound 9a is a pivotal intermediate for the construction of ring C of (+)-sesbanimide A.
- Vloon, W. J.,Bos, J. C. van den,Willard, N. P.,Koomen, G.-J.,Pandit, U. K.
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p. 414 - 419
(2007/10/02)
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- Ring contraction of 2-O-trifluoromethanesulphonates of α-hydroxy-γ-lactones to oxetane carboxylic esters
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2-O-Trifluoromethanesulphonate esters of the four diastereomeric 3,5-di-O-benzyl-pentono-1,4-lactones gave, on treatment with potassium carbonate in methanol, efficient ring contraction to methyl oxetane-2-carboxylic esters. The stereochemistry at C-2 of
- Witty,Fleet,Vogt,Wilson,Wang,Storer,Myers,Wallis
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p. 4787 - 4790
(2007/10/02)
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- The Synthesis and Reactivity of Cyclic Thiocarbonates Derived from Some Carbohydrate 1,2-Diols
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The attempted synthesis of several carbohydrate 1,2-diols is reported, together with the transformation of two of these diols into cyclic thiocarbonates, namely 4,6-O-benzylidene-3-O-methyl-1,2-O-thiocarbonyl-α-D-glucose and 3,4-O-isopropylidene-1,2-O-thiocarbonyl-β-D-arabinose.The treatment of these thiocarbonates, and a furanose 1,2-thiocarbonate previously prepared by Mukaiyama, with methyl halides and with tributyltin hydride is discussed.A single-crystal X-ray diffraction study of 3,4-O-isopropylidene-1,2-O)-thiocarbonyl-β-D-arabinose is recorded.
- Patroni, Joseph J.,Stick, Robert V.,Tilbrook, D. Matthew G.,Skelton, Brian W.,White, Allan H.
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p. 2127 - 2141
(2007/10/02)
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- EFFICIENT SYNTHESIS AND ANTITUMOR ACTIVITY OF AN ENANTIOMERIC PAIR OF THE SESBANIMIDE AB-RING SYSTEMS
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An enantiomeric pair of the fully unprotected AB-ring systems of sesbanimide A (1), a potent antitumor alkaloid, was efficiently synthesized from readily available D- and L-xylose.Examination on their in vitro antitumor activity clearly disclosed that the AB-ring system only made a small contribution to the notable cytotoxicity of 1.
- Matsuda, Fuyuhiko,Kawasaki, Motojio,Terashima, Shiro
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p. 4639 - 4642
(2007/10/02)
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