Rapid, sensitive sequencing of oligosaccharides from glycoproteins

Current Opinion in Biotechnology

Volumn 8, Issue 4, 1997, Pages 488-497

  Rudd, Pauline M ^a   Dwek, Raymond A ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCAN; GLYCOPROTEIN; GLYCOSIDASE; IMMUNOGLOBULIN G; OLIGOSACCHARIDE;

ANALYTIC METHOD; CARBOHYDRATE ANALYSIS; DATA BASE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MOLECULAR MODEL; POLYACRYLAMIDE GEL ELECTROPHORESIS; PRIORITY JOURNAL; PROTEIN ANALYSIS; PROTEIN PURIFICATION; PROTEIN STRUCTURE; REVIEW;

EID: 0030839756     PISSN: 09581669     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0958-1669(97)80073-0     Document Type: Article

References (50)

1. Rudd PM, Dwek RA: Glycosylation, heterogeneity and the 3D structure of proteins. Crit Rev Biochem Mol Biol 1997, 32:1-100. A review of recent research into the role of glycosylation inside and outside the cell, including some applications of the recently developed technology for profiling and sequencing oligosaccharides using a combination of HPLC and simultaneous sequencing of glycan pools.
2. Dwek RA, Edge CJ, Harvey DJ, Wormald MW, Parekh RB: Analysis of glycoprotein associated oligosaccharides. Annu Rev Biochem 1993, 62:65-100.
3. Gooley AA, Williams KL: How to find, identify and quantitate the sugars on proteins. Nature 1997, 385:557-559. This paper describes a new protein sequenator which allows the recovery of glycosylated amino acids and which can be used for the identification, quantitation and characterisation of sites of glycosylation on proteins. This technique makes it possible to analyse the glycosylation at serine and threonine sites in mucin-like domains. A major hurdle to be overcome in order to make this system more generally applicable is the development of a reliable means of sequencing the oligosaccharides.
4. Patel TP, Parekh RB: Release of oligosaccharides from proteins by hydrazinolysis. Methods Enzymol 1994, 230:57-66.
5. Tarentino AL, Quinones G, Schrader WP, Changchien L-M, Plummer TH Jr: Multiple endoglycosidase (Endo) F activities expressed by Flavobacterium meningosepticum. Endo F1: molecular cloning, primary sequence, and structural relationship to Endo H. J Biol Chem 1992, 267:3868-3972.
6. Tarentino AL, Quinones G, Plummer TH Jr: Overexpression and purification of non-glycosylated recombinant endo-β-N-acetylglucosaminidase F3. Glycobiology 1995, 5:599-601.
7. O'Neill RA: Enzymatic release of oligosaccharides from glycoproteins for chromatographic and electrophoretic analysis. J Chromatogr A 1996, 720:201-215. An excellent review of the current position regarding the sources and specificity of the endo-glycosidases and glycoamidases used for oligosaccharide release.
8. Bigge JC, Patel TP, Bruce JA, Goulding PN, Charles SM, Parekh RB: Nonselective and efficient fluorescent labeling of glycans using 2-amino benzamide and anthranilic acid. Anal Biochem 1995, 230:229-238.
9. Jackson P, Pluskal MG, Skea W: The use of polyacrylamide gel electrophoresis for the analysis of acidic glycans labelled with the fluorophore 2-aminoacridone. Biochemistry 1994, 15:896-902.
10. Jackson P: The analysis of fluorophore-labelled carbohydrates by polyacrylamide gel electrophoresis. Mol Biotechnol 1996 5:101-176. A useful review describing the applications and potential of a PAGE system for analysing released oligosaccharides.
11. Honda S, Makino A, Suzuki S, Kakehi K: Analysis of the oligosaccharides in ovalbumin by high-performance capillary electrophoresis. Anal Biochem 1990, 191:228-234.
12. Jackson P: Polyacrylamide gel electrophoresis of reducing saccharides labeled with the fluorophore 2-aminoacridone: subpicomolar detection using an imaging system based on a cooled charge-coupled device. Anal Biochem 1991, 196:238-244.
13. Okafo G, Burrow L, Carr S, Roberts GD, Johnson W, Camelleri P: A co-ordinated high performance liquid chromatographic, capillary electrophoretic and mass spectrometric approach for the analysis of oligosaccharide mixtures derivatised with 2-aminoacridone. Anal Chem 1996, 68:4424-4430. This paper illustrates how several analytical systems may be co-ordinated to assign oligosaccharide structures. Oligosaccharide labelling with 2-AA is compatible with all these techniques.
14. Guttman A, Chen F-TA, Evangelista A, Cooke N: High-resolution capillary gel electrophoresis of reducing oligosaccharides labelled with 1-aminopyrene-3,6,8-trisulphonate. Anal Biochem 1996, 233:234-242.
15. Huddleston MJ, Bean MF, Carr SA: Collisional fragmentation of glycopeptides by electrospray ionisation LC/MS and LC/MS/MS - methods for selective detection of glycopeptides in protein digests. Anal Chem 1993, 65:877-884.
16. Merkle RK, Poppe I: Carbohydrate composition analysis of glycoconjugates by gas-liquid chromatography/mass spectrometry. Methods Enzymol 1994, 230:1-15.
17. Kovacik V, Hirsch P, Kovac P, Heerma W, Thomas-Oates J, Haverkamp J: Oligosaccharide characterisation using collision induced decomposition fast atom bombardment mass spectrometry: evidence for internal monosaccharide residue loss. J Mass Spectr 1995, 30:949-958.
18. Spengler B, Kirsch D, Kaufmann R, Lemoine J: Structure analysis of branched oligosaccharides using post source decay in matrix assisted laser desorption-ionisation mass spectrometry. Org Mass Spectrom 1994, 29:782-787.
19. Harvey DJ, Naven TJP, Kuster B, Bateman RH, Green, MR, Critchley G: Comparison of fragmentation modes for the structural determination of complex oligosaccharides ionised by matrix-assisted laser desorption-ionisation mass spectrometry. Rapid Commun Mass Spectrom 1995, 9:1556-1561.
20. Reinhold VN, Reinhold BB, Costello CE: Carbohydrate molecular weight profiling, sequence, linkage and branching data: ES/MS and collision induced decomposition. Anal Chem 1995, 67:1772-1784.
21. Harvey D, Bateman RH, Green MR: High collision-induced fragmentation of complex oligosaccharides ionised by matrix-assisted laser desorption/ionisation mass spectrometry. J Mass Spectrom 1997, 32:167-187. This paper describes the production of glycosidic cleavages and cross-ring cleavages, and the formation of internal cleavage ions using a double focusing mass spectrometer fitted with a tandem orthogonal acceleration TOF analyser.
22. Morris HR, Paxton T, Dell A, Langhorne J, Berg M, Bordoli RS, Hoyes J, Bateman RH: High-sensitivity collisionally-activated decomposition tandem mass-spectrometry on a novel quadrupole/orthogonal-acceleration time-of-flight mass-spectrometer. Rapid Comm Mass Spectrom 1996, 10:889-896. This paper explores the use of a novel TOF mass spectrometer to record collisionally activated decomposition spectra
23. Apffel A, Chakel JA, Hancock WS, Souders C, M'Timkulu T, Pungor E Jr: Application of high performance liquid chromatography-electrospray ionisation mass spectrometry and matrix-assisted laser-desorption ionisation time of flight mass spectrometry in combination with selective enzymatic modifications in the characterisation of glycosylation patterns in single-chain plasminogen activator. J Chromatogr 1996, 732:27-42. This study, in common with [24], describes the application of MS technology to the site-specific analysis of glycoproteins of biological interest.
24. Schindler PA, Settiner CA, Collet X, Felding CJ, Burlingame AL: Site-specific detection and structural characterisation of the glycosylation of human plasma proteins lecithin:cholesterol acyltransferase and apolipoprotein D using HPLC/electrospray mass spectrometry and sequential glycosidase digestion. Protein Sci 1995, 4:791-803.
25. Takao T, Tambara Y, Nakamura A, Yoshino K-i, Fukada H, Fukuda M, Shimonishi Y: Sensitive analysis of oligosaccharides derivatised with 4-aminobenzoic acid 2-(diethylamino)ethyl ester by matrix assisted laser desorption-ionisation mass spectrometry. Rapid Commun Mass Spectrom 1996, 10:637-640.
26. Zhao Y, Kent SBH, Chait BT: Rapid, sensitive structure analysis of oligosaccharides. Proc Natl Acad Sci USA 1997, 94:1629-1633.
27. Powell AK, Harvey DJ: Stabilisation of sialic acids in N-linked oligosaccharides and gangliosides for analysis by positive ion matrix-assisted laser desorption ionisation mass spectrometry. Rapid Comm Mass Spectrom 1996, 10:1027-1032.
28. Naven TJP, Harvey DJ: Cationic derivatisation of oligosaccharides with Girard's T reagent for improved performance in matrix-assisted laser desorption/ionisation and electrospray mass spectrometry. Rapid Comm Mass Spectrom 1996, 10:829-834. The increase in sensitivity achieved by derivativising oligosaccharides with Girard T reagent is only of the order of 10%. This method is useful, however, for overcoming the problems associated with noncarbohydrate artefacts which may be erroneously identified as glycans because they have identical molecular weights to oligosaccharides.
29. Kakehi K, Honda S: Analysis of glycoproteins, glycopeptides and glycoprotein-derived oligosaccharides by high-performance capillary electrophoresis. J Chromatography A 1996, 720:377-393. This useful review describes recent advances in the separation of glycoforms, glycopeptides and oligosaccharides, including the use of precolumn derivatisation and the 2 D mapping of carbohydrate chains.
30. Honda S: Separation of neutral carbohydrates by capillary electrophoresis. J Chromatogr A 1996, 720:337-351.
31. Novotny MV: Glycoconjugate analysis by capillary electrophoresis. Methods Enzymol 1996, 271:319-347. This comprehensive review discusses the instrumentation and columns available for performing CE and contains many examples of oligosaccharide and monosaccharide separations. The use of fluorescent tagging is also reviewed.
32. Camilleri P, Harland GB, Okafo G: High resolution and rapid analysis of branched oligosaccharides by capillary electrophoresis. Anal Biochem 1995, 230:115-122.
33. Harland GB, Okafo G, Sellick IC, Chapman GE, Camilleri P: Fingerprinting of glycans as their 2-aminoacridone derivatives by capillary electrophoresis and laser induced fluorescence. Electrophoresis 1996, 17:406-411. This study demonstrates the sensitivity and resolving power of CE fitted with LIF detection to profile 2-AA oligosaccharide derivatives.
34. Okafo GN, Burrow LM, Neville W, Truneh A, Smith RAG, Reff M, Camilleri P: Simple differentiation between core-fucosylated and non-fucosylated glycans by capillary electrophoresis. Anal Biochem 1996, 240:68-74.
35. Rudd PM, Joao HC, Coghill E, Fiten P, Saunders MR, Opdenakker G, Dwek RA: Glycoforms modify the dynamic stability and functional activity of an enzyme. Biochemistry 1994, 33:17-22.
36. Iourin O, Mattu T, Mian N, Kier G, Winchester B, Dwek RA, Rudd PM: The identification of abnormal glycoform populations of serum transferrin from carbohydrate deficient glycoprotein syndrome type I by capillary electrophoresis. Glycoconjugate J 1996, 13:1031-1042. This study demonstrates the use of CE to resolve transferrin glycoforms containing complex sugars. Transferrin from normal and carbohydrate-deficient glycoprotein syndrome type I serum is compared. CE is fast, quantitative and easily automated and this study suggests a possible application of the technique in diagnosis.
37. Klausen NK, Kornfelt T: Analysis of the glycoforms of human recombinant factor V11a by capillary electrophoresis and high-performance liquid chromatography. J Chromatogr A 1995, 718:195-202.
38. Guile GR, Rudd PM, Wing DR, Prime SB, Dwek RA: A rapid high resolution method for separating oligosaccharide mixtures and analysing sugarprints. Anal Biochem 1996, 240:210-226. This study describes a sensitive technology capable of resolving subpicomolar quantities of mixtures containing both neutral and charged fluorescently labelled oligosaccharides in a single run using normal phase HPLC. It describes how incremental values for the addition of monosaccharides to oligosaccharide cores are calculated, enabling the prediction of structures from the elution positions of oligosaccharides.
39. Wormald MW, Rudd PM, Harvey DH, Chang S-C, Scragg IG, Dwek RA: Variations in oligosaccharide-protein interactions in immunoglobulin G determine the site specific glycosylation profiles and modulate the dynamic motion of the Fc oligosaccharides. Biochemistry 1997, 36:1370-1380. This paper demonstates the combined use of exoglycosidases and HPLC to analyse the glycan pool released from IgG.
40. Guile GR, Wong SYC, Dwek RA: Analytical and preparative separation of anionic oligosaccharides by weak anion-exchange high-performance liquid chromatography on an inert polymer column. Anal Biochem 1994, 222:231-235.
41. Davies MJ, Hounsell EF: Comparison of separation modes of high performance liquid chromatography for the analysis of glycoprotein and proteoglycan-derived oligosaccharides. J Chromatogr 1996, 720:227-233. A useful comparison of HPLC separation modes which also describes the use of porous graphite columns for resolving sulphated oligosaccharides released from proteoglycans.
42. Lund J, Takahasi N, Pound J, Goodall M, Jefferis R: Multiple interactions of IgG with its core oligosaccharide can modulate recognition by complement and human FcgR1, and influence the synthesis of its oligosaccharide chains. J Immunol 1996, 157:4963-4969.
43. Nakagawa H, Kawamura Y, Kato K, Shimada I, Arata Y, Takahashi N: Identification of neutral and sialyl N-linked oligosaccharide structures from human serum glycoproteins using three different kinds of high performance liquid chromatography. Anal Biochem 1995, 226:130-138.
44. Takahashi N, Nakagawa H, Fujikawa K, Kawamura Y, Tomiya N: Three-dimensional elution mapping of pyridylaminated N-linked neutral and sialyl oligosaccharides. Anal Biochem 1995, 226:139-146.
45. Nakagawa H, Zheng M, Hakomori S, Tsukamoto Y, Kawamura Y, Takahashi, N: Detailed oligosaccharide structures of human integrin α5β1 analysed by a three-dimensional mapping technique. Eur J Biochem 1996, 237:76-85. This study demonstrates an application of the 3D mapping technique which is used to identify 35 different oligosaccharides associated with integrin α5β1 purified from human placenta. Along with [48], which gives an example of the use of comparative 2D gel electrophoresis to indicate differences between normal and diseased serum, this technique has many potential applications both in diagnosing disease and in studying disease pathogenesis.
46. Edge CJ, Rademacher TW, Wormald MR, Parekh RB, Butters TD, Wing DR, Dwek RA: Fast sequencing of oligosaccharides: the reagent array analysis method. Proc Natl Acad Sci USA 1992, 89:6338-6342.
47. Rudd PM, Morgan BP, Wormald MR, Harvey DJ, van den Berg CW, Davis SJ, Ferguson MAJ, Dwek RA: The glycosylation of the complement regulatory protein, CD59, derived from human erythrocytes and human platelets. J Biol Chem 1997, in press. The rapid profiling and analysis of the glycans attached to human erythrocyte CD59 using a combination of predictive normal phase HPLC and the simultaneous sequencing of aliquots of the entire glycan pool using enzyme arrays.
48. Harrison HH, Miller KL: Multiple serum protein abnormalities in carbohydrate-deficient glycoprotein syndrome: pathogenomonic finding of two-dimensional electrophoresis. Clin Chem 1992, 38:1390-1392.
49. Küster B, Wheeler SF, Hunter AP, Dwek RA, Harvey DJ: Sequencing of N-linked oligosaccharides directly from protein gels: in gel deglycosylation followed by matrix assisted laser desorption/ionisation, mass spectrometry and normal phase high performance liquid chromatography. Anal Biochem 1997, in press. This paper describes the release and sequencing of N-linked oligosaccharides from SDS gel bands.
50. Küster B, Naven TJP, Harvey DJ: Rapid approach for sequencing neutral oligosaccharides by exoglycosidase digestion and matrix-assisted laser desorption ionisation time-of-flight mass spectrometry. J Mass Spectrom 1996, 31:1131-1140.