Galectins as tools for glycan mapping in histology: Comparison of their binding profiles to the bovine zona pellucida by confocal laser scanning microscopy

Histochemistry and Cell Biology

Volumn 135, Issue 6, 2011, Pages 539-552

  Habermann, Felix A ^a   André, Sabine ^a   Kaltner, Herbert ^a   Kübler, Dieter ^b   Sinowatz, Fred ^a   Gabius, Hans Joachim ^a  

^a UNIVERSITY OF MUNICH   (Germany)

^b GERMAN CANCER RESEARCH CENTER DKFZ   (Germany)

Author keywords

Glycoprotein; Lectin; N Glycosylation; Sialylation; Zona pellucida

Indexed keywords

ECALECTIN; GALECTIN; GALECTIN 1; GALECTIN 2; GALECTIN 3; GALECTIN 4; GALECTIN 8; GLYCAN; GLYCINE MAX AGGLUTININ; LECTIN; LEUKOAGGLUTININ; PLANT LECTIN; SAMBUCUS NIGRA AGGLUTININ; SAMBUCUS NIGRA EXTRACT; TRITICUM VULGARE AGGLUTININ; UNCLASSIFIED DRUG; VISCUM ALBUM LECTIN;

ANIMAL CELL; ARTICLE; CONFOCAL LASER MICROSCOPY; CONTROLLED STUDY; COW; FUCOSYLATION; HISTOLOGY; NONHUMAN; OOCYTE; PRIORITY JOURNAL; PROTEIN ANALYSIS; PROTEIN BINDING; PROTEIN PHOSPHORYLATION; SIALYLATION; STAINING; ZONA PELLUCIDA;

ANIMALS; BINDING SITES; CATTLE; GALECTINS; MICROSCOPY, CONFOCAL; OOCYTES; PLANT LECTINS; POLYSACCHARIDES; ZONA PELLUCIDA;

BOVINAE; MAMMALIA;

EID: 79960243415     PISSN: 09486143     EISSN: 1432119X     Source Type: Journal    
DOI: 10.1007/s00418-011-0814-2     Document Type: Article

References (72)

1. N Ahmad HJ Gabius H Kaltner S André I Kuwabara FT Liu S Oscarson T Norberg CF Brewer 2002 Thermodynamic binding studies of cell surface carbohydrate epitopes to galectins-1, -3 and -7: evidence for differential binding specificities Can J Chem 80 1096 1104 10.1139/v02-162 1:CAS:528:DC%2BD38XnvFSlsbY%3D (Pubitemid 35370517)
2. N Ahmad HJ Gabius S André H Kaltner S Sabesan R Roy B Liu F Macaluso CF Brewer 2004 Galectin-3 precipitates as a pentamer with synthetic multivalent carbohydrates and forms heterogeneous cross-linked complexes J Biol Chem 279 10841 10847 14672941 10.1074/jbc.M312834200 1:CAS:528: DC%2BD2cXitFyit7k%3D (Pubitemid 38401573)
3. S Amari N Yonezawa S Mitsui T Katsumata S Hamano M Kuwayama Y Hashimoto A Suzuki Y Takeda M Nakano 2001 Essential role of the nonreducing terminal α-mannosyl residues of the N-linked carbohydrate chain of bovine zona pellucida glycoproteins in sperm-egg binding Mol Reprod Dev 59 221 226 11389558 10.1002/mrd.1026 1:CAS:528:DC%2BD3MXjsValsL8%3D (Pubitemid 32391249)
4. S André H Kaltner M Lensch R Russwurm HC Siebert C Fallsehr E Tajkhorshid AJ Heck M von Knebel Doeberitz HJ Gabius J Kopitz 2005 Determination of structural and functional overlap/divergence of five proto-type galectins by analysis of the growth-regulatory interaction with ganglioside GM1 in silico and in vitro on human neuroblastoma cells Int J Cancer 114 46 57 15523676 10.1002/ijc.20699 (Pubitemid 40194308)
5. S André Z Pei HC Siebert O Ramström HJ Gabius 2006 Glycosyldisulfides from dynamic combinatorial libraries as O-glycoside mimetics for plant and endogenous lectins: their reactivities in solid-phase and cell assays and conformational analysis by molecular dynamics simulations Bioorg Med Chem 14 6314 6326 16782346 10.1016/j.bmc.2006.05.045 (Pubitemid 44224074)
6. INK4a: modulator of glycomic profile and galectin-1 expression to increase susceptibility to carbohydrate-dependent induction of anoikis in pancreatic carcinoma cells FEBS J 274 3233 3256 17535296 10.1111/j.1742-4658. 2007.05851.x (Pubitemid 47028461)
7. S André F Sansone H Kaltner A Casnati J Kopitz HJ Gabius R Ungaro 2008 Calix[n]arene-based glycoclusters: bioactivity of thiourea-linked galactose/lactose moieties as inhibitors of binding of medically relevant lectins to a glycoprotein and cell-surface glycoconjugates and selectivity among human adhesion/growth-regulatory galectins ChemBioChem 9 1649 1661 18509838 10.1002/cbic.200800035
8. S André T Kožár S Kojima C Unverzagt HJ Gabius 2009 From structural to functional glycomics: core substitutions as molecular switches for shape and lectin affinity of N-glycans Biol Chem 390 557 565 19426132 10.1515/BC.2009.072
9. Buddecke E (2009) Proteoglycans. In: Gabius HJ (ed) The sugar code. Fundamentals of glycosciences. Wiley-VCH, Weinheim, pp 199-216
10. HA Chokhawala S Huang K Lau H Yu J Cheng V Thon N Hurtado-Ziola JA Guerrero A Varki X Chen 2008 Combinatorial chemoenzymatic synthesis and high-throughput screening of sialosides ACS Chem Biol 3 567 576 18729452 10.1021/cb800127n 1:CAS:528:DC%2BD1cXhtVGgurvM
11. DNW Cooper 2002 Galectinomics: finding themes in complexity Biochim Biophys Acta 1572 209 231 12223271 1:CAS:528:DC%2BD38XmvVagsL4%3D (Pubitemid 35246346)
12. TK Dam HJ Gabius S André H Kaltner M Lensch CF Brewer 2005 Galectins bind to the multivalent glycoprotein asialofetuin with enhanced affinities and a gradient of decreasing binding constants Biochemistry 44 12564 12571 16156668 10.1021/bi051144z 1:CAS:528:DC%2BD2MXovFWht7o%3D (Pubitemid 41324347)
13. N Diéz-Revuelta S Velasco S André H Kaltner D Kübler HJ Gabius J Abad-Rodríguez 2010 Phosphorylation of adhesion- and growth-regulatory human galectin-3 leads to the induction of axonal branching by local membrane L1 and ERM redistribution J Cell Sci 123 671 681 20124415 10.1242/jcs.058198
14. RL Easton MS Patankar FA Lattanzio TH Leaven HR Morris GF Clark A Dell 2000 Structural analysis of murine zona pellucida glycans J Biol Chem 275 7731 7742 10713085 10.1074/jbc.275.11.7731 1:CAS:528:DC%2BD3cXitVylsLo%3D (Pubitemid 30159677)
15. HJ Gabius 2006 Cell surface glycans: the why and how of their functionality as biochemical signals in lectin-mediated information transfer Crit Rev Immunol 26 43 79 16472068 1:CAS:528:DC%2BD28XitVWks7Y%3D
16. Gabius HJ (ed) (2009) The sugar code. Fundamentals of glycosciences. Wiley-VCH, Weinheim
17. HJ Gabius 2011 Glycobiomarkers by glycoproteomics and glycan profiling (glycomics): emergence of functionality Biochem Soc Trans 39 399 405 21265812 10.1042/BST0390399 1:CAS:528:DC%2BC3MXhsVShtrc%3D
18. HJ Gabius R Engelhardt F Cramer R Bätge GA Nagel 1985 Pattern of endogenous lectins in a human epithelial tumor Cancer Res 45 253 257 3965138 1:CAS:528:DyaL2MXmtVWqsg%3D%3D (Pubitemid 15196964)
19. HJ Gabius B Wosgien M Hendrys A Bardosi 1991 Lectin localization in human nerve by biochemically defined lectin-binding glycoproteins, neoglycoprotein and lectin-specific antibody Histochemistry 95 269 277 2050547 10.1007/BF00266777 1:CAS:528:DyaK3MXhvVWmsLY%3D
20. HJ Gabius H Walzel SS Joshi J Kruip S Kojima V Gerke H Kratzin S Gabius 1992 The immunomodulatory β-galactoside-specific lectin from mistletoe: partial sequence analysis, cell and tissue binding, and impact on intracellular biosignalling of monocytic leukemia cells Anticancer Res 12 669 675 1622124 1:CAS:528:DyaK3sXhsF2qsA%3D%3D
21. OE Galanina H Kaltner LS Khraltsova NV Bovin HJ Gabius 1997 Further refinement of the description of the ligand-binding characteristics for the galactoside-binding mistletoe lectin, a plant agglutinin with immunomodulatory potency J Mol Recognit 10 139 147 9408830 10.1002/(SICI)1099-1352(199705/06)10: 3<139::AID-JMR358>3.0.CO;2-R 1:CAS:528:DyaK2sXnvFaksrk%3D (Pubitemid 28012387)
22. A Göhler S André H Kaltner M Sauer HJ Gabius S Doose 2010 Hydrodynamic properties of human adhesion/growth-regulatory galectins studied by fluorescence correlation spectroscopy Biophys J 98 3044 3053 20550917 10.1016/j.bpj.2010.03.040
23. Habermann FA, Sinowatz F (2009) Glycobiology and early embryonic development. In: Gabius HJ (ed) The sugar code. Fundamentals of glycosciences. Wiley-VCH, Weinheim, pp 403-417
24. J Hirabayashi T Hashidate Y Arata N Nishi T Nakamura M Hirashima T Urashima T Oka M Futai WEG Müller F Yagi K-i Kasai 2002 Oligosaccharide specificity of galectins: a search by frontal affinity chromatography Biochim Biophys Acta 1572 232 254 12223272 1:CAS:528:DC%2BD38XmvVagsLw%3D (Pubitemid 35246347)
25. H Ideo A Seko I Ishizuka K Yamashita 2003 The N-terminal carbohydrate recognition domain of galectin-8 recognizes specific glycosphingolipids with high affinity Glycobiology 13 713 723 12851289 10.1093/glycob/cwg094 1:CAS:528:DC%2BD3sXnsVeksbc%3D (Pubitemid 37337052)
26. K Ikeda N Yonezawa K Naoi T Katsumata S Hamano M Nakano 2002 Localization of N-linked carbohydrate chains in glycoprotein ZPA of the bovine egg zona pellucida Eur J Biochem 269 4257 4266 12199704 10.1046/j.1432-1033.2002.03111.x 1:CAS:528:DC%2BD38Xnt1eiurs%3D (Pubitemid 35026012)
27. DH Joziasse WECM Schiphorst DH van den Eijnden JA van Kuik H van Halbeek JFG Vliegenthart 1987 Branch specificity of bovine colostrum CMP-sialic acid: Galβ1 → 4GlcNAc-R α2 → 6-sialyltransferase. Sialylation of bi-, tri-, and tetraantennary oligosaccharides and glycopeptides of the N-acetyllactosamine type J Biol Chem 262 2025 2033 3546284 1:CAS:528: DyaL2sXktlGmsb4%3D
28. H Kaltner D Solís J Kopitz M Lensch M Lohr JC Manning M Mürnseer M Schnölzer S André JL Sáiz HJ Gabius 2008 Prototype chicken galectins revisited: characterization of a third protein with distinctive hydrodynamic behaviour and expression pattern in organs of adult animals Biochem J 409 591 599 17887955 10.1042/BJ20070419 1:CAS:528: DC%2BD1cXhtlSru7s%3D (Pubitemid 351184978)
29. H Kaltner D Kübler L López-Merino M Lohr JC Maninng M Lensch J Seidler WD Lehmann S André D Solís HJ Gabius 2011 Toward comprehensive analysis of the galectin network in chicken: unique diversity of galectin-3 and comparison of its localization profile in organs of adult animals to the other four members of this lectin family Anat Rec 294 427 444 10.1002/ar.21341 1:CAS:528:DC%2BC3MXktlyltrc%3D
30. T Katsumata S Noguchi N Yonezawa M Tanokura M Nakano 1996 Structural characterization of the N-linked carbohydrate chains of the zona pellucida glycoproteins from bovine ovarian and fertilized eggs Eur J Biochem 240 448 453 8841411 10.1111/j.1432-1033.1996.0448h.x 1:CAS:528:DyaK28XlsF2gtL8%3D (Pubitemid 26292754)
31. DC Kilpatrick C Green 1992 Lectins as blood typing reagents Adv Lectin Res 5 51 94 1:CAS:528:DyaK2cXkvVSgtb8%3D
32. a antigen is the predominant N-glycan on bovine pregnancy-associated glycoproteins Glycobiology 18 42 52 17951374 10.1093/glycob/cwm113 1:CAS:528:DC%2BD1cXhtFeisw%3D%3D
33. RN Knibbs IJ Goldstein RM Ratcliffe N Shibuya 1991 Characterization of the carbohydrate binding specificity of the leukoagglutinating lectin from Maackia amurensis. Comparison with other sialic acid-specific lectins J Biol Chem 266 83 88 1985926 1:CAS:528:DyaK3MXhvVSmur4%3D (Pubitemid 21906093)
34. Kopitz J (2009) Glycolipids. In: Gabius HJ (ed) The sugar code. Fundamentals of glycosciences. Wiley-VCH, Weinheim, pp 177-198
35. J Kopitz C von Reitzenstein S André H Kaltner J Uhl V Ehemann M Cantz HJ Gabius 2001 Negative regulation of neuroblastoma cell growth by carbohydrate-dependent surface binding of galectin-1 and functional divergence from galectin-3 J Biol Chem 276 35917 35923 11451961 10.1074/jbc.M105135200 1:CAS:528:DC%2BD3MXntFahtL4%3D
36. J Kopitz M Bergmann HJ Gabius 2010 How adhesion/growth-regulatory galectins-1 and -3 attain cell specificity: case study defining their target on neuroblastoma cells (SK-N-MC) and marked affinity regulation by affecting microdomain organization of the membrane IUBMB Life 62 624 628 20665623 10.1002/iub.358 1:CAS:528:DC%2BC3cXpsF2rsrs%3D
37. M Krzeminski T Singh S André M Lensch AM Wu AMJJ Bonvin HJ Gabius 2011 Human galectin-3 (Mac-2 antigen): defining molecular switches of affinity to natural glycoproteins, structural and dynamic aspects of glycan binding by flexible ligand docking and putative regulatory sequences in the proximal promoter region Biochim Biophys Acta 1810 150 161 21070836 1:CAS:528: DC%2BC3cXhs1ajsL7O
38. D Kübler CW Hung TK Dam J Kopitz S André H Kaltner M Lohr JC Manning L He H Wang A Middelberg CF Brewer J Reed WD Lehmann HJ Gabius 2008 Phosphorylated human galectin-3: facile large-scale preparation of active lectin and detection of structural changes by CD spectroscopy Biochim Biophys Acta 1780 716 722 18302943
39. L Leibfried NL First 1979 Characterization of bovine follicular oocytes and their ability to mature in vitro J Anim Sci 48 76 86 573253 1:STN:280:DyaL3c%2Fgs1arsA%3D%3D
40. R Leyden T Velasco-Torrijos S André S Gouin HJ Gabius PV Murphy 2009 Synthesis of bivalent lactosides based on terephthalamide, N, N′-diglucosylterephthalamide, and glycophane scaffolds and assessment of their inhibitory capacity on medically relevant lectins J Org Chem 74 9010 9026 19899775 10.1021/jo901667r 1:CAS:528:DC%2BD1MXhtlyrsLfM
41. M Lohr H Kaltner M Lensch S André F Sinowatz HJ Gabius 2008 Cell-type-specific expression of murine multifunctional galectin-3 and its association with follicular atresia/luteolysis in contrast to pro-apoptotic galectins-1 and -7 Histochem Cell Biol 130 567 581 18597104 10.1007/s00418-008- 0465-0 1:CAS:528:DC%2BD1cXhtVWns7nO
42. M Lohr H Kaltner R Schwartz-Albiez F Sinowatz HJ Gabius 2010 Towards functional glycomics by lectin histochemistry: strategic probe selection to monitor core and branch-end substitutions and detection of cell-type and regional selectivity in adult mouse testis and epididymis Anat Histol Embryol 39 481 493 20624157 10.1111/j.1439-0264.2010.01019.x 1:STN:280: DC%2BC3cbntlOruw%3D%3D
43. M Monsigny AC Roche C Sene R Maget-Dana F Delmotte 1980 Sugar-lectin interactions: how does wheat-germ agglutinin bind sialoglycoconjugates? Eur J Biochem 104 147 153 6892800 10.1111/j.1432-1033.1980.tb04410.x 1:CAS:528:DyaL3cXhslyqsrg%3D
44. W Morelle L Stechly S André I van Seuningen N Porchet HJ Gabius JC Michalski G Huet 2009 Glycosylation pattern of brush border-associated glycoproteins in enterocyte-like cells: involvement of complex-type N-glycans in apical trafficking Biol Chem 390 529 544 19426135 10.1515/BC.2009.075 1:CAS:528:DC%2BD1MXotlGjt7g%3D
45. N Nishi A Itoh A Fujiyama N Yoshida S Araya M Hirashima H Shoji T Nakamura 2005 Development of highly stable galectins: truncation of the linker peptide confers protease-resistance on tandem-repeat type galectins FEBS Lett 579 2058 2064 15811318 10.1016/j.febslet.2005.02.054 1:CAS:528: DC%2BD2MXjtlWis7g%3D (Pubitemid 40469670)
46. Patsos G, Corfield A (2009) O-Glycosylation: structural diversity and functions. In: Gabius HJ (ed) The sugar code. Fundamentals of glycosciences. Wiley-VCH, Weinheim, pp 111-137
47. G Patsos S André N Roeckel R Gromes J Gebert J Kopitz HJ Gabius 2009 Compensation of loss of protein function in microsatellite-unstable colon cancer cells (HCT116): a gene-dependent effect on the cell surface glycan profile Glycobiology 19 726 734 19293232 10.1093/glycob/cwp040 1:CAS:528:DC%2BD1MXms1Cjtr8%3D
48. EM Rapoport S André OV Kurmyshkina TV Pochechueva VV Severov GV Pazynina HJ Gabius NV Bovin 2008 Galectin-loaded cells as a platform for the profiling of lectin specificity by fluorescent neoglycoconjugates: a case study on galectins-1 and -3 and the impact of assay setting Glycobiology 18 315 324 18256179 10.1093/glycob/cwn009 1:CAS:528:DC%2BD1cXltlektrc%3D (Pubitemid 351461064)
49. J Roth 1996 Protein glycosylation in the endoplasmic reticulum and the Golgi apparatus and cell type-specificity of cell surface glycoconjugate expression: analysis by the protein A-gold and lectin-gold techniques Histochem Cell Biol 106 79 92 8858368 10.1007/BF02473203 1:CAS:528:DyaK28XkslCgt7k%3D (Pubitemid 26291494)
50. H Rüdiger HJ Gabius 2001 Plant lectins: occurrence, biochemistry, functions and applications Glycoconj J 18 589 613 12376725 10.1023/A: 1020687518999 (Pubitemid 35341855)
51. Rüdiger H, Gabius HJ (2009) Plant lectins. In: Gabius HJ (ed) The sugar code. Fundamentals of glycosciences. Wiley-VCH, Weinheim, pp 301-315
52. I Saal N Nagy M Lensch M Lohr JC Manning C Decaestecker S André R Kiss I Salmon HJ Gabius 2005 Human galectin-2: expression profiling by RT-PCR/immunohistochemistry and its introduction as a histochemical tool for ligand localization Histol Histopathol 20 1191 1208 16136502 1:CAS:528:DC%2BD2MXht1OksLjN (Pubitemid 41489164)
53. INK4a: downregulation of galectin-3, an endogenous competitor of the pro-anoikis effector galectin-1, in a pancreatic carcinoma model FEBS J 277 3552 3563 20695889 10.1111/j.1742-4658.2010.07764.x 1:CAS:528:DC%2BC3cXhtFWmsb%2FE
54. K Sarter S André H Kaltner M Lensch C Schulze V Urbonaviciute G Schett M Herrmann HJ Gabius 2009 Detection and chromatographic removal of lipopolysaccharide in preparations of multifunctional galectins Biochem Biophys Res Commun 379 155 159 19101505 10.1016/j.bbrc.2008.12.024 1:CAS:528: DC%2BD1MXosVSiug%3D%3D
55. S Saussez C Decaestecker F Lorfevre D Chevalier G Mortuaire H Kaltner S André G Toubeau HJ Gabius X Leroy 2008 Increased expression and altered intracellular distribution of adhesion/growth-regulatory lectins galectins-1 and -7 during tumour progression in hypopharyngeal and laryngeal squamous cell carcinomas Histopathology 52 483 493 18315601 10.1111/j.1365-2559.2008.02973.x 1:STN:280:DC%2BD1c7lslGgsA%3D%3D (Pubitemid 351327984)
56. Schwartz-Albiez R (2009) Inflammation and glycosciences. In: Gabius HJ (ed) The sugar code. Fundamentals of glycosciences. Wiley-VCH, Weinheim, pp 447-467
57. A Schwarz AH Futerman 1997 Determination of the localization of gangliosides using anti-ganglioside antibodies: comparison of fixation methods J Histochem Cytochem 45 611 618 9111239 10.1177/002215549704500413 1:CAS:528:DyaK2sXislamtL8%3D (Pubitemid 27175805)
58. F Sinowatz E Töpfer-Petersen S Kölle G Palma 2001 Functional morphology of the zona pellucida Anat Histol Embryol 30 257 263 11688734 10.1046/j.1439-0264.2001.00337.x 1:STN:280:DC%2BD3Mnjs1Wnuw%3D%3D (Pubitemid 32943924)
59. K Smetana Jr B Dvořánková M Chovanec J Bouček J Klíma J Motlík M Lensch H Kaltner S André HJ Gabius 2006 Nuclear presence of adhesion/growth-regulatory galectins in normal/malignant cells of squamous epithelial origin Histochem Cell Biol 125 171 182 16261331 10.1007/s00418-005-0074-0 1:CAS:528:DC%2BD28XhvF2hsw%3D%3D (Pubitemid 43049983)
60. D Solís MJ Maté M Lohr JP Ribeiro L López-Merino S André E Buzamet FJ Cañada H Kaltner M Lensch FM Ruiz G Haroske U Wollina M Kloor J Kopitz JL Sáiz M Menéndez J Jiménez- Barbero A Romero HJ Gabius 2010 N-Domain of human adhesion/growth-regulatory galectin-9: preference for distinct conformers and non-sialylated N-glycans and detection of ligand-induced structural changes in crystal and solution Int J Biochem Cell Biol 42 1019 1029 20227520 10.1016/j.biocel.2010.03.007
61. CP Sparrow H Leffler SH Barondes 1987 Multiple soluble β-galactoside-binding lectins from human lung J Biol Chem 262 7383 7390 2438278 1:CAS:528:DyaL2sXksFKhurk%3D
62. L Stechly W Morelle AF Dessein S André G Grard D Trinel MJ Dejonghe E Leteurtre H Drobecq G Trugnan HJ Gabius G Huet 2009 Galectin-4-regulated delivery of glycoproteins to the brush border membrane of enterocyte-like cells Traffic 10 438 450 19192249 10.1111/j.1600-0854.2009. 00882.x 1:CAS:528:DC%2BD1MXnt1Clsrs%3D
63. SR Stowell CM Arthur KA Slanina JR Horton DF Smith RD Cummings 2008 Dimeric galectin-8 induces phosphatidylserine exposure in leukocytes through polylactosamine recognition by the C-terminal domain J Biol Chem 283 20547 20559 18456665 10.1074/jbc.M802495200 1:CAS:528:DC%2BD1cXotlOhs70%3D
64. P Szabo TK Dam K Smetana Jr B Dvořánková D Kübler CF Brewer HJ Gabius 2009 Phosphorylated human lectin galectin-3: analysis of ligand binding by histochemical monitoring of normal/malignant squamous epithelia and by isothermal titration calorimetry Anat Histol Embryol 38 68 75 18983621 10.1111/j.1439-0264.2008.00899.x 1:STN:280: DC%2BD1M%2FntVOmsQ%3D%3D
65. R Talevi R Gualtieri G Tartaglione A Fortunato 1997 Heterogeneity of the zona pellucida carbohydrate distribution in human oocytes failing to fertilize in vitro Hum Reprod 12 2773 2780 9455851 10.1093/humrep/12.12.2773 1:CAS:528:DyaK1cXmsVOhuw%3D%3D (Pubitemid 28031746)
66. C Unverzagt S André J Seifert S Kojima C Fink G Srikrishna H Freeze K Kayser HJ Gabius 2002 Structure-activity profiles of complex biantennary glycans with core fucosylation and with/without additional α2,3/α2,6 sialylation: synthesis of neoglycoproteins and their properties in lectin assays, cell binding, and organ uptake J Med Chem 45 478 491 11784152 10.1021/jm0110237 1:CAS:528:DC%2BD3MXptFyjtLw%3D (Pubitemid 34073465)
67. van den Eijnden DH (2000) On the origin of oligosaccharide species: glycosyltransferases in action. In: Ernst B, Hart GW, Sinaÿ P (eds) Carbohydrates in chemistry and biology. Wiley-VCH, Weinheim, pp 589-624
68. JG Velásquez S Canovas P Barajas J Marcos M Jiménez-Movilla RG Gallego J Ballesta M Avilés P Coy 2007 Role of sialic acid in bovine sperm-zona pellucida binding Mol Reprod Dev 74 617 628 17044044 10.1002/mrd.20619 (Pubitemid 46493751)
69. A Villalobo A Nogales-González HJ Gabius 2006 A guide to signalling pathways connecting protein-glycan interaction with the emerging versatile effector functionality of mammalian lectins Trends Glycosci Glycotechnol 18 1 37 1:CAS:528:DC%2BD28XltlKns7c%3D (Pubitemid 43723385)
70. J Wang ZH Lu HJ Gabius C Rohowsky-Kochan RW Ledeen G Wu 2009 Cross-linking of GM1 ganglioside by galectin-1 mediates regulatory T cell activity involving TRPC5 channel activation: possible role in suppressing experimental autoimmune encephalomyelitis J Immunol 182 4036 4045 19299701 10.4049/jimmunol.0802981 1:CAS:528:DC%2BD1MXjsVSjt7g%3D
71. AM Wu T Singh JH Liu M Krzeminski R Russwurm HC Siebert AMJJ Bonvin S André HJ Gabius 2007 Activity-structure correlations in divergent lectin evolution: fine specificity of chicken galectin CG-14 and computational analysis of flexible ligand docking for CG-14 and the closely related CG-16 Glycobiology 17 165 184 17060369 10.1093/glycob/cwl062 1:CAS:528:DC%2BD2sXotFGksg%3D%3D (Pubitemid 46152534)
72. Zuber C, Roth J (2009) N-Glycosylation. In: Gabius HJ (ed) The sugar code. Fundamentals of glycosciences. Wiley-VCH, Weinheim, pp 87-110