Transglycosylation-based fluorescent labeling of 6-gala series glycolipids by endogalactosylceramidase

Glycobiology

Volumn 19, Issue 7, 2009, Pages 797-807

  Ishibashi, Yohei ^a   Nagamatsu, Yusuke ^a   Meyer, Sandra ^b   Imamura, Akihiro ^c,d   Ishida, Hideharu ^c   Kiso, Makoto ^c,d   Okino, Nozomu ^a   Geyer, Rudolf ^b   Ito, Makoto ^a,b,e  

^a KYUSHU UNIVERSITY   (Japan)

^b JUSTUS LIEBIG UNIVERSITY   (Germany)

^c GIFU UNIVERSITY   (Japan)

^d KYOTO UNIVERSITY   (Japan)

^e NEW ENERGY AND INDUSTRIAL TECHNOLOGY DEVELOPMENT ORGANIZATION   (Japan)

Author keywords

6 gala series glycosphingolipids; Endogalactosylceramidase; Fluorescence derivatization; Transglycosylation reaction

Indexed keywords

4 CHLORO 7 NITROBENZOFURAZAN; ALKANOL; CERAMIDE; DECANOL; DIGALACTOSYLDIGLYCERIDE; ENDOGALACTOSYLCERAMIDASE; GALACTOSYLCERAMIDASE; GLYCOGLYCEROLIPID; GLYCOLIPID; GLYCOSPHINGOLIPID; OLIGOSACCHARIDE; PENTANOL; UNCLASSIFIED DRUG;

ARTICLE; CARBOHYDRATE ANALYSIS; CHEMICAL LABELING; CONTROLLED STUDY; DERIVATIZATION; ENZYME GLYCOSYLATION; ENZYME MECHANISM; ENZYME SPECIFICITY; FLUORESCENCE ANALYSIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INTERMETHOD COMPARISON; LIPID ANALYSIS; LIPID HYDROLYSIS; LIPOGENESIS; NONHUMAN; PRIORITY JOURNAL; RHIZOPUS ORYZAE; TAENIA CRASSICEPS; THIN LAYER CHROMATOGRAPHY;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CHROMATOGRAPHY, THIN LAYER; FLUORESCENCE; FLUORESCENT DYES; GLYCOSIDE HYDROLASES; GLYCOSPHINGOLIPIDS; GLYCOSYLATION; STAINING AND LABELING;

FUNGI; MOLLUSCA; RHIZOPUS ORYZAE; TAENIA CRASSICEPS;

EID: 66249112827     PISSN: 09596658     EISSN: 14602423     Source Type: Journal    
DOI: 10.1093/glycob/cwp051     Document Type: Article

References (42)

1. Anumula KR. 2006. Advances in fluorescence derivatization methods for high-performance liquid chromatographic analysis of glycoprotein carbohydrates. Anal Biochem. 350:1-23.
2. Aoki K, Uchiyama R, Yamauchi S, Katayama T, Itonori S, Sugita M, Hada N, Yamada-Hada J, Takeda T, Kumagai H, et al. 2004. Newly discovered neutral glycosphingolipids in aureobasidin A-resistant Zygomycetes - Identification of a novel family of gala-series glycolipids with core Gal alpha 1-6Gal beta 1-6Gal beta sequences. J Biol Chem. 279:32028-32034.
3. Bigge JC, Patel TP, Bruce JA, Goulding PN, Charles SM, Parekh RB. 1995. Nonselective and efficient fluorescent labeling of glycans using 2-amino benzamide and anthranilic acid. Anal Biochem. 230:229-238.
4. Charlwood J, Birrell H, Gribble A, Burdes V, Tolson D, Camilleri P. 2000. A probe for the versatile analysis and characterization of N linked oligosaccharides. Anal Chem. 72:1453-1461.
5. Chen FT, Evangelista RA. 1995. Analysis of mono- and oligosaccharide isomers derivatized with 9-aminopyrene-1,4,6-trisulfonate by capillary electrophoresis with laser-induced fluorescence. Anal Biochem. 230:273-280.
6. Chiesa C, Horvath C. 1993. Capillary zone electrophoresis of maltooligosaccharides derivatized with 8-aminonaphthalene-1,3,6-trisulfonic acid. J Chromatogr. 645:337-352.
7. Dennis RD, Baumeister S, Geyer R, Peter-Katalinic J, Hartmann R, Egge H, Geyer E, Wiegandt H. 1992. Glycosphingolipids in cestodes. Chemical structures of ceramide monosaccharide, disaccharide, trisaccharide and tetrasaccharide from metacestodes of the fox tapeworm, Taenia crassiceps (Cestoda: Cyclophyllidea). Eur J Biochem. 207:1053-1062.
8. Dennis RD, Baumeister S, Irmer G, Gasser RB, Geyer E. 1993. Chromatographic and antigenic properties of Echinococcus granulosus hydatid cyst-derived glycolipids. Parasite Immunol. 15:669-681.
9. Dennis RD, Geyer R, Egge H, Menges H, Stirm S, Wiegandt H. 1985. Glycosphingolipids in insects. Chemical structures of ceramide monosaccharide, disaccharide, and trisaccharide from pupae of Calliphora vicina (Insecta: Diptera). Eur J Biochem. 146:51-58.
10. Guile GR, Rudd PM, Wing DR, Prime SB, Dwek RA. 1996. A rapid high-resolution high-performance liquid chromatographic method for separating glycan mixtures and analyzing oligosaccharide profiles. Anal Biochem. 240:210-226.
11. Hase S, Ibuki T, Ikenaka T. 1984. Reexamination of the pyridylamination used for fluorescence labeling of oligosaccharides and its application to glycoproteins. J Biochem. 95:197-203.
12. Hase S, Ikenaka T, Matsushima Y. 1978. Structure analyses of oligosaccharides by tagging of the reducing end sugars with a fluorescent compound. Biochem Biophys Res Commun. 85:257-263.
13. Hase S, Ikenaka T, Matsushima Y. 1981. A highly sensitive method for analyses of sugar moieties of glycoproteins by fluorescence labeling. J Biochem. 90:407-414.
14. Hayashi A, Matsubara T. 1989. A new homolog of phosphonoglycosphingolipid, N methylaminoethylphosphonyltrigalactosylceramide. Biochim Biophys Acta. 1006:89-96.
15. Higashi H, Ito M, Fukaya N, Yamagata S, Yamagata T. 1990. Two-dimensional mapping by the high-performance liquid chromatography of oligosaccharides released from glycosphingolipids by endoglycoceramidase. Anal Biochem. 186:355-362.
16. Holzl G, Witt S, Kelly AA, Zahringer U, Warnecke D, Dormann P, Heinz E. 2006. Functional differences between galactolipids and glucolipids revealed in photosynthesis of higher plants. Proc Natl Acad Sci USA 103:7512-7517.
17. Iriko H, Nakamura K, Kojima H, Iida-Tanaka N, Kasama T, Kawakami Y, Ishizuka I, Uchida A, Murata Y, Tamai Y. 2002. Chemical structures and immunolocalization of glycosphingolipids isolated from Diphyllobothrium hottai adult worms and plerocercoids. Eur J Biochem. 269:3549-3559.
18. Ishibashi Y, Kiyohara M, Okino N, Ito M. 2007. Synthesis of fluorescent glycosphingolipids and neoglycoconjugates which contain 6-gala oligosaccharides using the transglycosylation reaction of a novel endoglycoceramidase (EGALC). J Biochem. 142:239-246.
19. Ishibashi Y, Nakasone T, Kiyohara M, Horibata Y, Sakaguchi K, Hijikata A, Ichinose S, Omori A, Yasui Y, Imamura A, et al. 2007. A novel endoglycoceramidase hydrolyzes oligogalactosylceramides to produce galactooligosaccharides and ceramides. J Biol Chem. 282:11386-11396.
20. Kawakami Y, Nakamura K, Kojima H, Suzuki M, Inagaki F, Suzuki A, Ikuta J, Uchida A, Murata Y, Tamai Y. 1996. Novel fucosyltetrahexosylceramide in plerocercoids of the parasite Spirometra erinacei. Eur J Biochem 239:905-911.
21. Kelly AA, Dormann P. 2004. Green light for galactolipid trafficking. Curr Opin Plant Biol. 7:262-269.
22. Landoni M, Duschak VG, Erra-Balsells R, Couto AS. 2008. UV-MALDI mass spectrometry analysis of NBD-glycosphingolipids without an external matrix. J Am Soc Mass Spectrom. 19:923-926.
23. Lemoine J, Cabanes-Macheteau M, Bardor M, Michalski JC, Faye L, Lerouge P. 2000. Analysis of 8-aminonaphthalene-1,3,6-trisulfonic acid labelled N-glycans by matrix-assisted laser desorption/ionisation time-of-flight mass spectrometry. Rapid Commun Mass Spectrom. 14:100-104.
24. Matsubara T, Hayashi A. 1981. Structural studies on glycolipid of shellfich: 3. Novel glycolipids from Turbo cornutus. J Biochem. 89:645-650.
25. Matsubara T, Hayashi A. 1986. Structural studies on glycolipids of hellfish: 5. Gala-6 series glycosphingolipids of the marine snail, Chlorostoma argyrostoma turbinatum. J Biochem. 99:1401-1408.
26. McManus DP, Zhang W, Li J, Bartley PB. 2003. Echinococcosis. Lancet 362:1295-1304.
27. Neville DCA, Coquard V, Priestman DA, Te Vruchte DJM, Sillence DJ, Dwek RA, Platt FM, Butters TD. 2004. Analysis of fluorescently labeled glycosphingolipid-derived oligosaccharides following ceramide glycanase digestion and anthranilic acid labeling. Anal Biochem. 331:275-282.
28. Nishimura K, Suzuki A, Kino H. 1991. Sphingolipids of a cestode Metroliasthes coturnix. Biochim Biophys Acta. 1086:141-150.
29. Noda N, Tanaka R, Miyahara K, Sukamoto T. 1996. Six trigalactosylceramides from the leech (Hirudo nipponica). Chem Pharm Bull. 44:895-899.
30. Ohara K, Sano M, Kondo A, Kato I. 1991. Two-dimensional mapping by high-performance liquid chromatography of pyridylamino oligosaccharides from various glycosphingolipids. J Chromatogr. 586:35-41.
31. Okafo G, Langridge J, North S, Organ A, West A, Morris M, Camilleri P. 1997. High-performance liquid chromatographic analysis of complex N linked glycans derivatized with 2-aminoacridone. Anal Chem. 69:4985-4993.
32. Orlowski M. 1991. Mucor dimorphism. Microbiol Rev. 55:234-258.
33. Persat F, Bouhours JF, Mojon M, Petavy AF. 1992. Glycosphingolipids with Gal-beta-1-6Gal sequences in metacestodes of the parasite Echinococcus multilocularis. J Biol Chem. 267:8764-8769.
34. Persat F, Vincent C, Schmitt D, Mojon M. 1996. Inhibition of human peripheral blood mononuclear cell proliferative response by glycosphingolipids from metacestodes of Echinococcus multilocularis. Infect Immun. 64:3682-3687.
35. Sugita M, Fujii H, Inagaki F, Suzuki M, Hayata C, Hori T. 1992. POLAR glycosphingolipids in annelida - A novel series of glycosphingolipids containing choline phosphate from the earthworm. Pheretima hilgendorfi. J Biol Chem. 267:22595-22598.
36. Sugita M, Hayata C, Suzuki M, Takeda T, Mizunoma T, Makino T, Narushima K, Hori T. 1992. Isolation and charaterization of neutral glycosphingolipids from annelida (Earthworm, Pheretime hilgendorfi). J Japan Oil Chem Soc. 41:568-573.
37. Sugita M, Mizunoma T, Inagaki F, Suzuki M, Suzuki A, Hori T, Nakatani F, Ohta S. 1994. Occurrence of novel neogala series glycosphingolipids with a monnnose at the non-reducing terminal in Annelida (earthworm, Pheretima hilgendorfi). J Japan Oil Chem Soc. 43:1052-1061.
38. Sugita M, Morikawa A, Dulaney JT, Okada A. 1996. Glycosphingolipids with Gal alpha 1-6Gal and Gal beta 1-6Gal sequences in the leech, Hirudo nipponia. J Japan Oil Chem Soc. 45:731-740.
39. Sugita M, Ohta S, Morikawa A, Dulaney JT, Ichikawa S, Kushida K, Inagaki F, Suzuki M, Suzuki A. 1997. Novel neogala series glycosphingolipids with glucose at the non-reducing termini in the earthworm, Pheretima sp. J Japan Oil Chem Soc. 46:755-766.
40. Tomiya N, Awaya J, Kurono M, Endo S, Arata Y, Takahashi N. 1988. Analyses of N-linked oligosaccharides using a two-dimensional mapping technique. Anal Biochem. 171:73-90.
41. Wang WT, LeDonne NC Jr, Ackerman B, Sweeley CC. 1984. Structural characterization of oligosaccharides by high-performance liquid chromatography, fast-atom bombardment-mass spectrometry, and exoglycosidase digestion. Anal Biochem. 141:366-381.
42. Wing DR, Garner B, Hunnam V, Reinkensmeier G, Andersson U, Harvey DJ, Dwek RA, Platt FM, Butters TD. 2001. High-performance liquid chromatography analysis of ganglioside carbohydrates at the picomole level after ceramide glycanase digestion and fluorescent labeling with 2-aminobenzamide. Anal Biochem. 298:207-217.