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51.
Nicolai V. Bovin Elena Yu. Korchagina Tatyana V. Zemlyanukhina Nargiz E. Byramova Oksana E. Galanina Alexandr E. Zemlyakov Alexandr E. Ivanov Vitaly P. Zubov Larisa V. Mochalova 《Glycoconjugate journal》1993,10(2):142-151
Several types of polymeric glycoconjugates,N-substituted polyacrylamides, have been synthesized by the reaction of activated polymers with -aminoalkylglycosides: (i) (carbohydrate-spacer)
n
-polyacrylamide, pseudopolysaccharides; (ii) (carbohydrate-spacer)
n
-phosphatidylethanolamine
m
-polyacrylamide, neoglycolipids, derivatives of phosphatidylethanolamine; (iii) (carbohydrate-spacer)
n
-biotin
m
-polyacrylamide, biotinylated probes; (iv) (carbohydrate-spacer)
n
-polyacrylamide-(macroporous glass), affinity sorbents based on macroporous glass, covalently coated with polyacrylamide. An almost quantitative yield in the conjugation reaction makes it possible to insert in the conjugate a predetermined quantity of the ligand(s).Pseudopolysaccharides proved to be a suitable form of antigen for activation of polystyrene and poly(vinyl chloride) plates (ELISA) and nitrocellulose membranes (dot blot), being advantageous over traditional neoglycoproteins. Polyvalent glycolipids insert well in biological membranes: their physical properties, particularly solubility, can be changed in a desired direction. Biotinylated derivatives were used as probes for detection and analysis of lectins.Abbreviations sp
spacer arm
- PAA
polyacrylamide
- PE
phosphatidylethanolamine
- Biot
biotin
- MPGlass
macroporous glass 200 Å
- ELISA
enzyme-linked immunosorbent assay
- HPLC
high-performance liquid chromatography
- AIBN
azodiisobutyronitrile
- BSA
bovine serum albumin
- DMG
3,6-di-O-methyl-d-glucose
- TLC
thin-layer chromatography
- DMF
dimethylformamide
- DMSO
dimethylsulfoxide
- RI
refractive index
- PBS
phosphate buffered saline (0.14m NaCl, 0.01m sodium phosphate, pH 7.3) 相似文献
52.
S. D. Shiyan V. S. Zueva V. V. Nasonov L. S. Zhigis N. C. Coi N. V. Bovin 《Russian Journal of Bioorganic Chemistry》2004,30(4):358-366
2,3-Sialylation of the lactosamine type N-glycans with trans-sialidase from Trypanosoma
cruzi is reported. Trans-sialidase (160 kDa, pI 5.35–5.65) and its catalytic fragment (70 kDa, pI 6.0–6.3) were isolated from T. ruzi cells and immobilized on ConA-Sepharose. The resulting preparation retained its activity for several months and was repeatedly used for obtaining mono-, di-, tri-, and tetrasialylated 7-amino-4-metylcoumarin-labeled oligosaccharides with various numbers of antennas and for 2,3-sialylation of glycans within glycoproteins and neoglycoconjugates. 相似文献
53.
Rieben R Bovin NV Korchagina EY Oriol R Nifant'ev NE Tsvetkov DE Daha MR Mohacsi PJ Joziasse DH 《Glycobiology》2000,10(2):141-148
Pig-to-human xenotransplantation might be an option to overcome the increasing shortage of human donor organs. However, naturally occurring antibodies in human blood against the Galalpha1-->3Gal antigen on pig endothelial cells lead to hyperacute or, if prevented, acute or delayed vascular rejection of the pig graft. The purpose of this study was therefore to evaluate synthetic oligosaccharides with terminal Galalpha1-->3Gal to inhibit antigen-binding and cytotoxicity of anti-alphaGal antibodies against pig cells. Different oligosaccharides were synthesized chemically and by a combined chemico-enzymatic approach. These included monomeric di-, tri-, and pentasaccharides, a polyacrylamide-conjugate (PAA-Bdi), as well as di-, tetra-, and octamers of Galalpha1-->3Gal. All were tested for inhibitory activity by anti-alphaGal ELISA and complement-dependent cytotoxicity tests. PAA-Bdi was the best inhibitor of binding as well as cytotoxicity of anti-alphaGal antibodies. Monomeric oligosaccharides efficiently prevented binding of anti-alphaGal IgG, but less well that of anti-alphaGal IgM, with tri- and pentasaccharides showing a better efficacy than the disaccharide. The two trisaccharides Galalpha1-->3Galbeta1-->4GlcNAc and Galalpha1-->3Galbeta1-->3GlcNAc were equally effective. Oligomers of Galalpha1-->3Gal were more effective than monomers in blocking the binding of anti-alphaGal IgG. However, they could not block IgM binding, nor could they match the efficacy of PAA-Bdi. We conclude that oligosaccharides with terminal Galalpha1-->3Gal, most effectively as PAA-conjugates, can prevent binding and cytotoxicity of human anti-alphaGal in vitro. The PAA-Bdi conjugate might be most suited for use as a Sepharose-bound immunoabsorption material. 相似文献
54.
Dyukova VI Dementieva EI Zubtsov DA Galanina OE Bovin NV Rubina AY 《Analytical biochemistry》2005,347(1):94-105
The technology of hydrogel microchips manufacturing, which was developed previously for covalent immobilization of DNA and proteins, was applied for the preparation of glycochips and combined glyco/protein chips. Microchips consist of hydrogel drops separated with hydrophobic surface. Spacered amino-saccharides and polyacrylamide glycoconjugates were used for immobilization. Gel elements were approximately 1 nl in volume (150 microm in diameter and 25 microm in height), and the amount of covalently immobilized saccharide in the glycoarray was 0.4-1.7 pmol per gel element. Hydrogel glycan microchips were used for quantitative assay of antibodies against blood group antigens and assay of lectins with fluorescent detection. In all cases, only specific interaction with chip-immobilized saccharides was observed, whereas the background signal was very low. The detection limit of on-chip assays was comparable to that of the standard 96-well plate assays. Mixing of reaction solution allowed us to decrease the duration of the assays significantly: 2-3 h for incubation and development steps and 10 min for washing. A method for determination of association constants for binding of compounds with chip-immobilized ligands from the kinetics of their binding is proposed. Combined microchips containing different types of biomolecules can be designed and used for simultaneous detection of different compounds. 相似文献
55.
Plzák J Holíková Z Dvoránková B Smetana K Betka J Hercogová J Saeland S Bovin NV Gabius HJ 《The Histochemical journal》2002,34(5):247-253
Tandem-repeat C-type lectins (pattern-recognition receptors) with specificity for mannosides are intimately involved in antigen recognition, uptake, routing and presentation in macrophages and dendritic cells. In Langerhans cells, Langerin (CD207), a type-II transmembrane protein with a single C-type carbohydrate recognition domain attached to a heptad repeat in the neck region, which is likely to establish oligomers with an -coiled-coil stalk, has been implicated in endocytosis and the formation of Birbeck granules. The structure of Langerin harbours essential motifs for Ca2+-binding and sugar accommodation. Lectin activity has previously been inferred by diminished antibody binding to cells in the presence of the glycan ligand mannan. In view of the complexity of the C-type lectin/lectin-like network, it is unclear what role Langerin plays for Langerhans cells in binding mannosides. In order to reveal in frozen tissue sections to what extent mannose-binding activity co-localizes with Langerin, we have used a synthetic marker, i.e. a neoglycoprotein carrying mannose maxiclusters, as a histochemical ligand, and computer-assisted fluorescence monitoring in a double-labelling procedure. Mannoside-binding capacity was detected in normal epithelial cells. Double labelling ensured the unambiguous assessment of the binding of the neoglycoprotein in Langerhans cells. Light-microscopically, its localization profile resembled the pattern of immunohistochemical detection of Langerin. This result has implications for suggesting rigorous controls in histochemical analysis of this cell type, because binding of kit reagents, i.e. mannose-rich glycoproteins horseradish peroxidase or avidin, to Langerin (or a spatially closely associated lectin) could yield false-positive signals. To show that recognition of carbohydrate ligands in dendritic cells is not restricted to mannose clusters, we have also documented binding of carrier-immobilized histo-blood group A trisaccharide, a ligand of galectin-3, which was not affected by the presence of a blocking antibody to Langerin. Remarkably, access to the carbohydrate recognition domain of Langerin appeared to be impaired in proliferatively active environments (malignancies, hair follicles), indicating presence of an endogenous ligand with high affinity to saturate the C-type lectin under these conditions. 相似文献
56.
Human plasma trans-sialidase donor and acceptor specificity 总被引:1,自引:0,他引:1
Tertov VV Nikonova EY Nifant'ev NE Bovin NV Orekhov AN 《Biochemistry. Biokhimii?a》2002,67(8):908-913
Earlier we have isolated from human plasma desialylated low density lipoproteins (dLDL) and showed that, first, dLDL induce cholesterol esters accumulation—the main process accompanying atherosclerosis development. Second, the process of lipoprotein desialylation took place in plasma, and, finally, sialic acids removed from LDL are transferred to other serum glycoconjugates. In this study we have isolated from human plasma an enzyme transferring sialic acid residues (trans-sialidase) by affinity chromatography and studied its donor and acceptor specificity. Isolated enzyme in the presence of saccharide acceptor can remove sialic acids from different lipoproteins, glycoproteins (fetuin, transferrin), and gangliosides (GM3, GD3, GM1, GD1a, GD1b). Plasma enzyme translocates 2-6, 2-3 and to a lower extent 2-8 bonded sialic acids. Sialoglycoconjugates of human serum erythrocytes, serum lipoproteins, glycoproteins, and gangliosides can serve as donors of sialic acid for trans-sialidase. Desialylated lipoproteins, especially dLDL,are more preferable sialic acid acceptors. Transferred sialic acid is found to be 2-6, 2-3,and 2-8 connected. 相似文献
57.
L. A. Simeoni N. E. Byramova N. V. Bovin 《Russian Journal of Bioorganic Chemistry》2000,26(3):183-191
The first synthesis of the Neu5Gc analogue of SiaT
n
disaccharide, which can be detected in breast tumors by immunochemical methods, is reported. The regioselective sialylation
of (3-trifluoroacetamidopropyl)-2-azido-2-deoxy-α-D-galactopyranoside with peracetate of the methyl ester ofN-acetoxyacetyl-neuraminic acid β-ethylthioglycoside in the presence ofN-iodosuccinimide and trifluoromethanesulfonic acid (or its trimethylsilyl ester) resulted in the derivatives of α- and β-sialyl(2→6)galactosaminide
in 39 and 32% yields, respectively. The catalytic hydrogenolysis of the azido group and subsequentN- andO-acetylation of the α-anomer gave the peracetate of trifluoroacetamidopropyl glycoside. Removal of the protective groups led
to glycoside Neu5Gcα2→6GalNAcα-O(CH2)3NH2. Using the Neu5Gc derivative with acetoxyacetyl groups at positions O9 and O4 as a donor increases the α-selectivity of sialylation
to afford the α- and β-anomers in 69 and 8% yields, respectively. 相似文献
58.
59.
Chernyy ES Rapoport EM André S Kaltner H Gabius HJ Bovin NV 《Biochemistry. Biokhimii?a》2011,76(8):958-967
Influenza virus is known to bind sialoglycans located on the surface of the host cell. In addition, recent data suggest the
involvement of other molecular targets in viral reception. Of note, a high density of terminal galactose residues is created
on the surface of virions because of the influenza virus’ own neuraminidase activity. Thus, we suggested the possibility for
an interaction of the influenza virus with galactose-binding proteins — galectins. In the present work we studied the influence
of several galectins on the adhesion and further internalization of virus into the cell; six virus strains and three cell
lines were studied. Chicken galectins CG-1A and -2 as well as human galectins HGal-1 and -8 promote virus binding in dose
dependent manner, but they do not influence the internalization stage. Also, galectins are able to restore the ability of
influenza virus to infect desialylated cells up to the level of native cells. When CG-1A in physiological concentrations was
loaded onto viruses, the adhesion level was higher than in the case of on-cell loading. The effect of adhesion increase depends
on the glycan structure of target-cell as well as of virus. The aggregated data suggest a promotional effect of galectins
during the stage of influenza virus binding with the surface of target-cell. 相似文献
60.
Pochechueva T Jacob F Goldstein DR Huflejt ME Chinarev A Caduff R Fink D Hacker N Bovin NV Heinzelmann-Schwarz V 《Glycoconjugate journal》2011,28(8-9):507-517
Anti-glycan antibodies represent a vast and yet insufficiently investigated subpopulation of naturally occurring and adaptive antibodies in humans. Recently, a variety of glycan-based microarrays emerged, allowing high-throughput profiling of a large repertoire of antibodies. As there are no direct approaches for comparison and evaluation of multi-glycan assays we compared three glycan-based immunoassays, namely printed glycan array (PGA), fluorescent microsphere-based suspension array (SA) and ELISA for their efficacy and selectivity in profiling anti-glycan antibodies in a cohort of 48 patients with and without ovarian cancer. The ABO blood group glycan antigens were selected as well recognized ligands for sensitivity and specificity assessments. As another ligand we selected P(1), a member of the P blood group system recently identified by PGA as a potential ovarian cancer biomarker. All three glyco-immunoassays reflected the known ABO blood groups with high performance. In contrast, anti-P(1) antibody binding profiles displayed much lower concordance. Whilst anti-P(1) antibody levels between benign controls and ovarian cancer patients were significantly discriminated using PGA (p=0.004), we got only similar results using SA (p=0.03) but not for ELISA. Our findings demonstrate that whilst assays were largely positively correlated, each presents unique characteristic features and should be validated by an independent patient cohort rather than another array technique. The variety between methods presumably reflects the differences in glycan presentation and the antigen/antibody ratio, assay conditions and detection technique. This indicates that the glycan-antibody interaction of interest has to guide the assay selection. 相似文献