메뉴 건너뛰기




Volumn 4, Issue 9, 2009, Pages 741-750

Fluorescent glycosylamides produced by microscale derivatization of free glycans for natural glycan microarrays

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLOYL CHLORIDE; ALDEHYDE; AMIDE; CHLORINE DERIVATIVE; FLUORESCENT DYE; GLYCAN; GLYCOSYLAMIDE; MONOSACCHARIDE; UNCLASSIFIED DRUG;

EID: 70349281524     PISSN: 15548929     EISSN: None     Source Type: Journal    
DOI: 10.1021/cb900067h     Document Type: Article
Times cited : (61)

References (49)
  • 2
    • 35548974811 scopus 로고    scopus 로고
    • Paradigms for glycanbinding receptors in cell adhesion
    • Taylor, M. E., and Drickamer, K. (2007) Paradigms for glycanbinding receptors in cell adhesion, Curr. Opin. Cell Biol. 19, 572-577.
    • (2007) Curr. Opin. Cell Biol. , vol.19 , pp. 572-577
    • Taylor, M.E.1    Drickamer, K.2
  • 3
    • 33748195979 scopus 로고    scopus 로고
    • Glycosylation in Cellular Mechanisms of Health and Disease
    • DOI 10.1016/j.cell.2006.08.019, PII S0092867406010865
    • Ohtsubo, K., and Marth, J. D. (2006) Glycosylation in cellular mechanisms of health and disease, Cell 126, 855-867. (Pubitemid 44310784)
    • (2006) Cell , vol.126 , Issue.5 , pp. 855-867
    • Ohtsubo, K.1    Marth, J.D.2
  • 4
    • 0141756182 scopus 로고    scopus 로고
    • Glycan-dependent leukocyte adhesion and recruitment in inflammation
    • DOI 10.1016/j.ceb.2003.08.002
    • Lowe, J. B. (2003) Glycan-dependent leukocyte adhesion and recruitment in inflammation, Curr. Opin. Cell Biol. 15, 531-538. (Pubitemid 37176961)
    • (2003) Current Opinion in Cell Biology , vol.15 , Issue.5 , pp. 531-538
    • Lowe, J.B.1
  • 5
    • 33749071408 scopus 로고    scopus 로고
    • Structural aspects of glycomes with a focus on N-glycosylation and glycoprotein folding
    • Petrescu, A. J., Wormald, M. R., and Dwek, R. A. (2006) Structural aspects of glycomes with a focus on N-glycosylation and glycoprotein folding, Curr. Opin. Struct. Biol. 16, 600-607.
    • (2006) Curr. Opin. Struct. Biol. , vol.16 , pp. 600-607
    • Petrescu, A.J.1    Wormald, M.R.2    Dwek, R.A.3
  • 6
    • 33644830238 scopus 로고    scopus 로고
    • N-linked oligosaccharides as outfitters for glycoprotein folding, form and function
    • DOI 10.1016/j.tibs.2006.01.003, PII S0968000406000247
    • Mitra, N., Sinha, S., Ramya, T. N., and Surolia, A. (2006) N-linked oligosaccharides as outfitters for glycoprotein folding, form and function, Trends Biochem. Sci. 31, 156-163. (Pubitemid 43357996)
    • (2006) Trends in Biochemical Sciences , vol.31 , Issue.3 , pp. 156-163
    • Mitra, N.1    Sinha, S.2    Ramya, T.N.C.3    Surolia, A.4
  • 7
    • 33749183647 scopus 로고    scopus 로고
    • N-Linked glycan recognition and processing: The molecular basis of endoplasmic reticulum quality control
    • Moremen, K. W., and Molinari, M. (2006) N-Linked glycan recognition and processing: the molecular basis of endoplasmic reticulum quality control, Curr. Opin. Struct. Biol. 16, 592-599.
    • (2006) Curr. Opin. Struct. Biol. , vol.16 , pp. 592-599
    • Moremen, K.W.1    Molinari, M.2
  • 8
    • 33751508817 scopus 로고    scopus 로고
    • N-Glycan processing in ER quality control
    • Ruddock, L. W., and Molinari, M. (2006) N-Glycan processing in ER quality control, J. Cell Sci. 119, 4373-4380.
    • (2006) J. Cell Sci. , vol.119 , pp. 4373-4380
    • Ruddock, L.W.1    Molinari, M.2
  • 9
    • 0035054508 scopus 로고    scopus 로고
    • Glycans as legislators of hostmicrobial interactions: Spanning the spectrum from symbiosis to pathogenicity
    • Hooper, L. V., and Gordon, J. I. (2001) Glycans as legislators of hostmicrobial interactions: spanning the spectrum from symbiosis to pathogenicity, Glycobiology 11, 1R-10R.
    • (2001) Glycobiology , vol.11
    • Hooper, L.V.1    Gordon, J.I.2
  • 10
    • 5744226307 scopus 로고    scopus 로고
    • Tools for glycomics: Mapping interactions of carbohydrates in biological systems
    • Ratner, D. M., Adams, E. W., Disney, M. D., and Seeberger, P. H. (2004) Tools for glycomics: mapping interactions of carbohydrates in biological systems, ChemBioChem 5, 1375-1383.
    • (2004) ChemBioChem , vol.5 , pp. 1375-1383
    • Ratner, D.M.1    Adams, E.W.2    Disney, M.D.3    Seeberger, P.H.4
  • 11
    • 45749142499 scopus 로고    scopus 로고
    • Carbohydrate arrays as tools for research and diagnostics
    • Horlacher, T., and Seeberger, P. H. (2008) Carbohydrate arrays as tools for research and diagnostics, Chem. Soc. Rev. 37, 1414-1422.
    • (2008) Chem. Soc. Rev. , vol.37 , pp. 1414-1422
    • Horlacher, T.1    Seeberger, P.H.2
  • 12
    • 52449127409 scopus 로고    scopus 로고
    • Carbohydrate microarrays as powerful tools in studies of carbohydrate-mediated biological processes
    • Park, S., Lee, M. R., and Shin, I. (2008) Carbohydrate microarrays as powerful tools in studies of carbohydrate-mediated biological processes, Chem. Commun. (Cambridge) 4389-4399.
    • (2008) Chem. Commun. (Cambridge) , pp. 4389-4399
    • Park, S.1    Lee, M.R.2    Shin, I.3
  • 13
    • 0020008871 scopus 로고
    • Detection of glycolipid ligands by direct binding of carbohydrate-binding proteins to thin-layer chromatograms
    • Magnani, J. L., Brockhaus, M., Smith, D. F., and Ginsburg, V. (1982) Detection of glycolipid ligands by direct binding of carbohydrate-binding proteins to thin-layer chromatograms, Methods Enzymol. 83, 235-241.
    • (1982) Methods Enzymol. , vol.83 , pp. 235-241
    • Magnani, J.L.1    Brockhaus, M.2    Smith, D.F.3    Ginsburg, V.4
  • 14
    • 33751202735 scopus 로고    scopus 로고
    • Determination of glycolipidprotein interaction specificity
    • Lopez, P. H., and Schnaar, R. L. (2006) Determination of glycolipidprotein interaction specificity, Methods Enzymol. 417, 205-220.
    • (2006) Methods Enzymol. , vol.417 , pp. 205-220
    • Lopez, P.H.1    Schnaar, R.L.2
  • 15
    • 3042786282 scopus 로고    scopus 로고
    • Oligosaccharide microrrays to decipher the glyco code
    • DOI 10.1038/nrm1428
    • Feizi, T., and Chai, W. (2004) Oligosaccharide microarrays to decipher the glyco code, Nat. Rev. Mol. Cell. Biol. 5, 582-588. (Pubitemid 38868587)
    • (2004) Nature Reviews Molecular Cell Biology , vol.5 , Issue.7 , pp. 582-588
    • Feizi, T.1    Chai, W.2
  • 16
    • 0141953233 scopus 로고    scopus 로고
    • Carbohydrate microarrays - A new set of technologies at the frontiers of glycomics
    • DOI 10.1016/j.sbi.2003.09.002
    • Feizi, T., Fazio, F., Chai, W., and Wong, C. H. (2003) Carbohydrate microarrays - a new set of technologies at the frontiers of glycomics, Curr. Opin. Struct. Biol. 13, 637-645. (Pubitemid 37244119)
    • (2003) Current Opinion in Structural Biology , vol.13 , Issue.5 , pp. 637-645
    • Feizi, T.1    Fazio, F.2    Chai, W.3    Wong, C.-H.4
  • 17
    • 33750970829 scopus 로고    scopus 로고
    • Identification of ligand specificities for glycan-binding proteins using glycan arrays
    • Alvarez, R. A., and Blixt, O. (2006) Identification of ligand specificities for glycan-binding proteins using glycan arrays, Methods Enzymol. 415, 292-310.
    • (2006) Methods Enzymol. , vol.415 , pp. 292-310
    • Alvarez, R.A.1    Blixt, O.2
  • 18
    • 0037009016 scopus 로고    scopus 로고
    • Fabrication of carbohydrate chips for studying protein-carbohydrate interactions
    • DOI 10.1002/1521-3773(20020902)41:17<3180::AID-ANIE3180>3.0.CO;2-S
    • Park, S., and Shin, I. (2002) Fabrication of carbohydrate chips for studying protein-carbohydrate interactions, Angew. Chem., Int. Ed. 41, 3180-3182. (Pubitemid 35014379)
    • (2002) Angewandte Chemie - International Edition , vol.41 , Issue.17 , pp. 3180-3182
    • Park, S.1    Shin, I.2
  • 19
    • 3042562999 scopus 로고    scopus 로고
    • Probing protein-carbohydrate interactions with microarrays of synthetic oligosaccharides
    • DOI 10.1002/cbic.200300804
    • Ratner, D. M., Adams, E. W., Su, J., O'Keefe, B. R., Mrksich, M., and Seeberger, P. H. (2004) Probing protein-carbohydrate interactions with microarrays of synthetic oligosaccharides, ChemBioChem 5, 379-382. (Pubitemid 39257133)
    • (2004) ChemBioChem , vol.5 , Issue.3 , pp. 379-382
    • Ratner, D.M.1    Adams, E.W.2    Su, J.3    O'Keefe, B.R.4    Mrksich, M.5    Seeberger, P.H.6
  • 22
    • 35848950757 scopus 로고    scopus 로고
    • General microarray technique for immobilization and screening of natural glycans
    • de Boer, A. R., Hokke, C. H., Deelder, A. M., and Wuhrer, M. (2007) General microarray technique for immobilization and screening of natural glycans, Anal. Chem. 79, 8107-8113.
    • (2007) Anal. Chem. , vol.79 , pp. 8107-8113
    • De Boer, A.R.1    Hokke, C.H.2    Deelder, A.M.3    Wuhrer, M.4
  • 24
    • 58549107432 scopus 로고    scopus 로고
    • Novel fluorescent glycan microarray strategy reveals ligands for galectins
    • Song, X., Xia, B., Stowell, S. R., Lasanajak, Y., Smith, D. F., and Cummings, R. D. (2009) Novel fluorescent glycan microarray strategy reveals ligands for galectins, Chem. Biol. 16, 36-47.
    • (2009) Chem. Biol. , vol.16 , pp. 36-47
    • Song, X.1    Xia, B.2    Stowell, S.R.3    Lasanajak, Y.4    Smith, D.F.5    Cummings, R.D.6
  • 25
    • 33751363180 scopus 로고    scopus 로고
    • Arraying glycomics: A novel bi-functional spacer for one-step microscale derivatization of free reducing glycans
    • DOI 10.1093/glycob/cwl044
    • Bohorov, O., Andersson-Sand, H., Hoffmann, J., and Blixt, O. (2006) Arraying glycomics: a novel bi-functional spacer for one-step microscale derivatization of free reducing glycans, Glycobiology 16, 21C-27C. (Pubitemid 44811580)
    • (2006) Glycobiology , vol.16 , Issue.12
    • Bohorov, O.1    Andersson-Sand, H.2    Hoffmann, J.3    Blixt, O.4
  • 26
    • 0028987976 scopus 로고
    • 1H NMR characterization of a hen ovalbumin tyrosinamide N-linked oligosaccharide library
    • Corradi Da Silva, M. L., Stubbs, H. J., Tamura, T., and Rice, K. G. (1995) 1H NMR characterization of a hen ovalbumin tyrosinamide N-linked oligosaccharide library, Arch. Biochem. Biophys. 318, 465-475.
    • (1995) Arch. Biochem. Biophys. , vol.318 , pp. 465-475
    • Corradi Da Silva, M.L.1    Stubbs, H.J.2    Tamura, T.3    Rice, K.G.4
  • 27
    • 0019877155 scopus 로고
    • The carbohydrate-binding specificity of pea and lentil lectins. Fucose is an important determinant
    • Kornfeld, K., Reitman, M. L., and Kornfeld, R. (1981) The carbohydrate-binding specificity of pea and lentil lectins. Fucose is an important determinant, J. Biol. Chem. 256, 6633-6640.
    • (1981) J. Biol. Chem. , vol.256 , pp. 6633-6640
    • Kornfeld, K.1    Reitman, M.L.2    Kornfeld, R.3
  • 28
    • 0017146754 scopus 로고
    • The structural basis of the different affinities of two types of acidic N-glycosidic glycopeptides for concanavalin A-sepharose
    • Krusius, T., Finne, J., and Rauvala, H. (1976) The structural basis of the different affinities of two types of acidic N-glycosidic glycopeptides for concanavalin A-sepharose, FEBS Lett. 72, 117-120.
    • (1976) FEBS Lett. , vol.72 , pp. 117-120
    • Krusius, T.1    Finne, J.2    Rauvala, H.3
  • 29
    • 0016772320 scopus 로고
    • Fractionation of glycopeptides by affinity column chromatography on concanavalin A-sepharose
    • Ogata, S., Muramatsu, T., and Kobata, A. (1975) Fractionation of glycopeptides by affinity column chromatography on concanavalin A-sepharose, J. Biochem. 78, 687-696.
    • (1975) J. Biochem. , vol.78 , pp. 687-696
    • Ogata, S.1    Muramatsu, T.2    Kobata, A.3
  • 30
    • 0021893594 scopus 로고
    • Fractionation of L-fructose-containing oligosaccharides on immobilized Aleuria aurantia lectin
    • Yamashita, K., Kochibe, N., Ohkura, T., Ueda, I., and Kobata, A. (1985) Fractionation of L-fucose-containing oligosaccharides on immobilized Aleuria aurantia lectin, J. Biol. Chem. 260, 4688-4693. (Pubitemid 15034604)
    • (1985) Journal of Biological Chemistry , vol.260 , Issue.8 , pp. 4688-4693
    • Yamashita, K.1    Kochibe, N.2    Ohkura, T.3
  • 31
    • 0017382345 scopus 로고
    • Carbohydrate binding specificity of four N-acetyl-D-galactosamine-" specific" lectins: Helix pomatia A hemagglutinin, soy bean agglutinin, lima bean lectin, and Dolichos biflorus lectin
    • Hammarstrom, S., Murphy, L. A., Goldstein, I. J., and Etzler, M. E. (1977) Carbohydrate binding specificity of four N-acetyl-D-galactosamine-" specific" lectins: Helix pomatia A hemagglutinin, soy bean agglutinin, lima bean lectin, and Dolichos biflorus lectin, Biochemistry 16, 2750-2755.
    • (1977) Biochemistry , vol.16 , pp. 2750-2755
    • Hammarstrom, S.1    Murphy, L.A.2    Goldstein, I.J.3    Etzler, M.E.4
  • 32
    • 0023946353 scopus 로고
    • Glycolipid-lectin interactions: Reactivity of lectins from Helix pomatia, Wisteria floribunda, and Dolichos biflorus with glycolipids containing N-acetylgalactosamine
    • Torres, B. V., McCrumb, D. K., and Smith, D. F. (1988) Glycolipid-lectin interactions: reactivity of lectins from Helix pomatia, Wisteria floribunda, and Dolichos biflorus with glycolipids containing N-acetylgalactosamine, Arch. Biochem. Biophys. 262, 1-11.
    • (1988) Arch. Biochem. Biophys. , vol.262 , pp. 1-11
    • Torres, B.V.1    McCrumb, D.K.2    Smith, D.F.3
  • 34
    • 0014477665 scopus 로고
    • Oligosaccharides of human milk. I. Isolation and characterization
    • Kobata, A., Ginsburg, V., and Tsuda, M. (1969) Oligosaccharides of human milk. I. Isolation and characterization, Arch. Biochem. Biophys. 130, 509-513.
    • (1969) Arch. Biochem. Biophys. , vol.130 , pp. 509-513
    • Kobata, A.1    Ginsburg, V.2    Tsuda, M.3
  • 36
    • 33750982685 scopus 로고    scopus 로고
    • Chemoenzymatic synthesis of glycan libraries
    • Blixt, O., and Razi, N. (2006) Chemoenzymatic synthesis of glycan libraries, Methods Enzymol. 415, 137-153.
    • (2006) Methods Enzymol. , vol.415 , pp. 137-153
    • Blixt, O.1    Razi, N.2
  • 37
    • 70349300561 scopus 로고    scopus 로고
    • Deciphering Lectin Ligands through Glycan Arrays
    • (Vasta, G. R., Ahmed, H., Eds.) CRC Press, New York
    • Smith, D. F., Cummings, R. D. (2008) Deciphering Lectin Ligands through Glycan Arrays, in Animal Lectins: A Functional View (Vasta, G. R., Ahmed, H., Eds.) pp 49-62, CRC Press, New York.
    • (2008) Animal Lectins: A Functional View , pp. 49-62
    • Smith, D.F.1    Cummings, R.D.2
  • 38
    • 45749107540 scopus 로고    scopus 로고
    • Deciphering the glycosaminoglycan code with the help of microarrays
    • de Paz, J. L., and Seeberger, P. H. (2008) Deciphering the glycosaminoglycan code with the help of microarrays, Mol. Biosyst. 4, 707-711.
    • (2008) Mol. Biosyst. , vol.4 , pp. 707-711
    • De Paz, J.L.1    Seeberger, P.H.2
  • 40
    • 53049085180 scopus 로고    scopus 로고
    • Glycoconjugate microarray based on an evanescent-field fluorescence-assisted detection principle for investigation of glycan-binding proteins
    • Tateno, H., Mori, A., Uchiyama, N., Yabe, R., Iwaki, J., Shikanai, T., Angata, T., Narimatsu, H., and Hirabayashi, J. (2008) Glycoconjugate microarray based on an evanescent-field fluorescence-assisted detection principle for investigation of glycan-binding proteins, Glycobiology 18, 789-798.
    • (2008) Glycobiology , vol.18 , pp. 789-798
    • Tateno, H.1    Mori, A.2    Uchiyama, N.3    Yabe, R.4    Iwaki, J.5    Shikanai, T.6    Angata, T.7    Narimatsu, H.8    Hirabayashi, J.9
  • 42
    • 0242608336 scopus 로고    scopus 로고
    • Carbohydrate microarrays
    • Wang, D. (2003) Carbohydrate microarrays, Proteomics 3, 2167-2175.
    • (2003) Proteomics , vol.3 , pp. 2167-2175
    • Wang, D.1
  • 43
    • 28544438397 scopus 로고    scopus 로고
    • Versatile fluorescent derivatization of glycans for glycomic analysis
    • DOI 10.1038/nmeth808, PII N808
    • Xia, B., Kawar, Z. S., Ju, T., Alvarez, R. A., Sachdev, G. P., and Cummings, R. D. (2005) Versatile fluorescent derivatization of glycans for glycomic analysis, Nat. Methods 2, 845-850. (Pubitemid 41741535)
    • (2005) Nature Methods , vol.2 , Issue.11 , pp. 845-850
    • Xia, B.1    Kawar, Z.S.2    Ju, T.3    Alvarez, R.A.4    Sachdev, G.P.5    Cummings, R.D.6
  • 44
    • 0029670645 scopus 로고    scopus 로고
    • The Le(x) carbohydrate sequence is recognized by antibody to L5, a functional antigen in early neural development
    • Streit, A., Yuen, C. T., Loveless, R. W., Lawson, A. M., Finne, J., Schmitz, B., Feizi, T., and Stern, C. D. (1996) The Le(x) carbohydrate sequence is recognized by antibody to L5, a functional antigen in early neural development, J. Neurochem. 66, 834-844. (Pubitemid 26036717)
    • (1996) Journal of Neurochemistry , vol.66 , Issue.2 , pp. 834-844
    • Streit, A.1    Yuen, C.-T.2    Loveless, R.W.3    Lawson, A.M.4    Finne, J.5    Schmitz, B.6    Feizi, T.7    Stern, C.D.8
  • 45
    • 0032817981 scopus 로고    scopus 로고
    • Influence of oligosaccharide presentation on the interactions of carbohydrate sequence-specific antibodies and the selectins. Observations with biotinylated oligosaccharides
    • DOI 10.1016/S0022-1759(99)00077-0, PII S0022175999000770
    • Leteux, C., Stoll, M. S., Childs, R. A., Chai, W., Vorozhaikina, M., and Feizi, T. (1999) Influence of oligosaccharide presentation on the interactions of carbohydrate sequence-specific antibodies and the selectins. Observations with biotinylated oligosaccharides, J. Immunol. Methods 227, 109-119. (Pubitemid 29408709)
    • (1999) Journal of Immunological Methods , vol.227 , Issue.1-2 , pp. 109-119
    • Leteux, C.1    Stoll, M.S.2    Childs, R.A.3    Chai, W.4    Vorozhaikina, M.5    Feizi, T.6
  • 46
    • 33750993048 scopus 로고    scopus 로고
    • Preparation of Neoglycolipids with Ring-Closed Cores via Chemoselective Oxime-Ligation for Microarray Analysis of Carbohydrate-Protein Interactions
    • DOI 10.1016/S0076-6879(06)15020-X, PII S007668790615020X, Glycobiology
    • Liu, Y., Chai, W., Childs, R. A., and Feizi, T. (2006) Preparation of neoglycolipids with ring-closed cores via chemoselective oxime-ligation for microarray analysis of carbohydrate-protein interactions, Methods Enzymol. 415, 326-340. (Pubitemid 44751106)
    • (2006) Methods in Enzymology , vol.415 , pp. 326-340
    • Liu, Y.1    Chai, W.2    Childs, R.A.3    Feizi, T.4
  • 47
    • 25444514510 scopus 로고    scopus 로고
    • Facile preparation of carbohydrate microarrays by site-specific, covalent immobilization of unmodified carbohydrates on hydrazide-coated glass slides
    • Lee, M. R., and Shin, I. (2005) Facile preparation of carbohydrate microarrays by site-specific, covalent immobilization of unmodified carbohydrates on hydrazide-coated glass slides, Org. Lett. 7, 4269-4272.
    • (2005) Org. Lett. , vol.7 , pp. 4269-4272
    • Lee, M.R.1    Shin, I.2
  • 48
    • 61849087823 scopus 로고    scopus 로고
    • Construction of carbohydrate microarrays by using one-step, direct immobilizations of diverse unmodified glycans on solid surfaces
    • Park, S., Lee, M. R., and Shin, I. (2009) Construction of carbohydrate microarrays by using one-step, direct immobilizations of diverse unmodified glycans on solid surfaces, Bioconjugate Chem. 20, 155-162.
    • (2009) Bioconjugate Chem. , vol.20 , pp. 155-162
    • Park, S.1    Lee, M.R.2    Shin, I.3
  • 49
    • 33746224346 scopus 로고    scopus 로고
    • Fabrication of carbohydrate microarrays on gold surfaces: Direct attachment of non-derivatized oligosaccharides to hydrazide-modified self-assembled monolayers
    • Zhi, Z. L., Powell, A. K., and Turnbull, J. E. (2006) Fabrication of carbohydrate microarrays on gold surfaces: direct attachment of non-derivatized oligosaccharides to hydrazide-modified self-assembled monolayers, Anal. Chem. 78, 4786-4793.
    • (2006) Anal. Chem. , vol.78 , pp. 4786-4793
    • Zhi, Z.L.1    Powell, A.K.2    Turnbull, J.E.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.