- Anti-norovirus activity of C7-modified 4-amino-pyrrolo[2,1-f][1,2,4]triazine C-nucleosides
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Synthetic nucleoside analogues characterized by a C–C anomeric linkage form a family of promising therapeutics against infectious and malignant diseases. Herein, C-nucleosides comprising structural variations at the sugar and nucleobase moieties were exam
- Groaz, Elisabetta,Herdewijn, Piet,Li, Qingfeng,Neyts, Johan,Rocha-Pereira, Joana
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- Bicyclic 1-Azafagomine Derivatives: Synthesis and Glycosidase Inhibitory Testing
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The synthesis of a series of 1-azafagomine derivatives that are tethered with five- and six-membered 1,2-annulated ring systems is described. These compounds were used in order to explore whether a hydrogen-bond acceptor group on the carbon atom corresponding to the glycosidic oxygen is able to interact with the catalytic acidic residue of β-glucosidase. The hydrogen-bond acceptor group was installed at various positions on the annulated ring system making it possible to study the effect of altering the position of this group.
- Evangelista, Tereza C. Santos,Ferreira, Sabrina Baptista,Sydnes, Magne O.,Fernández-Bola?os, José G.,Lindb?ck, Emil,Lopéz, óscar
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p. 4066 - 4077
(2019/10/28)
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- Chemical Synthesis of Ketopentose-5-phosphates
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A chemical synthesis of ketopentose-5-phosphates that are involved in the pentose phosphate pathway has been developed. The ketopentose phosphates, d-ribulose-5-phosphate and d-xylulose-5-phosphate, were prepared in five steps starting from known intermed
- Wei, Wei-Chih,Chang, Che-Chien
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p. 3033 - 3040
(2017/06/20)
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- Synthesis of d -Fagomine and Its Seven- and Eight-Membered Higher-Ring Analogues, and the Formal Synthesis of (+)-Australine from l -Xylose-Derived Chiron
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The synthesis of d-fagomine and its seven- and eight-membered higher-ring analogues from commercially available l-xylose is reported. The syntheses involve elaboration of a common alkenol precursor obtained from l-xylose-derived hemiacetal. The key steps
- Das, Pintu,Ajay, Sama,Shaw, Arun K.
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p. 3753 - 3762
(2016/11/08)
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- Synthesis and evaluation of: N -alkylated analogues of aza-galacto-fagomine-potential pharmacological chaperones for Krabbe disease
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Seven novel alkylated or acylated analogues of hexahydropyridazine aza-galacto-fagomine (AGF) was prepared and studied as glycosidase inhibitors with the aim of increasing inhibitory potency and selectivity. The enzyme galactocerebrosidase, implicated in Krabbe disease, was found to be potently inhibited by n-butyl N2-alkylated AGF.
- Viuff, Agnete H.,Jensen, Henrik H.
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p. 8545 - 8556
(2016/09/28)
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- Synthetic Study on Carthamin: Problem and Solution for Oxidative Dearomatization Approach to Quinol C -Glycoside
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Synthetic study on carthamin, a natural red pigment, is described. Attempts at the construction of the key quinol C-glycoside structure by oxidative dearomatization of C-glycosyl phenols were hampered by the competing cleavage of the C1-C2 bond in the sugar moiety. By employing the 2-O-acetyl protection, the projected reaction proceeded smoothly, giving the desired products in good to excellent yields. An interesting photochemical stability/instability of the chalcone geometry in the synthetic compounds was observed.
- Hayashi, Taiki,Ohmori, Ken,Suzuki, Keisuke
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supporting information
p. 2345 - 2351
(2016/09/28)
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- METHOD FOR PRODUCING THIOLANE SKELETON-TYPE GLYCOCONJUGATE, AND THIOLANE SKELETON-TYPE GLYCOCONJUGATE
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PROBLEM TO BE SOLVED: To provide a simplified method for producing a synthetic intermediate of a thionucleoside in high yield under a moderate condition by a reaction to form a thiolane ring. SOLUTION: The present invention relates to a method for produci
- -
-
Paragraph 0210-0212
(2016/10/08)
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- Iodine monochloride (ICl) as a highly efficient, green oxidant for the oxidation of alcohols to corresponding carbonyl compounds
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Iodine monochloride (ICl) was discovered to be a highly efficient, green oxidant, which can oxidize aldose hemiacetals, diarylmethanols, arylalkylmethanols, anddialkylmethanols to the corresponding aldose lactones, diarylmethanones, arylalkylmethanones, and dialkylmethanones, respectively, in high yields. ICl as a green, metal-free oxidant is characterized by mild reaction condition, short reaction time, good yield, and broad scope.
- Wei, Peng,Zhang, Datong,Gao, Zhigang,Cai, Wenqing,Xu, Weiren,Tang, Lida,Zhao, Guilong
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supporting information
p. 1457 - 1470
(2015/05/20)
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- Azasugar inhibitors as pharmacological chaperones for Krabbe disease
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Krabbe disease is a devastating neurodegenerative disorder characterized by rapid demyelination of nerve fibers. This disease is caused by defects in the lysosomal enzyme β-galactocerebrosidase (GALC), which hydrolyzes the terminal galactose from glycosphingolipids. These lipids are essential components of eukaryotic cell membranes: substrates of GALC include galactocerebroside, the primary lipid component of myelin, and psychosine, a cytotoxic metabolite. Mutations of GALC that cause misfolding of the protein may be responsive to pharmacological chaperone therapy (PCT), whereby small molecules are used to stabilize these mutant proteins, thus correcting trafficking defects and increasing residual catabolic activity in cells. Here we describe a new approach for the synthesis of galacto-configured azasugars and the characterization of their interaction with GALC using biophysical, biochemical and crystallographic methods. We identify that the global stabilization of GALC conferred by azasugar derivatives, measured by fluorescence-based thermal shift assays, is directly related to their binding affinity, measured by enzyme inhibition. X-ray crystal structures of these molecules bound in the GALC active site reveal which residues participate in stabilizing interactions, show how potency is achieved and illustrate the penalties of aza/iminosugar ring distortion. The structure-activity relationships described here identify the key physical properties required of pharmacological chaperones for Krabbe disease and highlight the potential of azasugars as stabilizing agents for future enzyme replacement therapies. This work lays the foundation for new drug-based treatments of Krabbe disease.
- Hill, Chris H.,Viuff, Agnete H.,Spratley, Samantha J.,Salamone, Stéphane,Christensen, Stig H.,Read, Randy J.,Moriarty, Nigel W.,Jensen, Henrik H.,Deane, Janet E.
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p. 3075 - 3086
(2015/09/08)
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- PYRROLIDINE DERIVATIVES AS SELECTIVE GLYCOSIDASE INHIBITORS AND USES THEREOF
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Disclosed are compounds of formula (I): or a pharmaceutically acceptable salt, derivative, solvate, isomer, tautomer, N-oxide, ester, prodrug, isotope or protected form thereof, which are of use as OGA inhibitors, for example in the treatment of various conditions and diseases, including neurodegenerative disorders.
- -
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Paragraph 0377; 0380
(2014/03/25)
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- PYRROLIDINE DERIVATIVES AS SELECTIVE GLYCOSIDASE INHIBITORS AND USES THEREOF
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Disclosed are compounds of formula (I) or a pharmaceutically acceptable salt, derivative, solvate, isomer, tautomer, N-oxide, ester, prodrug, isotope or protected form thereof, which are of use as OGA inhibitors, for example in the treatment of various conditions and diseases, including neurodegenerative disorders
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Page/Page column 90-91
(2012/09/21)
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- An expeditious synthesis of an analogue of (-)-steviamine by way of the 1,3-dipolar cycloaddition of a nitrile oxide with a 1-C-allyl iminosugar
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In our continuing effort to develop inhibitors of the mycobacterial galactan biosynthesis, we planned to synthesize original iminosugar-based analogues of UDP-galactofuranose by way of the 1,3-dipolar cycloaddition reaction between a 1-C-allyl iminosugar and a nitrile oxide, followed by the reductive cleavage of the resulting isooxazoline. In initial studies, it was found that this last step led in one pot to a new poly-hydroxylated indolizidine derivative closely related to the recently isolated (-)-steviamine, in good yield, by way of a sequence involving at least five individual reactions. The activity of this new compound as a glycosidase inhibitor was evaluated against a panel of glycosidases and compared to (-)-steviamine.
- Chronowska, Aleksandra,Gallienne, Estelle,Nicolas, Cyril,Kato, Atsushi,Adachi, Isao,Martin, Olivier R.
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scheme or table
p. 6399 - 6402
(2011/12/22)
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- Mild and efficient chemoselective deprotection of anomeric O-methyl glycosides with trityl tetrafluoroborate
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(Chemical Equation Presented) A facile chemoselective deprotection of anomeric O-methyl glycosides has been achieved in good to excellent yields within 10-40 min with use of trityl tetrafluoroborate in dichloromethane at ambient temperatures. The present method is easily implemented and tolerates different functional groups.
- Kumar, Amit,Doddi, Venkata Ramana,Vankar, Yashwant D.
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p. 5993 - 5995
(2008/12/21)
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- Total synthesis of (+)-hyacinthacine A2 based on SmI 2-induced nitrone umpolung
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(Chemical Equation Presented) A concise total synthesis of (+)-hyacinthacine A2, a polyhydroxylated pyrrolizidine alkaloid, is described using our recently discovered inversion of the C-N bond polarity in nitrones. In the key step, the diastere
- Desvergnes, Stephanie,Py, Sandrine,Vallee, Yannick
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p. 1459 - 1462
(2007/10/03)
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- Total syntheses of hyacinthacine A2 and 7-deoxycasuarine by cycloaddition to a carbohydrate derived nitrone
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Practical syntheses of nitrone 8 by two different approaches from sugars are reported. Its use as a versatile intermediate in highly selective 1,3-dipolar cycloaddition reactions constitutes the key step for novel total syntheses of hyacinthacine A2
- Cardona, Francesca,Faggi, Enrico,Liguori, Francesca,Cacciarini, Martina,Goti, Andrea
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p. 2315 - 2318
(2007/10/03)
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- Synthesis of 6-deoxy-homoDMDP and its C(5)-epimer: Absolute stereochemistry of natural products from Hyacinthus orientalis
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A concise enantioselective synthesis of 2,5-imino-2,5,6-trideoxy-D-manno-heptitol (6-deoxy-homoDMDP) and 2,5-imino-2,5,6-trideoxy-L-gulo-heptitol has been achieved. These compounds were used as stereochemical references to establish the absolute configuration of the corresponding naturally occurring stereoisomers, recently isolated from Hyacinthus orientalis.
- Behr, Jean-Bernard,Guillerm, Georges
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p. 111 - 113
(2007/10/03)
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- A facile and rapid route to a new series of pyrrolizidines structurally related to (+)-alexine and (+)-australine
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Addition of allylmagnesium chloride to protected L-xylofuranosylamine gave, after intramolecular cyclization, the corresponding polyhydroxylated 2-allylpyrrolidines. New series of analogues of (+)-alexine and (+)-australine were readily obtained from these intermediates by dihydroxylation, intramolecular nucleophilic displacement and subsequent deprotection. The determination of the configuration at the newly formed stereocentres was based on NMR experiments. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
- Behr, Jean-Bernard,Erard, Audrey,Guillerm, Georges
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p. 1256 - 1262
(2007/10/03)
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- Synthesis and biological evaluation of water soluble taxoids bearing sugar moieties
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Synthesis and biological evaluation of a variety of water soluble taxoids with sugar moieties are described.
- Mandai, Tadakatsu,Okumoto, Hiroshi,Oshitari, Tetsuta,Nakanishi, Katsuyoshi,Mikuni, Katsuhiko,Hara, Ko-ji,Hara, Ko-zo,Iwatani, Wakao,Amano, Tetsuya,Nakamura, Kosho,Tsuchiya, Yoshinori
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p. 561 - 566
(2007/10/03)
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- An olefin metathesis route for the preparation of (1 → 6)-linked C-disaccharide glycals. A convergent and flexible approach to C-saccharide synthesis
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A convergent route to a variety of C-1-disaccharide glycals based on the olefin metathesis reaction of enol ethers and alkenes is described. The DCC-mediated coupling reaction of a variety of pentose enitols (1a-c) with a number of C-5- and C-6-monosaccharide carboxylic acids (2a-e) gave the corresponding esters 3a-1 in good yield. Methylenation of these compounds was followed by ring-closing metathesis, mediated by the Schrock molybdenum catalyst 8 in warm toluene, to provide the target C-disaccharide glycals 5a-1. The formed enol ether double bond in 5a was then transformed, via standard manipulations, into a variety of C-disaccharide derivatives 21-25.
- Postema, Maarten H. D.,Calimente, Daniel,Liu, Lei,Behrmann, Tonja L.
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p. 6061 - 6068
(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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- Total Syntheses of De-branched Nagstatin and Its Analogs Having Glycosidase Inhibiting Activities
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De-branched nagstatin and its analogs have been synthesized from protected L-ribo- and xylo-furanoses through the inter- and intra-molecular nucleophilic reactions with the imidazole moieties.
- Tatsuta, Kuniaki,Miura,Shozo,Ohta, Shigeru,Gunji, Hiroki
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p. 1085 - 1088
(2007/10/02)
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- Immunostimulatory and antitumor activities of monoglycosylceramides having various sugar moieties
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Ten kinds of monoglycosylceramides (MonoCers), having the same ceramide portion and different sugar moieties, were synthesized and their immunostimulatory and antitumor activities were examined. The manner of combination between sugar and ceramide has been demonstrated to affect the manifestation of immunostimulatory and resultant antitumor activities of MonoCers, and in the case of D-MonoCers having the D-sugar, α-D-MonoCers (sugar combined to ceramide in an α-configuration) show stronger activities than β-D-MonoCers. Furthermore, the form of sugar, not the furanose-form but the pyranose-form, and the 2- and 4-hydroxyl groups of the pyranose-form of sugar, seemed to play an important role in the manifestation of the activities of α-D-MonoCers.
- Motoki,Morita,Kobayashi,Uchida,Akimoto,Fukushima,Koezuka
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p. 1487 - 1491
(2007/10/03)
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- C-glycofuranosides via tandem Wittig-Michael sequence using a thiazole-armed phosphorane. A route to C-furanosyl α-hydroxy propanals and propionic acids
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The reactions of 2-thiazolylcarbonylmethylenetriphenylphosphorane with five protected D-furanoses (manno, ribo, arabino, xylo, and lyxo) in refluxing toluene lead to mixtures of α- and β-1-C-(2-thiazolacyl)-glycosides (66-93 % overall yield). The β-linked C-glycosides derived from 2,3:5,6-di-O-isopropylidene-D-mannnofuranose was reduced to (R) and (S) akohols which after protection as O-benzyl ethers were transformed to α-alkoxy aldehydes by thiazole-to-formyl conversion; the aldehydes were oxidized to the corresponding α-alkoxy acids.
- Dondoni, Alessandro,Marra, Alberto
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p. 7327 - 7330
(2007/10/02)
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- Synthesis of a spacer-containing trimeric fragment of the capsular polysaccharide from Escherichia coli K100
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Stereoselective β-glycosidation of 1,3,4-tri-O-benzyl-5-O-pivaloyl-D-ribitol, prepared from L-ribose, with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose gave, after protecting-group manipulations, the properly protected terminal and non-terminal units.Elongation (2*) of the terminal unit with the incoming non-terminal unit could be acomplished using the bifunctional phosphorylating reagent, bis(1-benzotriazolyl) 2-chlorophenyl phosphate.The trimeric unit thus obtained was condensed, using the same phosphorylating reagent, with the spacer N2-(benzyloxycarbonyl)-N1-(3-hydroxypropyl)glycinamide, to give, after complete deblocking, the spacer-containing trimeric unit of Escherichia coli K100.
- Elie, C. J. J.,Hoogerhout, P.,Muntendam, H. J.,Werken, G. van de,Marel, G. A. van der,Boom, J. H. van
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p. 467 - 473
(2007/10/02)
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- POTENT COMPETITIVE INHIBITION OF &α-GALACTOSIDASE AND &α-GLUCOSIDASE ACTIVITY BY 1,4-DIDEOXY-1,4-IMINOPENTITOLS: SYNTHESES OF 1,4-DIDEOXY-1,4-IMINO-D-LYXITOL AND OF BOTH ENANTIOMERS OF 1,4-DIDEOXY-1,4-IMINOARABINITOL
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The syntheses of 1,4-dideoxy-1,4-imino-D-lyxitol (3), 1,4-dideoxy-1,4-imino-D-arabinitol (4) and 1,4-dideoxy-1,4-imino-L-arabinitol (5) are reported; (3) is a potent competitive inhibitor of α-galactosidase (green coffee beans) and (4) a competitive inhibitor of α-glucosidase (Brewer's yeast) suggesting that iminopentitols have considerable potential as glycosidase inhibitors. (4) was found to be identical to an alkaloid recently isolated from Angylocalyx boutiqueanus.
- Fleet, G. W. J.,Nicholas, S. J.,Smith, P. W.,Evans, S. V.,Fellows, L. E.,Nash, R. J.
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p. 3127 - 3130
(2007/10/02)
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- Synthesis of benzyl and allyl ethers of D-glucopyranose
-
Starting from allyl 3-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside as a key intermediate, the following crystalline compounds were prepared: 2-O-allyl-3,4,6-tri-O-benzyl-D-glucopyranose (11) and its p-nitrobenzoate; 2,3,5-tri-O-benzyl-D-arabinofuranose (12) and the corresponding arabinitol; allyl 3,4,6-tri-O-benzyl-α-D-glucopyranoside (7); 3,4,6-tri-O-benzyl-D-glucopyranose (8); 2-O-allyl-3,4-di-O-benzyl-D-glucopyranose (17) and its bis(p-nitrobenzoate); and 3,4-di-O-benzyl-D-glucopyranose (19). The p-nitrobenzoates of compounds 11 and 17 are potential intermediates for the synthesis of the glycolipids of the cytoplasmic membranes of Streptococci.
- Gent, Patricia A.,Gigg, Roy
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p. 325 - 333
(2007/10/10)
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