Modern developments in mass spectrometry of chondroitin and dermatan sulfate glycosaminoglycans

Amino Acids

Volumn 41, Issue 2, 2011, Pages 235-256

  Sisu, Eugen ^a,b   Flangea, Corina ^c   Serb, Alina ^a   Zamfir, Alina D ^c,d  

^a VICTOR BABES UNIVERSITY OF MEDICINE AND PHARMACY   (Romania)

^b ACADEMY OF ROMANIAN SCIENTISTS   (Romania)

^c VASILE GOLDIS WESTERN UNIVERSITY OF ARAD   (Romania)

^d Development in Electrochemistry and Condensed Matter   (Romania)

Author keywords

Capillary electrophoresis; Chip nanoESI; Chondroitin dermatan sulfate; ESI; HPLC; MALDI; Mass spectrometry; Review; Screening; Sequencing

Indexed keywords

CHONDROITIN SULFATE; DERMATAN SULFATE;

CAPILLARY ELECTROPHORESIS; CARBOHYDRATE ANALYSIS; CHEMICAL REACTION; CLINICAL PROTOCOL; COLLISIONALLY ACTIVATED DISSOCIATION; ELECTRON DETACHMENT DISSOCIATION; ELECTROSPRAY MASS SPECTROMETRY; FRAGMENTATION REACTION; HUMAN; ION CYCLOTRON RESONANCE MASS SPECTROMETRY; ISOLATION PROCEDURE; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; NANOANALYSIS; NANOCHIP; NONHUMAN; ONLINE ANALYTICAL PROCESSING; PRIORITY JOURNAL; PROCESS DEVELOPMENT; PROTEIN PURIFICATION; PROTEOGLYCAN SYNTHESIS; REVIEW; SEPARATION TECHNIQUE; STRUCTURE ACTIVITY RELATION;

ANIMALS; CARBOHYDRATE SEQUENCE; CHONDROITIN SULFATES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DERMATAN SULFATE; ELECTROPHORESIS, CAPILLARY; GLYCOSAMINOGLYCANS; HUMANS; MASS SPECTROMETRY; PROTEOGLYCANS; SEQUENCE ANALYSIS;

EID: 79960242680     PISSN: 09394451     EISSN: 14382199     Source Type: Journal    
DOI: 10.1007/s00726-010-0682-4     Document Type: Review

References (84)

1. M Ambrosius K Kleesiek C Götting 2008 Quantitative determination of the glycosaminoglycan Δ-disaccharide composition of serum, platelets, and granulocytes by reversed-phase high-performance liquid chromatography J Chromatogr A 1201 54 60 18586257 10.1016/j.chroma.2008.06.007 1:CAS:528:DC%2BD1cXosFSnsbg%3D
2. S Amon AD Zamfir A Rizzi 2008 Glycosylation analysis of glycoproteins and proteoglycans using capillary electrophoresis-mass spectrometry strategies Electrophoresis 29 2485 2507 18512669 10.1002/elps.200800105 1:CAS:528:DC%2BD1cXosFymsb8%3D (Pubitemid 351911877)
3. X Bao MSG Pavao JC dos Santos K Sugahara 2005 A functional dermatan sulfate epitope containing iduronate(2-O-sulfate)alpha1-3GalNAc(6-O-sulfate) disaccharide in the mouse brain: demonstration using a novel monoclonal antibody raised against dermatan sulfate of ascidian Ascidia nigra J Biol Chem 280 23184 23193 15849184 10.1074/jbc.M503036200 1:CAS:528:DC%2BD2MXltVyhu78%3D (Pubitemid 40853230)
4. B Barroso M Didraga R Bischoff 2005 Analysis of proteoglycans derived sulphated disaccharides by liquid chromatography/mass spectrometry J Chromatogr A 1080 43 48 16013613 10.1016/j.chroma.2005.03.020 1:CAS:528: DC%2BD2MXltFeitrs%3D (Pubitemid 40804986)
5. K Busse M Averbeck U Anderegg K Arnold JC Simon J Schiller 2006 The signal-to-noise ratio as a measure of HA oligomer concentration: a MALDI TOF MS study Carbohydr Res 341 1065 1070 16584713 10.1016/j.carres.2006.03.005 1:CAS:528:DC%2BD28XksFeqtr0%3D
6. L Chi JJ Wolff TN Laremore OF Restaino J Xie C Schiraldi T Toida J Amster RJ Linhardt 2008 Structural analysis of bikunin glycosaminoglycan J Am Chem Soc 130 2617 2625 18247611 10.1021/ja0778500 1:CAS:528:DC%2BD1cXhsVKksro%3D (Pubitemid 351307798)
7. D Cointe Y Leroy F Chirat 1998 Determination of the sialylation level and of the ratio α(2-3)/α(2-6) sialyl linkages of n-glycans by methylation and GC/MS analysis Carbohydr Res 311 51 59 9821266 10.1016/S0008-6215(98)00196-7 1:CAS:528:DyaK1cXmvFOqurg%3D (Pubitemid 28461910)
8. JA Deakin M Lyon 2008 A simplified and sensitive fluorescent method for disaccharide analysis of both heparan sulfate and chondroitin/dermatan sulfates from biological samples Glycobiology 18 483 491 18378523 10.1093/glycob/cwn028 1:CAS:528:DC%2BD1cXmvFSmtr8%3D (Pubitemid 351753552)
9. SS Deepa K Kalayanamitra Y Ito P Kongtawelert P Fukui S Yamada T Mikami K Sugahara 2007 Novel sulfated octa- and decasaccharides from squid cartilage chondroitin sulfate E: sequencing and application for determination of the epitope structure of the monoclonal antibody MO-225 Biochemistry 46 2453 2465 17284053 10.1021/bi602374m 1:CAS:528:DC%2BD2sXhtlGlsLY%3D (Pubitemid 46362419)
10. H Desaire LT Sirich JA Leary 2001 Evidence of block and randomly sequenced chondroitin polysaccharides: sequential enzymatic digestion and quantification using ion trap tandem mass spectrometry Anal Chem 73 3513 3520 11510812 10.1021/ac010385j 1:CAS:528:DC%2BD3MXkvVSgsrY%3D (Pubitemid 32862355)
11. JM Dethy BL Ackermann C Delatour JD Henion GA Schultz 2003 Demonstration of direct bioanalysis of drugs in plasma using nanoelectrospray infusion from a silicon chip coupled with tandem mass spectrometry Anal Chem 75 805 811 12622370 10.1021/ac0260692 1:CAS:528:DC%2BD3sXjvFemtA%3D%3D (Pubitemid 36232433)
12. B Domon CE Costello 1988 A systematic nomenclature for carbohydrate fragmentations in FAB-MS/MS spectra of glycoconjugates Glycoconj J 5 397 409 10.1007/BF01049915 1:CAS:528:DyaL1MXitVyks7g%3D (Pubitemid 19031141)
13. RP Estrella JM Whitelock NH Packer NG Karlsson 2007 Graphitized carbon LC-MS characterization of the chondroitin sulfate oligosaccharides of aggrecan Anal Chem 79 3597 3606 17411012 10.1021/ac0622227 1:CAS:528:DC%2BD2sXjvVKgsb4%3D (Pubitemid 46799054)
14. NS Fedarko 2001 Purification of proteoglycans from mineralized tissues Methods Mol Biol 171 19 25 11450229 1:CAS:528:DC%2BD3MXkslKjs78%3D
15. C Flangea AF Serb C Schiopu S Tudor E Sisu DG Seidler AD Zamfir 2009 Discrimination of GalNAc (4S/6S) sulfation sites in chondroitin sulfate disaccharides by chip-based nanoelectrospray multistage mass spectrometry Cent Eur J Chem 7 752 759 10.2478/s11532-009-0070-7 1:CAS:528:DC%2BD1MXht1Cgu7rK
16. C Flangea C Schiopu E Sisu A Serb M Przybylski DG Seidler AD Zamfir 2009 Determination of sulfation pattern in brain glycosaminoglycans by chip-based electrospray ionization ion trap mass spectrometry Anal Bioanal Chem 395 2489 2498 19826794 10.1007/s00216-009-3167-0 1:CAS:528:DC%2BD1MXhsVCitL7F
17. Fuchs B, Arnold K, Schiller J (2008) In: Meyers RA (ed) Encyclopedia of analytical chemistry. Wiley, Chichester, p 1
18. A Hamai N Hashimoto H Mochizuki F Kato Y Makiguchi K Horie S Suzuki 1997 Two distinct chondroitin sulfate ABC lyases: An endoeliminase yielding tetrasaccharides and an exoeliminase preferentially acting on oligosaccharides J Biol Chem 272 9123 9130 9083041 10.1074/jbc.272.14.9123 1:CAS:528: DyaK2sXisVGrurc%3D (Pubitemid 27154917)
19. MJ Hernáiz RJ Linhardt 2001 Degradation of chondroitin sulfate and dermatan sulfate with chondroitin lyases Methods Mol Biol 171 363 371 11450250
20. AM Hitchcock CE Costello J Zaia 2006 Glycoform quantification of chondroitin/dermatan sulfate using a liquid chromatography-tandem mass spectrometry platform Biochemistry 45 2350 2361 16475824 10.1021/bi052100t 1:CAS:528:DC%2BD28XoslOgtQ%3D%3D (Pubitemid 43271335)
21. AM Hitchcock KE Yates CE Costello J Zaia 2008 Comparative glycomics of connective tissue glycosaminoglycans Proteomics 8 1384 1397 18318007 10.1002/pmic.200700787 1:CAS:528:DC%2BD1cXltVOmsLo%3D (Pubitemid 351518550)
22. P Hu L Fang EK Chess 2009 Source-induced fragmentation of heparin, heparan, and galactosaminoglycans and application Anal Chem 81 2332 2343 19228018 10.1021/ac802626e 1:CAS:528:DC%2BD1MXhs1ajtLg%3D
23. W Huang L Boju L Tkalec H Su HO Yang NS Gunay RJ Linhardt YS Kim A Matte M Cygler 2001 Active site of chondroitin AC lyase revealed by the structure of enzyme-oligosaccharide complexes and mutagenesis Biochemistry 40 2359 2372 11327856 10.1021/bi0024254 1:CAS:528:DC%2BD3MXmvVGmsQ%3D%3D (Pubitemid 32171708)
24. J Kameoka R Orth B Ilic D Czaplewski T Wachs HG Craighead 2002 An electrospray ionization source for integration with microfluidics Anal Chem 74 5897 5901 12463378 10.1021/ac020396s 1:CAS:528:DC%2BD38XnvF2htb0%3D (Pubitemid 35364849)
25. P Kang Y Mechref I Klouckova MV Novotny 2005 Solid-phase permethylation of glycans for mass spectrometric analysis Rapid Commun Mass Spectrom 19 3421 3428 16252310 10.1002/rcm.2210 1:CAS:528:DC%2BD2MXhtlSqtrvM (Pubitemid 41691916)
26. P Kang Y Mechref MV Novotny 2008 High-throughput solid-phase permethylation of glycans prior to mass spectrometry Rapid Commun Mass Spectrom 22 721 734 18265433 10.1002/rcm.3395 1:CAS:528:DC%2BD1cXjvVansLk%3D (Pubitemid 351373956)
27. KH Khoo HR Morris RA McDowell A Dell M Maccarana U Lindahl 1983 FABMS/derivatization strategies for the analysis of heparin derived oligosaccharides Carbohydr Res 244 205 223 10.1016/0008-6215(83)85002-2
28. YG Kim SY Kim YM Hur HS Joo J Chung DS Lee L Royle PM Rudd RA Dwek DJ Harvey BG Kim 2006 The identification and characterization of xenoantigenic nonhuman carbohydrate sequences in membrane proteins from porcine kidney Proteomics 6 1133 1142 16470663 10.1002/pmic.200500275 1:CAS:528: DC%2BD28XitlGgu7Y%3D
29. TN Laremore RJ Linhardt 2007 Improved matrix-assisted laser desorption/ionization mass spectrometric detection of glycosaminoglycan disaccharides as cesium salts Rapid Commun Mass Spectrom 21 1315 1320 17340574 10.1002/rcm.2964 1:CAS:528:DC%2BD2sXks1Grtbg%3D (Pubitemid 46506587)
30. TN Laremore S Murugesan T-J Park FY Avci DV Zagorevski RJ Linhardt 2006 Matrix-assisted laser desorption/ionization mass spectrometric analysis of uncomplexed highly sulfated oligosaccharides using ionic liquid matrices Anal Chem 78 1774 1779 16536411 10.1021/ac051121q 1:CAS:528:DC%2BD28Xht1yhsLw%3D
31. TN Laremore F Zhang RJ Linhardt 2007 Ionic Liquid Matrix for Direct UV-MALDI TOF-MS analysis of dermatan sulfate and chondroitin sulfate oligosaccharides Anal Chem 79 1604 1610 17297962 10.1021/ac061688m 1:CAS:528:DC%2BD28XhtlCgsr7O
32. FE Leach JJ Wolff TN Laremore RJ Linhardt IJ Amster 2008 Evaluation of the experimental parameters which control electron detachment dissociation, and their effect on the fragmentation efficiency of glycosaminoglycan carbohydrates Int J Mass Spectrom 276 110 115 19802340 10.1016/j.ijms.2008.05.017 1:CAS:528:DC%2BD1cXhtVyms7fI
33. M Lei Y Mechref MV Novotny 2009 Structural analysis of sulfated glycans by sequential double-permethylation using methyl iodide and deuteromethyl iodide J Am Soc Mass Spectrom 20 1660 1671 19546010 10.1016/j.jasms.2009.05.001 1:CAS:528:DC%2BD1MXhtV2nt7rE
34. VV Lunin Y Li RJ Linhardt H Miyazono M Kyogashima T Kaneko AW Bell M Cygler 2004 High-resolution crystal structure of Arthrobacter aurescens chondroitin AC lyase: an enzyme-substrate complex defines the catalytic mechanism J Mol Biol 337 367 386 15003453 10.1016/j.jmb.2003.12.071 1:CAS:528:DC%2BD2cXhslemsLY%3D (Pubitemid 38293405)
35. F Matsui A Oohira 2006 Isolation, purification, and analysis of chondroitin sulfate proteoglycans Adv Pharmacol 53 3 20 17239759 10.1016/S1054-3589(05)53001-1 1:CAS:528:DC%2BD1cXhs12qsL0%3D
36. Y Matsuno K Yamada A Tanabe M Kinoshita S-Z Maruyama Y-S Osaka T Masuko K Kakehi 2007 Development of an apparatus for rapid release of oligosaccharides at the glycosaminoglycan-protein linkage region in chondroitin sulfate-type proteoglycans Anal Biochem 362 245 257 17250796 10.1016/j.ab.2006.12.027 1:CAS:528:DC%2BD2sXhvVyntbY%3D (Pubitemid 46227320)
37. JE McClellan CE Costello PB O'Connor J Zaia 2002 Influence of charge state on product ion mass spectra and the determination of 4S/6S sulfation sequence of chondroitin sulfate oligosaccharides Anal Chem 74 3760 3771 12175164 10.1021/ac025506+ 1:CAS:528:DC%2BD38XkvVWhtbs%3D (Pubitemid 34855869)
38. G Michel K Pojasek Y Li T Sulea RJ Linhardt R Raman V Prabhakar R Sasisekharan M Cygler 2004 The structure of chondroitin B lyase complexed with glycosaminoglycan oligosaccharides unravels a calcium-dependent catalytic machinery J Biol Chem 279 32882 32896 15155751 10.1074/jbc.M403421200 1:CAS:528:DC%2BD2cXmtVChurs%3D (Pubitemid 39014748)
39. MJC Miller CE Costello A Malmström J Zaia 2006 A tandem mass spectrometric approach to determination of chondroitin/dermatan sulfate oligosaccharide glycoforms Glycobiology 16 502 513 16489125 10.1093/glycob/ cwj093 1:CAS:528:DC%2BD28XkvVSrs7g%3D (Pubitemid 43779046)
40. M Mormann AD Zamfir DG Seidler H Kresse J Peter-Katalinic 2007 Analysis of over-sulfation in a chondroitin sulfate oligosaccharide fraction from bovine aorta by nanoelectrospray ionization quadrupole time-of-flight and Fourier transform ion cyclotron resonance mass spectrometry J Am Soc Mass Spectrom 18 179 187 17095243 10.1016/j.jasms.2006.09.016 1:CAS:528:DC%2BD2sXht1Wgsrg%3D (Pubitemid 46150095)
41. H Naimy N Leymarie MJ Bowman CE Costello J Zaia 2008 Amide-HILIC LC/MS for the characterization of Antithrombin III heparin binders Biochemistry 47 3155 3161 18260648 10.1021/bi702043e 1:CAS:528:DC%2BD1cXhslCht7c%3D (Pubitemid 351364908)
42. TC Nielsen PJ Meikle JJ Hopwood M Fuller 2008 Minimum substrate requirements of endoglycosidase activities toward dermatan sulfate by electrospray ionization-tandem mass spectrometry Glycobiology 18 1119 1128 18824560 10.1093/glycob/cwn097 1:CAS:528:DC%2BD1cXhsVChtLrE (Pubitemid 352762846)
43. A Nimptsch S Schibura M Schnabelrauch B Fuchs D Huster J Schiller 2009 Characterization of the quantitative relationship between signal-to-noise (S/N) ratio and sample amount on-target by MALDI TOF MS: determination of chondroitin sulfate subsequent to enzymatic digestion Anal Chim Acta 635 175 182 19216875 10.1016/j.aca.2009.01.025 1:CAS:528:DC%2BD1MXit1aitrc%3D
44. T Oguma S Tomatsu AM Montano O Okazaki 2007 Analytical method for the determination of disaccharides derived from keratan, heparan, and dermatan sulfates in human serum and plasma by high-performance liquid chromatography/turbo ionspray ionization tandem mass spectrometry Anal Biochem 368 79 86 17603992 10.1016/j.ab.2007.05.016 1:CAS:528:DC%2BD2sXotVWlsbY%3D (Pubitemid 47058433)
45. K Ohara JC Jacquinet D Jouanneau W Helbert M Smietana JJ Vasseur 2009 Matrix-assisted laser desorption/ionization mass spectrometric analysis of polysulfated-derived oligosaccharides using pyrenemethylguanidine J Am Soc Mass Spectrom 20 131 137 18838278 10.1016/j.jasms.2008.09.004 1:CAS:528: DC%2BD1cXhsFahurnE
46. S Otsuki M Nakajima M Lotz M Kinoshita 2008 Hyaluronic acid and chondroitin sulfate content of osteoarthritic human knee cartilage: site-specific correlation with weight-bearing force based on femorotibial angle measurement J Orthop Res 26 1194 1198 18383185 10.1002/jor.20571
47. K Pojasek Z Shriver P Kiley G Venkataraman R Sasisekharan 2001 Recombinant expression, purification, and kinetic characterization of chondroitinase AC and chondroitinase B from Flavobacterium heparinum Biochem Biophys Res Commun 286 343 351 11500043 10.1006/bbrc.2001.5380 1:CAS:528:DC%2BD3MXlvVejtrw%3D (Pubitemid 32924919)
48. V Prabhakar I Capila CJ Bosques K Pojasek R Sasisekharan 2005 Chondroitinase ABC I from Proteus vulgaris: cloning, recombinant expression and active site identification Biochem J 386 103 112 15691229 10.1042/BJ20041222 1:CAS:528:DC%2BD2MXhtFWmt7k%3D (Pubitemid 40289229)
49. A Purushothaman J Fukuda S Mizumoto GB ten Dam TH van Kuppevelt H Kitagawa T Mikami KJ Sugahara 2007 Functions of chondroitin sulfate/dermatan sulfate chains in brain development. Critical roles of E and iE disaccharide units recognized by a single chain antibody GD3G7 J Biol Chem 282 19442 19452 17500059 10.1074/jbc.M700630200 1:CAS:528:DC%2BD2sXntFWkur0%3D (Pubitemid 47100083)
50. CS Rye SG Withers 2002 Elucidation of the mechanism of polysaccharide cleavage by chondroitin AC lyase from Flavobacterium heparinum J Am Chem Soc 124 9756 9767 12175234 10.1021/ja020627c 1:CAS:528:DC%2BD38XlsFamu7k%3D
51. NB Schwartz M Domowicz 2004 Proteoglycans in brain development Glycoconj J 21 329 341 15514481 10.1023/B:GLYC.0000046278.34016.36 1:CAS:528: DC%2BD2cXptVOgsr4%3D (Pubitemid 39434561)
52. DG Seidler J Peter-Katalinić AD Zamfir 2007 Galactosaminoglycan function and oligosaccharide structure determination Sci World J 19 233 241 (Pubitemid 46294535)
53. NT Seyfried CD Blundell AJ Day A Almond 2005 Preparation and application of biologically active fluorescent hyaluronan oligosaccharides Glycobiology 15 303 312 15496500 10.1093/glycob/cwi008 1:CAS:528:DC%2BD2MXhtV2qsrg%3D (Pubitemid 40347356)
54. K Sugahara S Yamada 2000 Structure and function of oversulfated chondroitin sulfate variants: unique sulfation patterns and neuroregulatory activities Trends Glycosci Glycotechnol 12 321 349 1:CAS:528: DC%2BD3cXovVGhtro%3D
55. 2+ ions on the stability of UDP-sugars and chondroitin synthesis Anal Biochem 365 62 73 17395146 10.1016/j.ab.2007.02. 023 1:CAS:528:DC%2BD2sXkslOisbc%3D (Pubitemid 46617464)
56. T Taguchi M Iwasaki Y Muto K Kitajima S Inoue KH Khoo HR Morris A Dell Y Inoue 1996 Occurrence and structural analysis of highly sulfated multiantennary N-linked glycan chains derived from a fertilization-associated carbohydrate-rich glycoprotein in unfertilized eggs of tribolodon hakonensis Eur J Biochem 238 357 367 8681946 10.1111/j.1432-1033.1996.0357z.x 1:CAS:528:DyaK28XjsVKltbc%3D
57. A Tholey E Heinzle 2006 Ionic (liquid) matrices for matrix-assisted laser desorption/ionization mass spectrometry-applications and perspectives Anal Bioanal Chem 386 24 37 16830111 10.1007/s00216-006-0600-5 1:CAS:528: DC%2BD28Xotl2nu7o%3D (Pubitemid 44268046)
58. B Tissot A Ceroni AK Powell HR Morris EA Yates JE Turnbull JT Gallagher A Dell SM Haslam 2008 Software tool for the structural determination of glycosaminoglycans by mass spectrometry Anal Chem 80 9204 9212 19551986 10.1021/ac8013753 1:CAS:528:DC%2BD1cXhtlSnurjE
59. BP Toole 2004 Hyaluronan: from extracellular glue to pericellular cue Nat Rev Cancer 4 528 539 15229478 10.1038/nrc1391 1:CAS:528:DC%2BD2cXlt1OktrY%3D (Pubitemid 38868622)
60. E Tufvesson A Malmstrom 2002 Biglycan isoforms with differences in polysaccharide substitution and core protein in human lung fibroblasts Eur J Biochem 269 3688 3696 12153565 10.1046/j.1432-1033.2002.03058.x 1:CAS:528:DC%2BD38XmsVSit7c%3D (Pubitemid 34989117)
61. N Volpi 2006 Advances in chondroitin sulfate analysis: application in physiological and pathological States of connective tissue and during pharmacological treatment of osteoarthritis Curr Pharm Des 12 639 658 16472153 10.2174/138161206775474350 1:CAS:528:DC%2BD28XhsVGqs70%3D
62. N Volpi 2007 Analytical aspects of pharmaceutical grade chondroitin sulfates J Pharm Sci 96 3168 3180 17630645 10.1002/jps.20997 1:CAS:528:DC%2BD2sXhsVers7jL
63. N Volpi 2010 High-performance liquid chromatography and on-line mass spectrometry detection for the analysis of chondroitin sulfates/hyaluronan disaccharides derivatized with 2-aminoacridone Anal Biochem 397 12 23 19769935 10.1016/j.ab.2009.09.030 1:CAS:528:DC%2BD1MXhsFyiu7fF
64. N Volpi F Maccari 2009 Structural characterization and antithrombin activity of dermatan sulfate purified from marine clam Scapharca inaequivalvis Glycobiology 19 356 367 19056786 10.1093/glycob/cwn140 1:CAS:528: DC%2BD1MXivFSntb8%3D
65. N Volpi F Maccari RJ Linhardt 2008 Capillary electrophoresis of complex natural polysaccharides Electrophoresis 29 3095 3106 18633943 10.1002/elps.200800109 1:CAS:528:DC%2BD1cXhtV2itbzK
66. M Warda F Zhang M Radwan Z Zhang N Kim YN Kim RJ Linhardt J Han 2008 Is human placenta proteoglycan remodeling involved in pre-eclampsia? Glycoconj J 25 441 450 18161024 10.1007/s10719-007-9090-8 1:CAS:528:DC%2BD1cXmsVKqsrc%3D
67. JJ Wolff L Chi RJ Linhardt IJ Amster 2007 Electron detachment dissociation of glycosaminoglycan tetrasaccharides J Am Soc Mass Spectrom 18 234 244 17074503 10.1016/j.jasms.2006.09.020 1:CAS:528:DC%2BD2sXht1Wgs70%3D (Pubitemid 46150099)
68. JJ Wolff TN Laremore H Aslam RJ Linhardt IJ Amster 2008 Electron induced dissociation of glycosaminoglycan tetrasaccharides J Am Soc Mass Spectrom 19 1449 1458 18657442 10.1016/j.jasms.2008.06.024 1:CAS:528:DC%2BD1cXht1SntLnI
69. JJ Wolff TN Laremore AM Busch RJ Linhardt IJ Amster 2008 Influence of charge state and sodium cationization on the electron detachment dissociation and infrared multiphoton dissociation of glycosaminoglycan oligosaccharides J Am Soc Mass Spectrom 19 790 798 18499037 10.1016/j.jasms.2008.03.010 1:CAS:528:DC%2BD1cXmtlCjt7g%3D (Pubitemid 351680701)
70. JJ Wolff TN Laremore AM Busch RJ Linhardt IJ Amster 2008 Electron detachment dissociation of dermatan sulfate oligosaccharides J Am Soc Mass Spectrom 19 294 304 18055211 10.1016/j.jasms.2007.10.007 1:CAS:528: DC%2BD1cXitlyktbs%3D (Pubitemid 351249130)
71. J Zaia 2004 Mass spectrometry of oligosaccharides Mass Spectrom Rev 23 161 227 14966796 10.1002/mas.10073 1:CAS:528:DC%2BD2cXktVOmu7g%3D
72. J Zaia 2009 On-line separations combined with MS for analysis of glycosaminoglycans Mass Spectrom Rev 28 254 272 18956477 10.1002/mas.20200 1:CAS:528:DC%2BD1MXjs1KhtLc%3D
73. J Zaia CE Costello 2001 Compositional analysis of glycosaminoglycans by ESI MS Anal Chem 73 233 239 11199971 10.1021/ac000777a 1:CAS:528: DC%2BD3cXoslemu7g%3D (Pubitemid 32061834)
74. J Zaia JE McClellan CE Costello 2001 Tandem mass spectrometric determination of the 4S/6S sulfation sequence in chondroitin sulfate oligosaccharides Anal Chem 73 6030 6039 11791576 10.1021/ac015577t 1:CAS:528:DC%2BD3MXot1yhsLY%3D (Pubitemid 34042221)
75. J Zaia MJC Miller JL Seymour CE Costello 2007 The role of mobile protons in negative ion CID of oligosaccharides J Am Soc Mass Spectrom 18 952 960 17383193 10.1016/j.jasms.2007.01.016 1:CAS:528:DC%2BD2sXkvVWmtLo%3D (Pubitemid 46617286)
76. AD Zamfir J Peter-Katalinić 2004 Capillary electrophoresis-mass spectrometry for glycoscreening in biomedical research Electrophoresis 25 1949 1963 15237394 10.1002/elps.200405825 1:CAS:528:DC%2BD2cXmtFKlt74%3D (Pubitemid 39136314)
77. AD Zamfir D Seidler H Kresse J Peter-Katalinic 2002 Structural characterization of chondroitin/dermatan sulfate oligosaccharides from bovine aorta by capillary electrophoresis and electrospray ionization quadrupole time-of-flight tandem mass spectrometry Rapid Commun Mass Spectrom 16 2015 2024 12391574 10.1002/rcm.820 1:CAS:528:DC%2BD38XosF2lur8%3D (Pubitemid 35257108)
78. AD Zamfir D Seidler H Kresse J Peter-Katalinic 2003 Structural investigation of chondroitin/dermatan sulfate oligosaccharides from human skin fibroblast decorin Glycobiology 11 733 742 10.1093/glycob/cwg086 (Pubitemid 37407102)
79. AD Zamfir D Seidler E Schonherr H Kresse J Peter-Katalinić 2004 On-line sheathless capillary electrophoresis/nanoelectrospray ionization-tandem mass spectrometry for the analysis of glycosaminoglycan oligosaccharides Electrophoresis 25 2010 2016 15237401 10.1002/elps.200405925 1:CAS:528:DC%2BD2cXmtFKlt7k%3D (Pubitemid 39136321)
80. AD Zamfir C Flangea E Sisu AF Serb N Dinca P Bruckner DG Seidler 2009 Analysis of novel over- and under-sulfated glycosaminoglycan sequences by enzyme cleavage and multiple stage MS Proteomics 9 3435 3444 19557760 10.1002/pmic.200800440 1:CAS:528:DC%2BD1MXovVert70%3D
81. Y Zhang Y Kariya AH Conrad ES Tasheva GW Conrad 2005 Analysis of keratan sulfate oligosaccharides by electrospray ionization tandem mass spectrometry Anal Chem 77 902 910 15679360 10.1021/ac040074j 1:CAS:528:DC%2BD2MXjslCi (Pubitemid 40194155)
82. H Zhang T Muramatsu A Murase S Yuasa K Uchimura K Kadomatsu 2006 N-acetylglucosamine 6-O-sulfotransferase-1 is required for brain keratan sulfate biosynthesis and glial scar formation after brain injury Glycobiology 16 702 710 16624895 10.1093/glycob/cwj115 1:CAS:528:DC%2BD28XnvFWhtLg%3D (Pubitemid 44288236)
83. Z Zhang Y Park MM Kemp W Zhao AR Im D Shaya M Cygler YS Kim RJ Linhardt 2009 Liquid chromatography-mass spectrometry to study chondroitin lyase action pattern Anal Biochem 385 57 64 18992215 10.1016/j.ab.2008.10.014 1:CAS:528:DC%2BD1cXhsFCmsbzF
84. A Zinellu S Pisanu E Zinellu AJ Lepedda GM Cherchi S Sotgia C Carru L Deiana M Formato 2007 A novel LIF-CE method for the separation of hyaluronan- and chondroitin sulfate-derived disaccharides: Application to structural and quantitative analyses of human plasma low- and high-charged chondroitin sulfate isomers Electrophoresis 28 2439 2447 17577197 10.1002/elps.200600668 1:CAS:528:DC%2BD2sXos1Gjtbk%3D (Pubitemid 47162939)