- Hydrogel behavior of a sugar-based gelator by introduction of an unsaturated moiety as a hydrophobic group
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The new sugar-based gelators 1 and 2 were synthesized, and their gelation abilities were evaluated in organic solvents and in water. Compound 1 gelates both water and organic solvents whereas 2 gelates only organic solvents. Superstructural difference between hydrogel 1 and organogel 2 was investigated by CD, TEM, AFM, 1H NMR and XRD. Hydrogel 1 displays a well-developed helical ribbon structure with 20-150 nm diameter and a length of several hundred m whereas organogel 2 shows a twisted fiber structure of diameter 20 nm. CD measurements of hydrogel 1 and organogel 2 indicate that hydrogel 1 maintains a well-ordered chiral structure whereas organogel 2 maintains a relatively disordered chiral structure. The 1H NMR and XRD results suggest that the hydrophobic interaction in hydrogel 1 are relatively weak, with a relatively small region interdigitated between lipophilic alkyl groups. In addition, upon irradiation at 254 nm wavelength, hydrogel 1 reveals a red coloration at 540 nm. These results indicate that the self-assembled hydrogel 1 was polymerized by UV-irradiation. The intensity of the CD spectrum of the polymerized hydrogel markedly decreased. This result indicates that upon polymerization the highly ordered chiral structure of hydrogel 1 changes to a disordered molecular packing structure. The Royal Society of Chemistry 2006.
- Jung, Jong Hwa,Rim, Jeong Ah,Han, Won Seok,Lee, Soo Jin,Lee, Young Joo,Cho, Eun Jin,Kim, Jong Seung,Ji, Qingmin,Shimizu, Toshimi
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Read Online
- Nitrogen-containing aromatic ring derivative containing galactose and application thereof
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The invention belongs to the technical field of medicines, and relates to a nitrogen-containing aromatic ring derivative containing galactose, application thereof and a pharmaceutical composition containing the compound. The invention also relates to a method for preparing the compound and the pharmaceutical composition, and application of the compound and the pharmaceutical composition in prevention or treatment of tumors, inflammatory diseases, autoimmune diseases and other diseases, especially tumors.
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- Glucose-containing nitrogen-containing aromatic ring derivative and application thereof
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The invention belongs to the technical field of medicines, and relates to a glucose-containing nitrogen-containing aromatic ring derivative and application thereof, and a pharmaceutical composition containing the compound. The invention also relates to a
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- Functionalised bicyclic tetramates derived from cysteine as antibacterial agents
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Routes to bicyclic tetramates derived from cysteine permitting ready incorporation of functionality at two different points around the periphery of a heterocyclic skeleton are reported. This has enabled the identification of systems active against Gram-positive bacteria, some of which show gyrase and RNA polymerase inhibitory activity. In particular, tetramates substituted with glycosyl side chains, chosen to impart polarity and aqueous solubility, show high antibacterial activity coupled with modest gyrase/polymerase activity in two cases. An analysis of physicochemical properties indicates that the antibacterially active tetramates generally occupy physicochemical space with MW of 300-600, clog D7.4 of -2.5 to 4 and rel. PSA of 11-22%. This work demonstrates that biologically active 3D libraries are readily available by manipulation of a tetramate skeleton.
- Panduwawala, Tharindi D.,Iqbal, Sarosh,Thompson, Amber L.,Genov, Miroslav,Pretsch, Alexander,Pretsch, Dagmar,Liu, Shuang,Ebright, Richard H.,Howells, Alison,Maxwell, Anthony,Moloney, Mark G.
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supporting information
p. 5615 - 5632
(2019/06/13)
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- Development of Pseudomonas aeruginosa Lectin LecA Inhibitor by using Bivalent Galactosides Supported on Polyproline Peptide Scaffolds
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LecA is a galactose-binding tetrameric lectin from Pseudomonas aeruginosa involved in infection and biofilm formation. The emergent antibiotic resistance of P. aeruginosa has made LecA a promising pharmaceutical target to treat such infections. To develop LecA inhibitors, we exploit the unique helical structure of polyproline peptides to create a scaffold that controls the galactoside positions to fit their binding sites on LecA. With a modular scaffold design, both the galactoside ligands and the inter-ligand distance can be altered conveniently. We prepared scaffolds with spacings of 9, 18, 27, and 36 ? for ligand conjugation and found that glycopeptides with galactosides ligands three helical turns (27 ?) apart best fit LecA. In addition, we tested different galactose derivatives on the selected scaffold (27 ?) to improve the binding avidity to LecA. The results validate a new multivalent scaffold design and provide useful information for LecA inhibitor development.
- Huang, Shao-Feng,Lin, Cin-Hao,Lai, Yu-Tsung,Tsai, Chia-Lung,Cheng, Ting-Jen R.,Wang, Sheng-Kai
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p. 686 - 700
(2018/03/05)
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- Preparation method of galactose-containing fatty acid derivative and application of preparation method in field of medicine
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The invention relates to a novel p-fatty alkylamide phenyl-beta-D-galactoside compound, a preparation method and application, belonging to the technical field of medicine. A structure general formula of the compound is shown in the description, wherein R is selected from (CH2)6CH3, (CH2)10CH3, (CH2)12CH3, (CH2)14CH3, and (CH2)7CH=CH (CH2)7CH3. The compound has stronger inhibitory activity to tumor cells, and can be used for tumor therapies.
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Paragraph 0023; 0024; 0044; 0045
(2016/12/01)
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- Glycosylated lanthanide cyclen complexes as luminescent probes for monitoring glycosidase enzyme activity
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The development of synthetic chemical probes for the detection of enzymes is extremely important for biological, medicinal, and industrial applications. Here we report the synthesis of an array of novel glycosylated Tb(iii) complexes, their photophysical properties in solution, and their ability to function as luminescent probes for observing glycosidase enzyme activity in real time. Our initial studies into the application of these complexes for the detection of the Concanavalin A (ConA) lectin is also reported, highlighting the broad scope of these novel chemical probes.
- Burke, Helen M.,Gunnlaugsson, Thorfinnur,Scanlan, Eoin M.
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p. 9133 - 9145
(2016/10/07)
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- Development and optimization of a competitive binding assay for the galactophilic low affinity lectin LecA from: Pseudomonas aeruginosa
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Infections with the Gram-negative bacterium Pseudomonas aeruginosa result in a high mortality among immunocompromised patients and those with cystic fibrosis. The pathogen can switch from planktonic life to biofilms, and thereby shields itself against antibiotic treatment and host immune defense to establish chronic infections. The bacterial protein LecA, a C-type lectin, is a virulence factor and an integral component for biofilm formation. Inhibition of LecA with its carbohydrate ligands results in reduced biofilm mass, a potential Achilles heel for treatment. Here, we report the development and optimization of a fluorescence polarization-based competitive binding assay with LecA for application in screening of potential inhibitors. As a consequence of the low affinity of d-galactose for LecA, the fluorescent ligand was optimized to reduce protein consumption in the assay. The assay was validated using a set of known inhibitors of LecA and IC50 values in good agreement with the known Kd values were obtained. Finally, we employed the optimized assay to screen sets of synthetic thio-galactosides and natural blood group antigens and report their structure-activity relationship. In addition, we evaluated a multivalent fluorescent assay probe for LecA and report its applicability in an inhibition assay.
- Joachim, Ines,Rikker, Sebastian,Hauck, Dirk,Ponader, Daniela,Boden, Sophia,Sommer, Roman,Hartmann, Laura,Titz, Alexander
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p. 7933 - 7948
(2016/08/30)
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- Synthetic multivalent ligands for cholera & cholera-like toxins: Protected cyclic neoglycopeptides
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Synthesis of a set of novel glycopeptide analogues as potential cholera/cholera-like toxin inhibitors in their protected form is described. They include di-, tri-, tetra- and pentavalent scaffolds. The synthetic steps were achieved using a combination of solvent-free mechanochemical as well as the conventional solution-phase reactions. During the conventional DIC-HOBt-mediated peptide coupling followed for the preparation of certain glycopeptide analogues an interesting in situ Fmoc deprotection was observed which has been demonstrated to hold potential for synthesiszing glycopeptides/neoglycopeptides with extended polyamide chains.
- Kumar, Vajinder,Yadav, Narender,Kartha, K.P. Ravindranathan
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- Glucose fatty acid-containing derivative preparation method and application of derivative in medical field
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The invention relates to a novel p-fatty alkyl amidophenyl-beta-D-glucoside compound and a preparation method and an application thereof, which belong to the technical field of medicine. According to the invention, a structural general formula is shown as
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Paragraph 0047; 0048
(2016/10/10)
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- Synthesis and inhibitory activity evaluation of 2,6-disubstituted purine derivatives
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A series of novel 2,6-disubstituted purine derivatives were designed and synthesized from 2,6-dichloropurine. The structures of target compounds were determined by 1H-NMR, 13C-NMR, and HRMS. The synthesized compounds were evaluated for their inhibitory activities against lung cancer cell lines of A549 and liver cancer cell lines of Bel-7402. 2-(4-Benzyloxy-phenylamino)-6-(cyclohexylamino)purine(3), 2-(4-chloro-phenylamino)-6-(n-butylamino)purine (5), 2-(4-morpholinoamino)-6-(4-hydroxy-phenylamino)purine (9), and 2-(4-O-galactosyl-phenylamino)-6-(cyclohexylamino)purine (12) exhibited moderate inhibitory activity.
- Liu, Hongxia,Li, Libo,Qurat-Ul-Ain, Shaikh,Jiang, Tao
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p. 473 - 477
(2015/03/30)
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- Synthesis of cross-linked glycopeptides and ureas by a mechanochemical, solvent-free reaction and determination of their structural properties by TEM and X-ray crystallography
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A highly efficient and cost-effective green method for the synthesis of complex glycopeptides and ureas mediated by carbonyl diimidazole under solvent-free conditions is reported. The reactions could be performed conveniently in a planetary ball mill by dry grinding, and the isolation of the novel sugar derivatives thus produced could be very efficiently achieved by size exclusion chromatography with environmentally benign substances. A diacetone galactose based diamide, upon crystallization, could be examined by X-ray crystallography and was found to possess a heart-shaped structure. Although the 4-aminophenyl galactoside based diamide synthesized formed spherical particles, the alanine-based diamide formed nanofilamentous/-tubular structures as analyzed by TEM imaging.
- Kumar, Vajinder,Giri, Santosh Kumar,Venugopalan, Paloth,Kartha, K.P. Ravindranathan
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p. 1605 - 1613
(2015/02/02)
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- Synthesis of galactoclusters by metal-free thiol "click chemistry" and their binding affinities for pseudomonas aeruginosa lectin leca
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Mannose-centered galactoclusters specific for lectin I of Pseudomonas aeruginosa (LecA) were synthesised by a combination of phosphoramidite chemistry and metal-free thiol click chemistry (i.e., thiol addition to acrylamide or nucleophilic displacement of
- Ligeour, Caroline,Dupin, Lucie,Marra, Alberto,Vergoten, Gérard,Meyer, Albert,Dondoni, Alessandro,Souteyrand, Eliane,Vasseur, Jean-Jacques,Chevolot, Yann,Morvan, Fran?ois
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p. 7621 - 7630
(2015/04/22)
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- Carbohydrate coatings via aryldiazonium chemistry for surface biomimicry
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Carbohydrates are extremely important biomolecules and their immobilization onto solid surfaces is of interest for the development of new biomimetic materials and of new methods for understanding processes in glycobiology. We have developed an efficient surface modification methodology for the functionalization of a range of materials with biologically active carbohydrates based on aryldiazonium chemistry. We describe the synthesis and characterization of carbohydrate reagents, which were subsequently employed for the one-step, solution-based modification of carbon, metals, and alloys with monosaccharides. We used a combination of spectroscopic and nanogravimetric methods to characterize the structure of the carbohydrate layers; we report an average surface coverage of 7.8 × 10-10 mol cm-2 under our experimental conditions. Concanavalin A, a mannose-binding lectin, and Peanut Agglutinin, a galactose-binding lectin, were found to bind from solution to their respective monosaccharide binding partners immobilized at the surface. This result suggests that the spontaneous chemisorption of aryldiazonium monosaccharide precursors leads to the formation of monosaccharide layers that retain the biological recognition specificity of the parent carbohydrate molecule. Finally, we carried out measurements using fluorescently labeled Bovine Serum Albumin (BSA) and found that these carbohydrate coatings reduce unspecific adsorption of this protein at carbon surfaces. These results suggest that aryldiazonium-derived carbohydrate coatings may offer a promising strategy for preventing undesirable protein accumulation onto surfaces.
- Jayasundara, Dilushan R.,Duff, Thomas,Angione, M. Daniela,Bourke, Jean,Murphy, Deirdre M.,Scanlan, Eoin M.,Colavita, Paula E.
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p. 4122 - 4128
(2013/11/19)
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- Glycosylated tris-bipyridine ferrous complexes to provide dynamic combinatorial libraries for probing carbohydrate-carbohydrate interactions
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2,2-Bipyridines having β-lactoside, β-d-glucoside, β-d-galactoside, and N-acetyl-β-d-glucosaminide were prepared and then, complexed with ferrous ion to afford trivalent glycoclusters having tris-bipyridine ferrous complex cores. Each glycocluster provides a dynamic combinatorial library composed of four diastereomeric stereoisomers (Δmer, Δfac, Λmer, and Λfac) whose ratios depend on their relative stabilities. CD spectral analyses of these glycoclusters showed that various cations (Na+, Mg2+, K+ or Ca2+) enriched Δ-forms of the glycocluster having β-lactosides and N-acetyl-β-d-glucosaminides possibly by cations-induced intramolecular carbohydrate-carbohydrate interactions.
- Nakamura, Motomi,Tsutsumi, Mayuka,Ishikawa, Yoshiaki,Umemiya, Haruka,Izawa, Kazumi,Abe, Haruka,Togashi, Yosuke,Kinone, Tatsuya,Sekiguchi, Sho,Igumi, Mihiro,Ide, Kanako,Hasegawa, Teruaki,Hasegawa, Toki
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supporting information
p. 3019 - 3026
(2013/03/29)
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- GLYCOMIMETIC COMPOUNDS AS ANTI-INFECTIOUS AGAINST PATHOGENS LECTINS
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The present invention relates to a calixarene-based glycosylated compound (I) having the formula: (I) wherein D is independently selected in the group comprising a —CH2-group, an oxygen atom, a sulphur atom, a sulfinyl group or a sulfonyl group, E is independently selected in the group comprising a hydrogen, an alkyl having from 1 to 10 carbon atoms, an aryl having from 6 to 20 carbon atoms, a nitrogen dioxide group, an azide group, an amino group, a guanidinium group, a halogen atom, a —CH2R group wherein R is a hydroxyl, a halogen, an amino group, a N(alkyl)2 group, a NH(alkyl) group, or E represents a —CO—R′ wherein R′ is a hydrogen atom, a hydroxyl group or an amino, B represents a A-C group wherein A is independently selected in the group comprising an oxygen atom, a sulfur atom, a NH group or a (CH2)i group, i being an integer from 1 to 10, C is independently selected in the group comprising a hydrogen, an alkyl, an alkenyl, an alkynyl, or C is a group of formula (II). The present invention also relates to a pharmaceutical composition characterized in that it comprises the said calixarene-based glycosylated compound (I), in combination with pharmaceutically acceptable carriers or diluents. The present invention also relates to the use of the said calixarene-based glycosylated compound (I) or the said pharmaceutical composition, for the manufacture of a drug intended to prevent or treat bacterial infections from pathogens that use lectins in the first steps of infection.
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Paragraph 0159-0161
(2013/10/07)
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- GLYCOMIMETIC COMPOUNDS AS ANTI-INFECTIOUS AGAINST PATHOGENS LECTINS
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The present invention relates to a calixarene-based glycosylated compound (I) having the formula : (I) wherein D is independently selected in the group comprising a –CH2 –group, an oxygen atom, a sulphur atom, a sulfinyl group or a sulfonyl group, E is independently selected in the group comprising a hydrogen, an alkyl having from 1 to 10 carbon atoms, an aryl having from 6 to 20 carbon atoms, a nitrogen dioxide group, an azide group, an amino group, a guanidinium group,a halogen atom, a –CH2 R group wherein R is a hydroxyl, a halogen, an amino group, a N(alkyl)2 group, a NH(alkyl) group, or E represents a –CO-R' wherein R' is a hydrogen atom, a hydroxyl group or an amino, B represents a A–C group wherein A is independently selected in the group comprising an oxygen atom, a sulfur atom, a NH group or a (CH2 )i group, i being an integer from 1 to 10, C is independently selected in the group comprising a hydrogen, an alkyl, an alkenyl, an alkynyl, or C is a group of formula (II). The present invention also relates to a pharmaceutical composition characterized in that it comprises the said calixarene-based glycosylated compound (I), in combination with pharmaceutically acceptable carriers or diluents. The present invention also relates to the use of the said calixarene-based glycosylated compound (I) or the said pharmaceutical composition, for the manufacture of a drug intended to prevent or treat bacterial infections from pathogens that use lectins in the first steps of infection.
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Page/Page column 23
(2012/06/30)
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- Rational design and synthesis of optimized glycoclusters for multivalent lectin-carbohydrate interactions: Influence of the linker arm
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The design of multivalent glycoclusters requires the conjugation of biologically relevant carbohydrate epitopes functionalized with linker arms to multivalent core scaffolds. The multigram-scale syntheses of three structurally modified triethyleneglycol analogues that incorporate amide moiety(ies) and/or a phenyl ring offer convenient access to a series of carbohydrate probes with different water solubilities and rigidities. Evaluation of flexibility and determination of preferred conformations were performed by conformational analysis. Conjugation of the azido-functionalized carbohydrates with tetra-propargylated core scaffolds afforded a library of 18 tetravalent glycoclusters, in high yields, by CuI-catalyzed azide-alkyne cycloaddition (CuAAC). The compounds were evaluated for their ability to bind to PA-IL (the LecA lectin from the opportunistic pathogen Pseudomonas aeruginosa). Biochemical evaluation through inhibition of hemagglutination assays (HIA), enzyme-linked lectin assays (ELLA), surface plasmon resonance (SPR), and isothermal titration microcalorimetry (ITC) revealed improved and unprecedented affinities for one of the monovalent probes (Kd=5.8 μM) and also for a number of the tetravalent compounds that provide several new nanomolar ligands for this tetrameric lectin. Copyright
- Cecioni, Samy,Praly, Jean-Pierre,Matthews, Susan E.,Wimmerova, Michaela,Imberty, Anne,Vidal, Sebastien
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supporting information; experimental part
p. 6250 - 6263
(2012/07/03)
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- Selective α-glucosidase substrates and inhibitors containing short aromatic peptidyl moieties
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We constructed a library of sugar-dipeptide conjugate to find out the best complementary against hydrophobic pocket of α-glucosidase. The best substrate showed 150-fold improved Km value relative p-acetaminophenyl-α-d-glucopyranoside for α-glucosidase from Bacillus stearothermophillus. Using information from the complementary, we synthesized sp-WY and β-Glc-sp-WY, which selectivity inhibited the cognate enzyme.
- Park, Sangeun,Hyun, Soonsil,Yu, Jaehoon
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supporting information; experimental part
p. 2441 - 2444
(2011/06/17)
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- N-Arylimidazole synthesis by cross-cycloaddition of isocyanides using a novel catalytic system
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A direct catalytic synthesis of N-arylimidazoles starting from the corresponding N-arylformamides and N-formylglycine esters is?described. Application to different aryl substituted electron-withdrawing and -donating groups provided the analogous heterocyc
- Bonin, Marc-André,Giguère, Denis,Roy, René
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p. 4912 - 4917
(2008/02/01)
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- Stabilization of an asymmetric bolaamphiphilic sugar-based crown ether hydrogel by hydrogen bonding interaction and its sol-gel transcription
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Asymmetric bolaamphiphilic sugar-based hydrogelators (1-3) were synthesized and their gelation ability with and without alkylammonium ions was investigated by CD, TEM, FTIR and NMR. These compounds acted as versatile gelators for organic solvents and wate
- Jung, Jong Hwa,Rim, Jeong Ah,Cho, Eun Jin,Lee, Soo Jin,Jeong, Il Yun,Kameda, Naohiro,Masuda, Mitsutoshi,Shimizu, Toshimi
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p. 7449 - 7456
(2008/02/05)
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- Sol-Gel Polycondensation of Tetraethyl Orthosilicate (TEOS) in Sugar-Based Porphyrin Organogels: Inorganic Conversion of a Sugar-Directed Porphyrinic Fiber Library through Sol-Gel Transcription Processes
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Sugar-appended porphyrins (1a-e) with monosaccharide groups at their periphery have been rationally designed for a new class of gelating reagents. A few of these compounds have the tendancy to form one-dimensional aggregates stable enough to show successful gelation ability for DMF-alcohol mixed solvents. The aggregation mode in the specific columnar super structures has been evaluated in detail by UV-visible spectrometry (UV/Vis), circular dichroism (CD), scanning electron microscopy (SEM), and transmission electron microscopy (TEM). All UV-visible spectra of sugar-appended porphyrinic gels obtained from la-c exhibit Soret band absorptions, which shift to lower wave-length and are significantly broadened. This phenomenon indicates that these porphyrin cores strongly interact with each other in an H-aggregate fashion, which drives the generation of a one-dimensional porphyrin-stacking array. The CD spectra of the organogels from 1a and 1b, which are in anomers, exhibit an almost symmetric pattern, whereas the gel from 1c gives a completely different pattern. This implies that the gel fibrils wind themselves in a right- or left-handed fashion; this reflects chirality in the specific molecular structure of the gelators. The results from SEM for the gel fibrils are in good agreement with the CD patterns. The gel fibrils in la possess left-handed helicity, whereas those in lb wind themselves right-handedly. Macroscopic helical morphology reflects the microscopic structure well at a molecular level, which gives structural variety of the gel fibrils, which can be defined by the sugar library. Inorganic conversion of the organic helical fibrils by a sol-gel transcription process successfully gives the helical-silica structures, which finely inherit the organic morphology. A striking observation is that a unimolecular porphyrin-stacking array is also transcribed into silica fibers when the optimized sol-gel reaction conditions are selected. A sugar-based organic-fiber library in porphyrinic gels thus provides a variety of inorganic materials through the sol-gel transcription process.
- Kawano, Shin-Ichiro,Tamaru, Shun-Ichi,Fujita, Norifumi,Shinkai, Seiji
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p. 343 - 351
(2007/10/03)
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- Resolution of enantiomers using sugar-carrying polyisocyanides as chiral stationary phases for HPLC
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3,5-Dimethylphenylcarbamate derivatives of α/β-glucose and α/β-galactose-carrying helical poly(phenyl isocyanide)s were used as chiral stationary phases (CSPs) for HPLC to estimate their chiral recognition abilities. CD spectroscopy suggested that the hel
- Tsuchida, Akiko,Hasegawa, Teruaki,Kobayashi, Kazukiyo,Yamamoto, Chiyo,Okamoto, Yoshio
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p. 2681 - 2685
(2007/10/03)
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- Synthesis and biological activity of glycosyl conjugates of N-(4-hydroxyphenyl)retinamide
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Three glycosyl (glucosyl, galactosyl, mannosyl) conjugates of 4-hydroxyphenylretinamide have been synthesized and tested on a broad variety of tumor cells. All three compounds are active on promyelocytic leukemia cell lines HL60 but less than the parent compound 4-HPR. Among them, the mannosyl analog stands out by its very low toxicity. Copyright
- Winum, Jean-Yves,Leydet, Alain,Seman, Michel,Montero, Jean-Louis
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p. 319 - 324
(2007/10/03)
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- New organogelators bearing both sugar and cholesterol units: An approach toward molecular design of universal gelators
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The gelators of organic solvents are classified into two categories on the basis of their basic intermolecular forces: hydrogen-bonded or nonhydrogen-bonded. To utilize these two interactions cooperatively for organogel formation we newly synthesized seven gelators (1-7) and two reference compounds (8 and 9) which have both a cholesterol moiety and a saccharide moiety within one molecule. The solubility of 1-7 changed drastically from totally insoluble one to very soluble one depending on the saccharide absolute configuration. In general, the gelator became very insoluble when it includes many equatorial OH groups, whereas it became very soluble when it includes many axial OH groups. Gelators 2 and 5 bearing two equatorial OH groups and one axial OH group acted as good gelators and in several cases the sol-gel phase-transition temperatures (measured in a sealed tube) were higher than the boiling points. The SEM observations of the xerogels established that the stable gels contain the entangled fibrous network. These results indicate that a very stable organogel can be designed by a cooperative coagulative effect of a cholesterol-cholesterol interaction and a saccharide-saccharide interaction.
- Amaike,Kobayashi,Shinkai
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p. 2553 - 2558
(2007/10/03)
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- Mitomycin derivatives having reduced bone marrow toxicity, processes for their preparation, and the uses thereof
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The invention relates to certain derivatives of mitomycins A and C and the use thereof to treat bacterial infections and to supress the growth of cancer cells. The invention also relates to processes for the preparation of the mitomycin derivatives of the invention.
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- Syntheses and Transformations of Glycohydrolase Substrates into Protein Conjugates Based on Michael Additions
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The glycosyl chloride 1 and bromides 2 and 3 were stereospecifically transformed into p-nitrophenyl glycosides by phase transfer catalysis; these glycohydrolase substrates were reduced and N-acryloylated to afford Michael acceptors which reacted with amine functions of proteins.
- Roy, Rene,Tropper, Francois D.,Morrison, Tara,Boratynski, Janusz
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p. 536 - 538
(2007/10/02)
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