- 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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- Synthetic development of sugar amino acid oligomers towards novel podophyllotoxin analogues
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In this work, we have developed an approach for the synthesis of sugar amino acid oligomers based on the glucosamine scaffold. We found that the solid-phase approach was unsuccessful for the preparation of sugar amino acid oligomers and the limitation of
- Bouchard, Megan,Tremblay, Thomas,Paré-Lacroix, Marie-Pier,Gagné-Boulet, Mathieu,Fortin, Sébastien,Giguère, Denis
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- Ultrasonication-Assisted Synthesis of a d-Glucosamine-Based β-CD Inclusion Complex and Its Application as an Aqueous Heterogeneous Organocatalytic System
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For the first time, an inclusion complex has been crafted between a carbohydrate-based molecule and a β-cyclodextrin (CD) hydrophobic cavity for asymmetric catalytic applications. This novel d-glucosamine-based inclusion compound has been synthesized in h
- Rani, Dhiraj,Sethi, Aaftaab,Kaur, Khushwinder,Agarwal, Jyoti
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p. 9548 - 9557
(2020/09/09)
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- Ring-Opening Reactions of the N-4-Nosyl Hough-Richardson Aziridine with Nitrogen Nucleophiles
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Dinosylated α-d-glucopyranoside was directly transformed into α-d-altropyranosides via in situ formed N-4-nosyl Hough-Richardson aziridine with nitrogen nucleophiles under mild conditions in fair to excellent yields. The scope of the aziridine ring-opening reaction was substantially broadened contrary to the conventional methods introducing solely the azide anion at high temperatures. If necessary, the N-4-nosyl Hough-Richardson aziridine can be isolated by filtration in a very good yield and high purity.
- Ru?il, Tomá?,Trávní?ek, Zdeněk,Canka?, Petr
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p. 723 - 730
(2017/04/26)
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- Sugar derived alkamine catalytic imine reduction method
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The invention discloses a method used for catalytic reduction of imine with saccharide-derivatized amino alcohol. According to the method, imine is taken as a substrate. The method comprises following steps: 1) imine and saccharide-derivatized amino alcohol are dissolved in an organic solvent I, wherein molar ratio of imine to saccharide-derivatized amino alcohol ranges from 100:1-20; 2) trichlorosilane with 1.5 to 5 times equivalent weights is added into a solution obtained via step 1) dropwise, an obtained mixture is stirred and reacted for 12 to 36h at a temperature of -20 to 40 DEG C, and a saturated sodium bicarbonate solution is used for quenching; 3) a material obtained via step 2) is extracted with an organic solvent II, and is subjected to column chromatography isolation so as to obtain amine compounds.
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Paragraph 0035; 0036; 0037
(2016/10/07)
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- Synthetic heparin pentasaccharides
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Preparation and use of synthetic monosaccharides, disaccharides, trisaccharides, tetrasaccharides and pentasaccharides useful for the preparation of synthetic heparinoids.
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Page/Page column 36; 37
(2016/02/12)
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- N-acetylgalactosamine green synthetic method
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The present invention discloses a N-acetylgalactosamine green synthetic method. According to the method, N-acetylglucosamine as a raw material is successively condensed with an alcohol and pivaloyl chloride, and then N-acetylgalactosamine can be obtained
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Paragraph 0037; 0038
(2016/11/28)
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- Glucosamine-based primary amines as organocatalysts for the asymmetric aldol reaction
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Glucosamine derivatives have been synthesized starting from commercially available N-acetyl-D-glucosamine/glucosamine hydrochloride and have been employed successfully as efficient organocatalysts for the direct asymmetric aldol reaction between cyclohexa
- Agarwal, Jyoti,Peddinti, Rama Krishna
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scheme or table
p. 3502 - 3505
(2011/06/21)
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- Oligo-Aminosaccharide compound
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An oligo-aminosaccharide compound formed by binding 3 to 6 saccharides, such as 2,6-diamino-2,6-dideoxy-α-(1→4)-D-glucopyranose oligomers, or a salt thereof, which has high affinity to a double-stranded nucleic acid.
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Page/Page column 8
(2011/01/12)
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- Synthesis and characterization of d-glucosamine-derived low molecular weight gelators
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Carbohydrate-based low molecular weight gelators are an interesting class of molecules with many potential applications. Previously, we have found that certain esters and carbamates of 4,6-O-benzylidene-α-d-methyl- glucopyranoside are low molecular weight
- Goyal, Navneet,Cheuk, Sherwin,Wang, Guijun
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supporting information; experimental part
p. 5962 - 5971
(2010/09/18)
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- Accessible sugars as asymmetric olefin epoxidation organocatalysts: Glucosaminide ketones in the synthesis of terminal epoxides
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A systematically varied series of conformationally restricted ketones, readily prepared from N-acetyl-d-glucosamine, were tested against representative olefins as asymmetric epoxidation catalysts showing useful selectivities against terminal olefins and, in particular, typically difficult 2,2-disubstituted terminal olefins.
- Boutureira, Omar,McGouran, Joanna F.,Stafford, Robert L.,Emmerson, Daniel P. G.,Davis, Benjamin G.
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supporting information; experimental part
p. 4285 - 4288
(2009/12/05)
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- Synthesis of Tc-99m labeled glucosamino-Asp-cyclic(Arg-Gly-Asp-d-Phe-Lys) as a potential angiogenesis imaging agent
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Angiogenesis imaging agents for single photon emission computed tomography (SPECT) play a role in diagnosing tumor-induced angiogenesis as well as tumor metastasis. We synthesized and evaluated radiolabeled RGD glycopeptides by incorporation of the [
- Lee, Byung Chul,Sung, Hyun Ju,Kim, Ji Sun,Jung, Kyung-Ho,Choe, Yearn Seong,Lee, Kyung-Han,Chi, Dae Yoon
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p. 7755 - 7764
(2008/03/28)
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- A 1-acetamido derivative of 6-epi-valienamine: An inhibitor of a diverse group of β-N-acetylglucosaminidases
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The synthesis of an analogue of 6-epi-valienamine bearing an acetamido group and its characterisation as an inhibitor of β-N- acetylglucosaminidases are described. The compound is a good inhibitor of both human O-GlcNAcase and human β-hexosaminidase, as well as two bacterial β-N-acetylglucosaminidases. A 3-D structure of the complex of Bacteroides thetaiotaomicron BtGH84 with the inhibitor shows the unsaturated ring is surprisingly distorted away from its favoured solution phase conformation and reveals potential for improved inhibitor potency. This journal is The Royal Society of Chemistry.
- Scaffidi, Adrian,Stubbs, Keith A.,Dennis, Rebecca J.,Taylor, Edward J.,Davies, Gideon J.,Vocadlo, David J.,Stick, Robert V.
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p. 3013 - 3019
(2008/04/01)
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- Precise structure activity relationships in asymmetric catalysis using carbohydrate scaffolds to allow ready fine tuning: dialkylzinc-aldehyde additions.
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The ready construction of 24 stereochemically and functionally diverse carbohydrate ligand structures from a core D-glucosamine scaffold has allowed the evaluation of broad ranging structure activity relationships in ligand accelerated zincate additions t
- Emmerson, Daniel P G,Villard, Renaud,Mugnaini, Claudia,Batsanov, Andrei,Howard, Judith A K,Hems, William P,Tooze, Robert P,Davis, Benjamin G
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p. 3826 - 3838
(2007/10/03)
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- Preparation and Properties of New Surfactants Containing D-Glucosamine as the Building Block
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Three types of new surfactants were prepared by using N-acetyl-D-glucosamine as a starting material.The first type of surfactant, sodium methyl 4,6-O-alkylidene-2-(carboxylatomethylamino)-2-deoxy-D-glucopyranoside, was prepared successively by the following treatments: methyl glucosidation of N-acetyl-D-glucosamine, transacetalization with an appropriate aldehyde dimethyl acetal, deacetylation, and finally reaction of the resulting methyl-4,6-O-alkylidene-2-amino-2-deoxy-D-glucopyranoside (2-amino precursor) with bromoacetic acid.The reaction of this 2-amino precursor with methyl iodide yielded the second type of surfactant, methyl 4,6-O-alkylidene-2-deoxy-2(trimethylammonio)-D-glucopyranoside iodide, in excellent yield.The last type of compound, sodium methyl 2-acetamide-4,6-O-alkylidene-3-O--2-deoxy-D-glucopyranoside, was synthesized by the reaction of methyl 2-acetamide-4,6-O-alkylidene-2-deoxy-D-glucopyranoside with 2-chloropropionic acid.Concerning the two carboxylate types of surfactants, the compounds containing a C9 or C11 hydrophobic chain in the alkylidene part showed higher water solubility than the corresponding compounds containing a C7 hydrophobic chain.Both the micelle-forming property and the ability to lower the surface tension of these carboxylate types of compounds increased with an increase in the length of the hydrophobic chain in the alkylidene part.These compounds can be applied to new acid-decomposable types of cleavable surfactants because they contain an acetal group.The acetal bond of the ammonium type of compound was cleaved more slowly than that of the corresponding carboxylate types of surfactants in 2percent aqueous HCl solution.The biodegradabilities of these compounds were also determined.KEY WORDS: Acetalization, acid decomposition properties, biodegradability, D-glucosamine, surface-active properties.
- Kida, Toshiyuki,Yurugi, Keiji,Masuyama, Araki,Nakatsuji, Yohji,Ono, Daisuke,Takeda, Tokuji
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p. 773 - 780
(2007/10/03)
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- Marine natural products. XXVIII. The structures of sarasinosides A1, A2, A3, B1, B2, B3, C1, C2, and C3, nine new norlanostane-triterpenoidal oligoglycosides from the palauan marine sponge Asteropus sarasinosum
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The chemical structures of sarasinosides A1, A2, A3, B1, B2, B3, C1, C2, and C3, nine 30-norlanostane-triterpenoidal oligoglycosides isolated from the Palauan marine sponge Asteropus sarasinosum have been elucidated on the basis of chemical and physicochemical evidence. Sarasinosides A2 (2) and A3 (3) were shown to he the 7,9(11)-diene and 8,14-diene analogs of sarasinoside A1 (1), whereas sarasinosides B2 (7) and B3 (9) were the 7,9(11)-diene and 8,14-diene analogs of sarasinoside B1 (5), respectively. Similar structural correlations of sarasinosides C2 (6) and C3 (8) with sarasinoside C1 (4) were demonstrated. These sarasinosides characteristically contain one mole each of N-acetylglucosamine and N-acetylgalactosamine in their oligosaccharide moieties.
- Kobayashi,Okamoto,Kitagawa
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p. 2867 - 2877
(2007/10/02)
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- REDUCTIVE ONE-STEP ELIMINATION OF AN ACETOXYL RESIDUE AT β-POSITION OF A NITRO GROUP: SYNTHESES OF (-)-SHIKIMIC ACID FROM D-MANNOSE AND 2-DEOXYSTREPTAMINE PENTAACETATE FROM N-ACETYL-D-GLUCOSAMINE
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By utilizing a reductive one-step elimination reaction of an acetoxyl residue at β-position of the nitro group in cyclitols, a synthesis of the ketocyclitol triacetate (15a), which was already converted to (-)-shikimic acid (16) and (-)-guinic acid (17), from D-mannose (4) and a conversion from N-acetyl-D-glucosamine (18) to 2-deoxystreptamine pentaacetate (22) have been accomplished.
- Yoshikawa, Masayuki,Ikeda, Yoshiharu,Kayakiri, Hiroshi,Kitagawa, Isao
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p. 209 - 214
(2007/10/02)
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- Synthesis and biological activity of some 1-N-substituted 2-acetamido-2-deoxy-beta-D-glycopyranosylamine derivatives and related analogs.
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Several 1-N-substituted derivative [haloacetyl-, glycyl-, (dimethyl)amino-acetyl-, azidoacetyl-, trifluoroacetyl-, and trifluoromethylsulfonyl-] of 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-beta-D-glucopyranosylamine (1) were synthesized as potential metabolic inhibitors of cellular-membrane glycoconjugates. Several fully acetylated derivatives were found to inhibit growth of mouse mammary adenocarcinoma TA3, leukemia L1210, or leukemia P-288 cells at 1-0.01 mM concentration in vitro. Some of these derivatives were less active after O-deacetylation. Analogs of 1 in which NH2-1 was replaced by OH- or OAc-1 were also active on the same cell systems. The growth-inhibitory activity was correlated with inhibition of the incorporation of 2-amino-deoxy-D-glucose and L-leucine into a macromolecular fraction.
- Paul,Bernacki,Korytnyk
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