Generation of a natural glycan microarray using 9-fluorenylmethyl chloroformate (FmocCl) as a cleavable fluorescent tag

Analytical Biochemistry

Volumn 395, Issue 2, 2009, Pages 151-160

  Song, Xuezheng ^a   Lasanajak, Yi ^a   Rivera Marrero, Carlos ^a   Luyai, Anthony ^a   Willard, Margaret ^a   Smith, David F ^a   Cummings, Richard D ^a  

^a EMORY UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Fluorescent labeling; Functional glycomics; Glycan array; Immobilization

Indexed keywords

ANTIBODIES; BIOASSAY; BIOSYNTHESIS; FLUORESCENCE; GLYCOPROTEINS; MAMMALS; PEPTIDES; RADIOACTIVE WASTE VITRIFICATION;

9-FLUORENYLMETHYL CHLOROFORMATE; FLUORESCENT LABELING; GLYCAN ARRAY; GLYCOMICS; HORSERADISH PEROXIDASE; PROTEASE DIGESTION; PROTEIN-CARBOHYDRATE INTERACTIONS; SCHISTOSOMA MANSONI;

POLYSACCHARIDES;

9 FLUORENYLMETHYL CHLOROFORMATE; FETUIN; FLUORESCENT DYE; GLYCAN; GLYCOPEPTIDE; GLYCOPROTEIN; HORSERADISH PEROXIDASE; IMMUNOGLOBULIN G ANTIBODY; IMMUNOGLOBULIN M ANTIBODY; N HYDROXYSUCCINIMIDE; OVALBUMIN; PLANT LECTIN; PRONASE; PROTEINASE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIBODY RESPONSE; ARTICLE; CONJUGATION; CONTROLLED STUDY; DEPROTECTION REACTION; DERIVATIZATION; FLUORESCENCE ANALYSIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MICROARRAY ANALYSIS; MOUSE; NONHUMAN; PRIORITY JOURNAL; PROTEIN CLEAVAGE; PROTEIN DEGRADATION; PROTEIN MICROARRAY; PROTEIN PURIFICATION; QUANTITATIVE ANALYSIS; SCHISTOSOMA MANSONI; SCHISTOSOMIASIS MANSONI; SEPARATION TECHNIQUE;

ARMORACIA RUSTICANA; BOVINAE; MUS; SCHISTOSOMA MANSONI;

EID: 70349783548     PISSN: 00032697     EISSN: 10960309     Source Type: Journal    
DOI: 10.1016/j.ab.2009.08.024     Document Type: Article

References (61)

1. Varki A., Cummings R.D., Esko J.D., Freeze H.H., Stanley P., Bertozzi C.R., Hart G.W., and Etzler M.E. Essentials of Glycobiology (2009), Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY
2. Taniguchi N., Hancock W., Lubman D.M., and Rudd P.M. The second golden age of glycomics: from functional glycomics to clinical applications. J. Proteome Res. 8 (2009) 425-426
3. Alvarez R.A., and Blixt O. Identification of ligand specificities for glycan-binding proteins using glycan arrays. Methods Enzymol. 415 (2006) 292-310
4. Paulson J.C., Blixt O., and Collins B.E. Sweet spots in functional glycomics. Nat. Chem. Biol. 2 (2006) 238-248
5. Blixt O., Head S., Mondala T., Scanlan C., Huflejt M.E., Alvarez R., Bryan M.C., Fazio F., Calarese D., Stevens J., Razi N., Stevens D.J., Skehel J.J., van Die I., Burton D.R., Wilson I.A., Cummings R., Bovin N., Wong C.H., and Paulson J.C. Printed covalent glycan array for ligand profiling of diverse glycan binding proteins. Proc. Natl. Acad. Sci. USA 101 (2004) 17033-17038
6. Drickamer K., and Taylor M.E. Glycan arrays for functional glycomics. Genome Biol. 3 (2002) (Reviews 1034)
7. Feizi T., and Chai W. Oligosaccharide microarrays to decipher the glyco code. Nat. Rev. Mol. Cell. Biol. 5 (2004) 582-588
8. Park S., Lee M.R., and Shin I. Chemical tools for functional studies of glycans. Chem. Soc. Rev. 37 (2008) 1579-1591
9. Lopez P.H., and Schnaar R.L. Determination of glycolipid-protein interaction specificity. Methods Enzymol. 417 (2006) 205-220
10. Magnani J.L., Brockhaus M., Smith D.F., and Ginsburg V. Detection of glycolipid ligands by direct binding of carbohydrate-binding proteins to thin-layer chromatograms. Methods Enzymol. 83 (1982) 235-241
11. Feizi T., Fazio F., Chai W., and Wong C.H. Carbohydrate microarrays-a new set of technologies at the frontiers of glycomics. Curr. Opin. Struct. Biol. 13 (2003) 637-645
12. Liu Y., Feizi T., Campanero-Rhodes M.A., Childs R.A., Zhang Y., Mulloy B., Evans P.G., Osborn H.M., Otto D., Crocker P.R., and Chai W. Neoglycolipid probes prepared via oxime ligation for microarray analysis of oligosaccharide-protein interactions. Chem. Biol. 14 (2007) 847-859
13. Disney M.D., and Seeberger P.H. The use of carbohydrate microarrays to study carbohydrate-cell interactions and to detect pathogens. Chem. Biol. 11 (2004) 1701-1707
14. de Boer A.R., Hokke C.H., Deelder A.M., and Wuhrer M. General microarray technique for immobilization and screening of natural glycans. Anal. Chem. 79 (2007) 8107-8113
15. Song X., Xia B., Lasanajak Y., Smith D.F., and Cummings R.D. Quantifiable fluorescent glycan microarrays. Glycoconj. J. 25 (2008) 15-25
16. Park S., Lee M.R., and Shin I. Fabrication of carbohydrate chips and their use to probe protein-carbohydrate interactions. Nat. Protoc. 2 (2007) 2747-2758
17. Park S., Lee M.R., Pyo S.J., and Shin I. Carbohydrate chips for studying high-throughput carbohydrate-protein interactions. J. Am. Chem. Soc. 126 (2004) 4812-4819
18. Park S., and Shin I. Fabrication of carbohydrate chips for studying protein-carbohydrate interactions. Angew. Chem. Int. Ed. Engl. 41 (2002) 3180-3182
19. Ratner D.M., Adams E.W., Su J., O'Keefe B.R., Mrksich M., and Seeberger P.H. Probing protein-carbohydrate interactions with microarrays of synthetic oligosaccharides. Chembiochem 5 (2004) 379-382
20. Bryan M.C., Fazio F., Lee H.K., Huang C.Y., Chang A., Best M.D., Calarese D.A., Blixt O., Paulson J.C., Burton D., Wilson I.A., and Wong C.H. Covalent display of oligosaccharide arrays in microtiter plates. J. Am. Chem. Soc. 126 (2004) 8640-8641
21. Bigge J.C., Patel T.P., Bruce J.A., Goulding P.N., Charles S.M., and Parekh R.B. Nonselective and efficient fluorescent labeling of glycans using 2-amino benzamide and anthranilic acid. Anal. Biochem. 230 (1995) 229-238
22. Bohorov O., Andersson-Sand H., Hoffmann J., and Blixt O. Arraying glycomics: a novel bi-functional spacer for one-step microscale derivatization of free reducing glycans. Glycobiology 16 (2006) 21C-27C
23. Xia B., Kawar Z.S., Ju T., Alvarez R.A., Sachdev G.P., and Cummings R.D. Versatile fluorescent derivatization of glycans for glycomic analysis. Nat. Methods 2 (2005) 845-850
24. Song X., Xia B., Stowell S.R., Lasanajak Y., Smith D.F., and Cummings R.D. Novel fluorescent glycan microarray strategy reveals ligands for galectins. Chem. Biol. 16 (2009) 36-47
25. Arsequell G., Dwek R.A., and Wong S.Y. 9-Fluorenylmethoxycarbonyl (Fmoc)-glycine coupling of saccharide beta-glycosylamines for the fractionation of oligosaccharides and the formation of neoglycoconjugates. Anal. Biochem. 216 (1994) 165-170
26. Seko A., Koketsu M., Nishizono M., Enoki Y., Ibrahim H.R., Juneja L.R., Kim M., and Yamamoto T. Occurence of a sialylglycopeptide and free sialylglycans in hen's egg yolk. Biochim. Biophys. Acta 1335 (1997) 23-32
27. Liu X., Li X., Chan K., Zou W., Pribil P., Li X.F., Sawyer M.B., and Li J. "One-pot" methylation in glycomics application: esterification of sialic acids and permanent charge construction. Anal. Chem. 79 (2007) 3894-3900
28. Liu X., McNally D.J., Nothaft H., Szymanski C.M., Brisson J.R., and Li J. Mass spectrometry-based glycomics strategy for exploring N-linked glycosylation in eukaryotes and bacteria. Anal. Chem. 78 (2006) 6081-6087
29. Narahashi Y. Pronase. Methods Enzymol. 19 (1970) 651-664
30. Nisbet A.D., Saundry R.H., Moir A.J., Fothergill L.A., and Fothergill J.E. The complete amino-acid sequence of hen ovalbumin. Eur. J. Biochem. 115 (1981) 335-345
31. Ogata S., Muramatsu T., and Kobata A. Fractionation of glycopeptides by affinity column chromatography on concanavalin A-Sepharose. J. Biochem. 78 (1975) 687-696
32. Krusius T., Finne J., and Rauvala H. The structural basis of the different affinities of two types of acidic N-glycosidic glycopeptides for concanavalin A-Sepharose. FEBS Lett. 72 (1976) 117-120
33. Baenziger J.U., and Fiete D. Structural determinants of Ricinus communis agglutinin and toxin specificity for oligosaccharides. J. Biol. Chem. 254 (1979) 9795-9799
34. Narasimhan S., Freed J.C., and Schachter H. The effect of a "bisecting" N-acetylglucosaminyl group on the binding of biantennary, complex oligosaccharides to concanavalin A, Phaseolus vulgaris erythroagglutinin (E-PHA), and Ricinus communis agglutinin (RCA-120) immobilized on agarose. Carbohydr. Res. 149 (1986) 65-83
35. Kornfeld K., Reitman M.L., and Kornfeld R. The carbohydrate-binding specificity of pea and lentil lectins. Fucose is an important determinant. J. Biol. Chem. 256 (1981) 6633-6640
36. Corradi Da Silva M.L., Stubbs H.J., Tamura T., and Rice K.G. 1H NMR characterization of a hen ovalbumin tyrosinamide N-linked oligosaccharide library. Arch. Biochem. Biophys. 318 (1995) 465-475
37. Takahashi N., Lee K.B., Nakagawa H., Tsukamoto Y., Masuda K., and Lee Y.C. New N-glycans in horseradish peroxidase. Anal. Biochem. 255 (1998) 183-187
38. Yang B.Y., Gray J.S., and Montgomery R. The glycans of horseradish peroxidase. Carbohydr. Res. 287 (1996) 203-212
39. Wilson I.B., and Altmann F. Concanavalin A binding and endoglycosidase D resistance of beta1, 2-xylosylated and alpha1, 3-fucosylated plant and insect oligosaccharides. Glycoconj. J. 15 (1998) 203-206
40. Yamashita K., Kochibe N., Ohkura T., Ueda I., and Kobata A. Fractionation of L-fucose-containing oligosaccharides on immobilized Aleuria aurantia lectin. J. Biol. Chem. 260 (1985) 4688-4693
41. Jang-Lee J., Curwen R.S., Ashton P.D., Tissot B., Mathieson W., Panico M., Dell A., Wilson R.A., and Haslam S.M. Glycomics analysis of Schistosoma mansoni egg and cercarial secretions. Mol. Cell. Proteomics 6 (2007) 1485-1499
42. Khoo K.H., Chatterjee D., Caulfield J.P., Morris H.R., and Dell A. Structural mapping of the glycans from the egg glycoproteins of Schistosoma mansoni and Schistosoma japonicum: identification of novel core structures and terminal sequences. Glycobiology 7 (1997) 663-677
43. Khoo K.H., Huang H.H., and Lee K.M. Characteristic structural features of Schistosome cercarial N-glycans: expression of Lewis X and core xylosylation. Glycobiology 11 (2001) 149-163
44. Nyame A.K., Leppanen A.M., Bogitsh B.J., and Cummings R.D. Antibody responses to the fucosylated LacdiNAc glycan antigen in Schistosoma mansoni-infected mice and expression of the glycan among schistosomes. Exp. Parasitol. 96 (2000) 202-212
45. Simpson A.J., Ali P.O., Yi X.Y., and Smithers S.R. Schistosome glycoconjugates as antigens and their relevance in experimental and human schistosomiasis. Biochem. Soc. Trans. 16 (1988) 264-265
46. Hokke C.H., and Deelder A.M. Schistosome glycoconjugates in host-parasite interplay. Glycoconj. J. 18 (2001) 573-587
47. Thomas P.G., and Harn Jr. D.A. Immune biasing by helminth glycans. Cell Microbiol. 6 (2004) 13-22
48. van Die I., and Cummings R.D. Glycans modulate immune responses in helminth infections and allergy. Chem. Immunol. Allergy 90 (2006) 91-112
49. van Remoortere A., Bank C.M., Nyame A.K., Cummings R.D., Deelder A.M., and van Die I. Schistosoma mansoni-infected mice produce antibodies that cross-react with plant, insect, and mammalian glycoproteins and recognize the truncated biantennaryN-glycan Man3GlcNAc2-R. Glycobiology 13 (2003) 217-225
50. Fields G.B., and Noble R.L. Solid phase peptide synthesis utilizing 9-fluorenylmethoxycarbonyl amino acids. Int. J. Pept. Protein Res. 35 (1990) 161-214
51. Wellings D.A., and Atherton E. Standard Fmoc protocols. Methods Enzymol. 289 (1997) 44-67
52. Cudic M., and Burstein G.D. Preparation of glycosylated amino acids suitable for Fmoc solid-phase assembly. Methods Mol. Biol. 494 (2008) 187-208
53. Garg H.G., von dem Bruch K., and Kunz H. Developments in the synthesis of glycopeptides containing glycosyl l-asparagine, l-serine, and l-threonine. Adv. Carbohydr. Chem. Biochem. 50 (1994) 277-310
54. Kihlberg J., Elofsson M., and Salvador L.A. Direct synthesis of glycosylated amino acids from carbohydrate peracetates and Fmoc amino acids: solid-phase synthesis of biomedicinally interesting glycopeptides. Methods Enzymol. 289 (1997) 221-245
55. Lavielle S., Ling N.C., and Guillemin R.C. Solid-phase synthesis of two glycopeptides containing the amino acid sequence 5 to 9 of somatostatin. Carbohydr. Res. 89 (1981) 221-228
56. Liu M., Barany G., and Live D. Parallel solid-phase synthesis of mucin-like glycopeptides. Carbohydr. Res. 340 (2005) 2111-2122
57. Norberg T., Luning B., and Tejbrant J. Solid-phase synthesis of O-glycopeptides. Methods Enzymol. 247 (1994) 87-106
58. Altmann F., Schweiszer S., and Weber C. Kinetic comparison of peptide: N-glycosidases F and A reveals several differences in substrate specificity. Glycoconj. J. 12 (1995) 84-93
59. Chai W., Feizi T., Yuen C.T., and Lawson A.M. Nonreductive release of O-linked oligosaccharides from mucin glycoproteins for structure/function assignments as neoglycolipids: application in the detection of novel ligands for E-selectin. Glycobiology 7 (1997) 861-872
60. Hounsell E.F., Pickering N.J., Stoll M.S., Lawson A.M., and Feizi T. The effect of mild alkali and alkaline borohydride on the carbohydrate and peptide moieties of fetuin. Biochem. Soc. Trans. 12 (1984) 607-610
61. Huang Y., Mechref Y., and Novotny M.V. Microscale nonreductive release of O-linked glycans for subsequent analysis through MALDI mass spectrometry and capillary electrophoresis. Anal. Chem. 73 (2001) 6063-6069