- Diesterification of 3-[(β-cyclodextrinyl)succinamido]propane-1,2-diol catalysed by lipase: Diastereoselectivity or tridimensional substrate specificity?
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The transesterification of 3-[(β-cyclodextrinyl)succinamido]propane-1,2-diol with fatty esters catalyzed by immobilized lipase from Mucor miehei occurred with very different conversions of the two diastereoisomers [(R)- or (S)-amidopropanediol]. The highe
- Gervaise, Cédric,Bonnet, Véronique,Nolay, Florian,Cézard, Christine,Stasik, Imane,Sarazin, Catherine,Djeda?ni-Pilard, Florence
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Read Online
- Design, physico-chemical characterization andin vitrobiological activity of organogold(iii) glycoconjugates
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To develop new metal-based glycoconjugates as potential anticancer agents, four organometallic gold(iii)-dithiocarbamato glycoconjugates of the type [AuIII(2-Bnpy)(SSC-Inp-GlcN)](PF6) (2-Bnpy: 2-benzylpyridine; Inp: isonipecotic moie
- Pettenuzzo, Andrea,Vezzù, Keti,Di Paolo, Maria Luisa,Fotopoulou, Eirini,Marchiò, Luciano,Via, Lisa Dalla,Ronconi, Luca
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supporting information
p. 8963 - 8979
(2021/07/02)
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- An alternative and facile synthetic approach for the precursors of 3- and 6-aminosugar donors and study of one-pot glycosyltrasferation
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3- and 6-aminosugars are common motifs in bioactive compounds playing pivotal roles in the bioactivity of the core molecules to which they are attached. However, de novo synthesis of 3- and 6-aminosugars and their corresponding glycosyl donors can be time
- Pandey, Uddav,Prasad Subedi, Yagya,Alfindee, Madher N.,Shepherd, Taylor,Tom Chang, Cheng-Wei
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supporting information
p. 99 - 102
(2020/01/03)
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- An innovative and efficient route to the synthesis of metal-based glycoconjugates: proof-of-concept and potential applications
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With a view to developing more efficient strategies to the functionalization of metallodrugs with carbohydrates, we here report on an innovative and efficient synthetic route to generate gold(iii) glycoconjugates in high yields and purity. The method is based on the initial synthesis of the zinc(ii)-dithiocarbamato intermediate [ZnII(SSC-Inp-GlcN)2] (Inp = isonipecotic moiety; GlcN = amino-glucose) followed by the transfer of the glucoseisonipecoticdithiocarbamato ligand to the gold(iii) center via transmetallation reaction between the zinc(ii) intermediate and K[AuIIIBr4] in 1?:?2 stoichiometric ratio, yielding the corresponding glucose-functionalized gold(iii)-dithiocarbamato derivative [AuIIIBr2(SSC-Inp-GlcN)]. No protection/deprotection of the amino-glucose scaffold and no chromatographic purification were needed. The synthetic protocol was optimized for glucose precursors bearing the amino function at either the C2 or the C6 position, and works in the case of both α and β anomers. The application of the synthetic strategy was also successfully extended to other metal ions of biomedical interest, such as gold(i) and platinum(ii), to obtain [AuI(SSC-Inp-GlcN)(PPh3)] and [PtII(SSC-Inp-GlcN)2], respectively. All compounds were fully characterized by elemental analysis, mid- and far-IR, mono- and multidimensional NMR spectroscopy, and, where possible, X-ray crystallography. Results and potential applications are here discussed.
- Pettenuzzo, Andrea,Montagner, Diego,McArdle, Patrick,Ronconi, Luca
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supporting information
p. 10721 - 10736
(2018/08/17)
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- Facile and Versatile Chemoenzymatic Synthesis of Enterobactin Analogues and Applications in Bacterial Detection
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Siderophores, such as enterobactin (Ent), are small molecules that can be selectively imported into bacteria along with iron by cognate transporters. Siderophore conjugates are thus a promising strategy for delivering functional reagents into bacteria. In this work, we present an easy-to-perform, one-pot chemoenzymatic synthesis of functionalized monoglucosylated enterobactin (MGE). When functionalized MGE is conjugated to a rhodamine fluorophore, which affords RhB-Glc-Ent, it can selectively label Gram-negative bacteria that utilize Ent, including some E. coli strains and P. aeruginosa. V. cholerae, a bacterium that utilizes linearized Ent, can also be weakly targeted. Moreover, the targeting is effective under iron-limiting but not iron-rich conditions. Our results suggest that the RhB-Glc-Ent probe is sensitive not only to the bacterial strain but also to the iron condition in the environment.
- Lee, Albert A.,Chen, Yi -Chen S.,Ekalestari, Elisa,Ho, Sheng -Yang,Hsu, Nai -Shu,Kuo, Tang -Feng,Wang, Tsung -Shing Andrew
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supporting information
p. 12338 - 12342
(2016/10/13)
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- Linear poly(amide triazole)s derived from d -glucose
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The click reaction between azides and alkynes is been increasingly employed in the preparation of polymers. In this article, we describe the synthesis and click polyaddition reaction of a new A-B-type amide monomer - prepared from d-glucose as renewable r
- Molina-Pinilla, Inmaculada,Bueno-Martinez, Manuel,Hakkou, Khalid,Galbis, Juan A.
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p. 629 - 638
(2014/02/14)
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- Synthesis and glycosidase inhibitory profiles of functionalised morpholines and oxazepanes
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In this work libraries of morpholines and oxazepanes have been prepared via the reductive amination reaction between dialdehydes, derived from carbohydrates, and a range of amines. In this way, functionalised morpholines and oxazepanes have been prepared
- Burland, Peter A.,Osborn, Helen M.I.,Turkson, Andrea
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experimental part
p. 5679 - 5692
(2011/10/31)
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- Quantifying the electronic effects of carbohydrate hydroxy groups by using aminosugar models
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Methyl amino-deoxy-glycosides with α- and β-gluco, α-galacto, or α-manno stereochemistry with the amino functionality in each of the four possible non-anomeric positions have been synthesized and their pKa values determined by titration. These
- Pedersen, Christian M.,Olsen, Jacob,Brka, Azra B.,Bols, Mikael
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p. 7080 - 7086
(2011/07/08)
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- Synthesis and antibacterial activity of aminodeoxyglucose derivatives against Listeria innocua and Salmonella typhimurium
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In this study aminodeoxyglucose derivatives were synthesized and evaluated for their antibacterial activity against two food bacteria, Listeria innocua and Salmonella typhimurium. 6-Amino-6-deoxy-α-Dmethylglucopyranose (GSA-6), 3-amino-3-deoxy-D-glucopyranoside (GSA-3), and β-D-glucopyranosylamine (GSA-1) were synthesized and concurrently tested with commercially available D-glucosamine (GSA-2) for antibacterial activity. Results obtained from this study showed a pronounced antagonist effect due to the position of amino groups of aminoglucose derivatives on the antibacterial activity. GSA-3 was the most active compound. At a concentration of 2 × 10 -4 mol mL -1, it delayed the growth of both bacteria with percentages of inhibition of 29 and 15% for L. innocua and S. typhimurium, respectively. At the same concentration the percentages of inhibition for other aminodeoxyglucoses varied between 5 and 18% and between 2 and 11% for L. innocua and S. typhimurium, respectively. All compounds were characterized by FTIR, 1H NMR, and 13C NMR spectroscopy.
- Theoneste, Muhizi,Stephane, Greller,Veronique, Coma
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experimental part
p. 8770 - 8775
(2010/07/17)
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- METHODS, COMPOUNDS, COMPOSITIONS AND VEHICLES FOR DELIVERING 3-AMINO-1-PROPANESULFONIC ACID
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The invention relates to methods, compounds, compositions and vehicles for delivering 3-amino-1-propanesulfonic acid (3APS) in a subject, preferably a human subject. The invention encompasses compounds that will yield or generate 3APS, either in vitro or in vivo. Preferred compounds include amino acid prodrugs of 3APS for use, including but not limited to, the prevention and treatment of Alzheimer's disease.
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Page/Page column 49-50
(2008/12/06)
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- Model for antibiotic optimization via neoglycosylation: Synthesis of liponeoglycopeptides active against VRE
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The neoglycosylation of a methoxyamine-appended vancomycin aglycon with all possible N′-decanoylglucopyranose and N′-biphenoylglucopyranose regioisomers led to the production of a focused set of liponeoglycopeptide variants in good yields and with excellent stereoselectivity. High-throughput antibacterial assays employing a unique set of vancomycin-resistant Enterococci faecalis and Enterococci faecium clinical isolates revealed that the nature and regiochemistry of glycosyl lipidation modulated vancomycin-resistent Enterococci potency. In contrast to prior work with lipoglycopeptides, this study reveals the glucose C3′ or C4′ as the optimal position for neoglycopeptide lipidation. This purely chemical method for the diversification of the glycolipid portion of lipoglycopeptide antibiotics is simple to perform on a large scale, requires minimal synthetic effort in sugar donor preparation, and provides access to highly active antibiotics that are not easily prepared by other state-of-the-art methods.
- Griffith, Byron R.,Krepel, Candace,Fu, Xun,Blanchard, Sophie,Ahmed, Aqeel,Edmiston, Charles E.,Thorson, Jon S.
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p. 8150 - 8155
(2008/02/11)
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- Novel drug delivery compositions
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The present invention provides for a novel molecules useful for delivery of compounds to a mammal, more particularly for the intracellular delivery of nucleotides, nucleotide analogues or compounds with a heterocyclic base. Also provided for are novel therapeutic complexes comprising novel molecules complexed with nucleotide analogues or heterogeneous or homogenous oligomers comprised of nucleotide analogues.
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Page/Page column 13
(2010/11/25)
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- A safe and convenient method for the preparation of triflyl azide, and its use in diazo transfer reactions to primary amines
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A safe and convenient method for the copper(II)-catalyzed diazo transfer from triflyl azide to primary amines is reported. By replacing CH2Cl2 by toluene the formation of hazardous side products, for example, azido-chloromethane and diazidomethane can be avoided.
- Titz, Alexander,Radic, Zorana,Schwardt, Oliver,Ernst, Beat
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p. 2383 - 2385
(2007/10/03)
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- Sonochemistry: A powerful way of enhancing the efficiency of carbohydrate synthesis
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Using sonication as a means of facilitating organic reactions in carbohydrate chemistry was explored under the conditions used for traditional organic synthesis. An array of representative reactions, including hydroxy group manipulation (acylation, protection/deprotection, acyl group migration), thioglycoside synthesis, azidoglycoside synthesis, 1,3-dipolar cycloaddition and reductive cleavage of benzylidene, commonly used in the synthesis of carbohydrate derivatives was examined. A series of glycosylation reactions that employ thioglycosides, glycosyl trichloroacetimidate, glycosyl bromide and glycosyl acetate as the glycosyl donors was also examined. Our results demonstrate that sonication can significantly shorten the reaction time, enhance the reactivity of reactant and lead to superior yield and excellent stereoselectivity. More importantly, a general protocol of glycosylation may finally be developed. Sonication is compatible to the conditions used for traditional organic synthesis. We believe that sonication can also be applied to other areas of synthetic processes.
- Deng, Shenglou,Gangadharmath, Umesh,Chang, Cheng-Wei Tom
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p. 5179 - 5185
(2007/10/03)
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- New glycoconjugated cyanine dyes as fluorescent labeling reagents
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New highly water soluble cyanine dyes incorporating methyl glucopyranoside residues and reactive functionality are synthesised. The new dyes are conjugated to aminodextrans and to antibodies. The absorption and fluorescence properties of the new dyes and of the labeled substrates are discussed.
- Reddington, Mark V.
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p. 143 - 147
(2007/10/03)
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- Synthesis and surface-active properties of amphiphilic 6-aminocarbonyl derivatives of D-glucose
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Several 6-amido-6-deoxy derivatives of methyl α-D-glucopyranoside and D-glucopyranose were prepared via peracetylated 6-azido-6-deoxy or 6-deoxy-6-isocyanato intermediates. These compounds displayed high Krafft temperatures which could result from hydrogen bonding between NH and O-5. Their tensio-active properties above the Krafft temperature were compared with Hecameg (methyl 6-O-(N-heptylcarbamoyl)-α-D-glucopyranoside).
- Maunier, Valerie,Boullanger, Paul,Lafont, Dominique,Chevalier, Yves
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- A mild one-step selective conversion of primary hydroxyl groups into azides in mono- and oligo-saccharides
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The direct azidation reaction of several monosaccharide methyl glycopyranosides, sucrose, α,α-trehalose, cyclomaltohexaose and cyclomaltoheptaose with sodium azide in the presence of triphenylphosphine-carbon tetrabromide is reported. The optimal reaction conditions require pre-formation of the reactive species before addition of the sugar substrate. Formation of the primary azidodeoxy compound is accompanied by simultaneous formation of the corresponding primary bromodeoxy and 3,6-anhydro derivatives in the glycopyranoside series, the former being transformed in situ into the azide by quenching of the reaction mixture with methanol before increasing the temperature. Interestingly, good selectivity towards the primary C-6 position of the glucopyranosyl moiety as compared to the fructofuranosyl one was observed in the case of sucrose, advantage of which has been taken in an improved preparation of 2,3,4,1',3',4',6'-hepta-O-acetyl-6-azido-6-deoxysucrose (45% yield from sucrose). Sodium or lithium azide reagents were found equally effective. The azide functionality could be reduced without previous purification and the resulting amino sugar isolated by cation-exchange column chromatography, as illustrated for the preparation of 6(I)-amino-6(I)-deoxycyclomaltoheptaose.
- Jimenez Blanco, Jose Luis,Garcia Fernandez, Jose Manuel,Gadelle, Andree,Defaye, Jacques
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p. 367 - 372
(2007/10/03)
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