Structure determination by MALDI-IRMPD mass spectrometry and exoglycosidase digestions of O-linked oligosaccharides from Xenopus borealis egg jelly

Glycobiology

Volumn 21, Issue 7, 2011, Pages 877-894

  Li, Bensheng ^a,b   Russell, Scott C ^a,c   Zhang, Jinhua ^a,d   Hedrick, Jerry L ^a   Lebrilla, Carlito B ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b BUCK INSTITUTE FOR RESEARCH ON AGING   (United States)

^c CALIFORNIA STATE UNIVERSITY   (United States)

^d GENENTECH INC   (United States)

Author keywords

exoglycosidase; MALDI IRMPD mass spectrometry; O glycan structure; tandem MS; X. borealis

Indexed keywords

EGG WHITE; EXOGLYCOSIDASE; GLYCAN; GLYCOPROTEIN; GLYCOSIDASE; OLIGOSACCHARIDE; UNCLASSIFIED DRUG;

ARTICLE; CARBOHYDRATE ANALYSIS; EGG; MATRIX ASSISTED LASER DESORPTION IONIZATION INFRARED MULTIPHOTON DISSOCIATION TANDEM MASS SPECTROMETRY; NONHUMAN; PRIORITY JOURNAL; TANDEM MASS SPECTROMETRY; XENOPUS; XENOPUS BOREALIS;

ANIMALS; CARBOHYDRATE CONFORMATION; CARBOHYDRATE SEQUENCE; GLYCOSIDE HYDROLASES; GLYCOSYLATION; MOLECULAR SEQUENCE DATA; OLIGOSACCHARIDES; OVUM; PHYLOGENY; POLYSACCHARIDES; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; XENOPUS;

XENOPODINAE; XENOPUS BOREALIS; XENOPUS LAEVIS;

EID: 79958863877     PISSN: 09596658     EISSN: 14602423     Source Type: Journal    
DOI: 10.1093/glycob/cwr003     Document Type: Article

References (47)

1. Agard NJ, Bertozzi CR. 2009. Chemical approaches to perturb, profile, and perceive glycans. Acc Chem Res. 42:788-797.
2. Apweiler R, Hermjakob H, Sharon N. 1999. On the frequency of protein gly-cosylation, as deduced from analysis of the SWISS-PROT database. Biochim Biophys Acta. 1473:4-8.
3. Brockhausen I. 1999. Pathways of O-glycan biosynthesis in cancer cells. Biochim Biophys Acta. 1473:67-95.
4. Brooks SA. 2006. Protein glycosylation in diverse cell systems: Implications for modification and analysis of recombinant proteins. Expert Rev Proteomics. 3:345-359. (Pubitemid 43979408)
5. Brun R, Kobel HR. 1977. Observations on fertilization block between Xenopus borealis and Xenopus laevis laevis. J Exp Zool. 201:135-137.
6. Busch C, Aktories K. 2000. Microbial toxins and the glycosylation of rho family GTPases. Curr Opin Struct Biol. 10:528-535.
7. Cyster JG, Shotton DM, Williams AF. 1991. The dimensions of the T lymphocyte glycoprotein leukosialin and identification of linear protein epi-topes that can be modified by glycosylation. EMBO J. 10:893-902. (Pubitemid 21905547)
8. Dell A, Morris HR, Easton RL, Patankar M, Clark GF. 1999. The glycobiology of gametes and fertilization. Biochim Biophys Acta. 1473:196-205.
9. Easton RL, Patankar MS, Lattanzio FA, Leaven TH, Morris HR, Clark GF, Dell A. 2000. Structural analysis of murine zona pellucida glycans. Evidence for the expression of core 2-type O-glycans and the Sd(a) antigen. J Biol Chem. 275:7731-7742. (Pubitemid 30159677)
10. Endo T. 1999. O-Mannosyl glycans in mammals. Biochim Biophys Acta. 1473:237-246.
11. Evans BJ, Kelley DB, Tinsley RC, Melnick DJ, Cannatella DC. 2004. A mitochondrial DNA phylogeny of African clawed frogs: Phylogeography and implications for polyploid evolution. Mol Phylog Evol. 33:197-213. (Pubitemid 39138745)
12. Freeze HH. 2006. Genetic defects in the human glycome. Nat Rev. 7:537-551. (Pubitemid 43943571)
13. Gerwig GJ, Kamerling JP, Vliegenthart JF, Morag E, Lamed R, Bayer EA. 1993. The nature of the carbohydrate-peptide linkage region in glyco-proteins from the cellulosomes of Clostridium thermocellum and Bacteroides cellulosolvens. J Biol Chem. 268:26956-26960. (Pubitemid 24006404)
14. Goldberg D, Bern M, Li B, Lebrilla CB. 2006. Automatic determination of O-glycan structure from fragmentation spectra. J Proteome Res. 5:1429-1434. (Pubitemid 43865812)
15. Guerardel Y, Kol O, Maes E, Lefebvre T, Boilly B, Davril M, Strecker G. 2000. O-glycan variability of egg-jelly mucins from Xenopus laevis: Characterization of four phenotypes that differ by the terminal glycosyla-tion of their mucins. Biochem J. 352(Pt 2):449-463. (Pubitemid 32011439)
16. 35S]-sulfate in the jelly coat of Xenopus laevis eggs. Biol Reprod. 11:534-542.
17. Helenius A, Aebi M. 2001. Intracellular functions of N-linked glycans. Science. 291:2364-2369. (Pubitemid 32231791)
18. Hirohashi N, Kamei N, Kubo H, Sawada H, Matsumoto M, Hoshi M. 2008. Egg and sperm recognition systems during fertilization. Dev Growth Differ. 50(Suppl. 1):S221-S238. (Pubitemid 351725081)
19. Horrocks AJ, Stewart S, Jackson L, Wishart GJ. 2000. Induction of acrosomal exocytosis in chicken spermatozoa by inner perivitelline-derived N-linked glycans. Biochem Biophys Res Commun. 278:84-89.
20. Kirmiz C, Li B, An HJ, Clowers BH, Chew HK, Lam KS, Ferrige A, Alecio R, Borowsky AD, Sulaimon S., et al. 2007. A serum glycomics approach to breast cancer biomarkers. Mol Cell Proteomics. 6:43-55. (Pubitemid 46152690)
21. Lancaster KS, An HJ, Li B, Lebrilla CB. 2006. Interrogation of N-Linked oligosaccharides using infrared multiphoton dissociation in FT-ICR mass spectrometry. Anal Chem. 78:4990-4997. (Pubitemid 44100635)
22. Lauc G, Rudan I, Campbell H, Rudd PM. 2010. Complex genetic regulation of protein glycosylation. Mol Biosyst. 6:329-335.
23. Li B, An HJ, Hedrick JL, Lebrilla CB. 2009a. Collision-induced dissociation tandem mass spectrometry for structural elucidation of glycans. Methods Mol Biol. 534:133-145.
24. Li B, An HJ, Hedrick JL, Lebrilla CB. 2009b. Infrared multiphoton dissociation mass spectrometry for structural elucidation of oligosaccharides. Methods Mol Biol. 534:23-35.
25. Lindsay LL, Peavy TR, Lejano RS, Hedrick JL. 2003. Cross-fertilization and structural comparison of egg extracellular matrix glycoproteins from Xenopus laevis and Xenopus tropicalis. Comp Biochem Physiol. 136:343-352. (Pubitemid 37153374)
26. Lindsay LL, Yang JC, Hedrick JL. 2002. Identification and characterization of a unique Xenopus laevis egg envelope component, ZPD. Dev Growth Differ. 44:205-212. (Pubitemid 34639366)
27. Mann K, Mechling DE, Bachinger HP, Eckerskorn C, Gaill F, Timpl R. 1996. Glycosylated threonine but not 4-hydroxyproline dominates the triple helix stabilizing positions in the sequence of a hydrothermal vent worm cuticle collagen. J Mol Biol. 261:255-266. (Pubitemid 26275807)
28. McLeskey SB, Dowds C, Carballada R, White RR, Saling PM. 1998. Molecules involved in mammalian sperm-egg interaction. Int Rev Cytol. 177:57-113. (Pubitemid 128716721)
29. Nishimura H, Yamashita S, Zeng Z, Walz DA, Iwanaga S. 1992. Evidence for the existence of O-linked sugar chains consisting of glucose and xylose in bovine thrombospondin. J Biochem. 111:460-464.
30. Ohtsubo K, Marth JD. 2006. Glycosylation in cellular mechanisms of health and disease. Cell. 126:855-867. (Pubitemid 44310784)
31. Plancke Y, Wieruszeski JM, Alonso C, Boilly B, Strecker G. 1995. Structure of four acidic oligosaccharides from the jelly coat surrounding the eggs of Xenopus laevis. Eur J Biochem. 231:434-439.
32. Prasad SV, Skinner SM, Carino C, Wang N, Cartwright J, Dunbar BS. 2000. Structure and function of the proteins of the mammalian zona pellucida. Cells Tissues Organs. 166:148-164. (Pubitemid 30163553)
33. Spiro RG. 2002. Protein glycosylation: Nature, distribution, enzymatic formation, and disease implications of glycopeptide bonds. Glycobiology. 12:43R-56R. (Pubitemid 34760066)
34. Strecker G, Wieruszeski JM, Plancke Y, Boilly B. 1995. Primary structure of 12 neutral oligosaccharide-alditols released from the jelly coats of the anuran Xenopus laevis by reductive β-elimination. Glycobiology. 5:137-146.
35. Szymanski CM, Wren BW. 2005. Protein glycosylation in bacterial mucosal pathogens. Nat Rev. 3:225-237. (Pubitemid 40298222)
36. Tseng K, Hedrick JL, Lebrilla CB. 1999. Catalog-library approach for the rapid and sensitive structural elucidation of oligosaccharides. Anal Chem. 71:3747-3754.
37. Tseng K, Lindsay LL, Penn S, Hedrick JL, Lebrilla CB. 1997. Characterization of neutral oligosaccharide-alditols from Xenopus laevis egg jelly coats by matrix-assisted laser desorption Fourier transform mass spectrometry. Anal Biochem. 250:18-28. (Pubitemid 27310309)
38. Tseng K, Xie Y, Seeley J, Hedrick JL, Lebrilla CB. 2001. Profiling with structural elucidation of the neutral and anionic O-linked oligosaccharides in the egg jelly coat of Xenopus laevis by Fourier transform mass spectrometry. Glycoconj J. 18:309-320. (Pubitemid 34123744)
39. Vilela-Silva AC, Hirohashi N, Mourao PA. 2008. The structure of sulfated polysaccharides ensures a carbohydrate-based mechanism for species recognition during sea urchin fertilization. Int J Dev Biol. 52:551-559.
40. Wassarman PM. 1999. Mammalian fertilization: Molecular aspects of gamete adhesion, exocytosis, and fusion. Cell. 96:175-183. (Pubitemid 29059348)
41. Wyrick RE, Nishihara T, Hedrick JL. 1974. Agglutination of jelly coat and cortical granule components and the block to polyspermy in the amphibian Xenopus laevis. Proc Natl Acad Sci USA. 71:2067-2071.
42. Xie Y, Lebrilla CB. 2003. Infrared multiphoton dissociation of alkali metal-coordinated oligosaccharides. Anal Chem. 75:1590-1598. (Pubitemid 36512596)
43. Xie Y, Liu J, Zhang J, Hedrick JL, Lebrilla CB. 2004. Method for the comparative glycomic analyses of O-linked, mucin-type oligosaccharides. Anal Chem. 76:5186-5197. (Pubitemid 39180351)
44. Xie Y, Tseng K, Lebrilla CB, Hedrick JL. 2001. Targeted use of exoglycosi-dase digestion for the structural elucidation of neutral O-linked oligosac-charides. J Am Soc Mass Spectrom. 12:877-884. (Pubitemid 34552670)
45. Zhang J, Lindsay LL, Hedrick JL, Lebrilla CB. 2004. Strategy for profiling and structure elucidation of mucin-type oligosaccharides by mass spec-trometry. Anal Chem. 76:5990-6001. (Pubitemid 39382945)
46. Zhang J, Schubothe K, Li B, Russell S, Lebrilla CB. 2005. Infrared multipho-ton dissociation of O-linked mucin-type oligosaccharides. Anal Chem. 77:208-214. (Pubitemid 40096688)
47. Zhang J, Xie Y, Hedrick JL, Lebrilla CB. 2004. Profiling the morphological distribution of O-linked oligosaccharides. Anal Biochem. 334:20-35. (Pubitemid 39304072)