Application of carbohydrate array technology to antigen discovery and vaccine development

Expert Review of Vaccines

Volumn 6, Issue 6, 2007, Pages 957-969

  Oyelaran, Oyindasola ^a   Gildersleeve, Jeffrey C ^a  

^a NATIONAL CANCER INSTITUTE   (United States)

Author keywords

Antibodies; Antigen arrays; Cancer vaccines; Carbohydrates; Glycans; Glycoconjugates; Microarrays; Polysaccharide vaccines; Post translational modifications

Indexed keywords

ACT HIB; ANTIGEN; CARBOHYDRATE; EXOTOXIN; GANGLIOSIDE GM2; GMK; HAEMOPHILUS INFLUENZAE TYPE B HEPATITIS B VACCINE; HAEMOPHILUS INFLUENZAE TYPE B VACCINE; HIB TITER; MENINGOCOCCUS VACCINE; MENOMMUNE; PEDVAX; PNEUMOCOCCUS VACCINE; POLYSIALIC ACID; RECOMBINANT EXOTOXIN A VI; SHIGELLA VACCINE; THERATOPA; THERATOPE; TYPHOID VACCINE; UNCLASSIFIED DRUG; VACCINE;

DRUG DEVELOPMENT; FOOD AND DRUG ADMINISTRATION; HUMAN; IMMUNE RESPONSE; PRIORITY JOURNAL; REVIEW;

ANIMALS; CARBOHYDRATES; CLINICAL TRIALS AS TOPIC; HUMANS; MICROARRAY ANALYSIS; TECHNOLOGY, PHARMACEUTICAL; VACCINES;

EID: 37149047055     PISSN: 14760584     EISSN: 17448395     Source Type: Journal    
DOI: 10.1586/14760584.6.6.957     Document Type: Review

References (104)

1. Galili U, Rachmilewitz EA, Peleg A, Flechner I. A unique natural human IgG antibody with anti-α-galactosyl specificity. J. Exp. Med. 160(5), 1519-1531 (1984).
2. Galili U, Macher BA, Buehler J, Shohet SB. Human natural anti-α-galactosyl IgG. II. The specific recognition of α (1-3)-linked galactose residues. J. Exp. Med. 162(2), 573-582 (1985).
3. Galili U, Clark MR, Shohet SB, Buehler J, Macher BA. Evolutionary relationship between the natural anti-Gal antibody and the Gal-α(1-3)-Gal epitope in primates. Proc. Natl Acad. Sci. USA 84(5), 1369-1373 (1987).
4. Chen X, Andreana PR, Wang PG. Carbohydrates in transplantation. Curr. Opin. Chem. Biol. 3(6), 650-658 (1999).
5. Sandrin MS, Vaughan HA, Dabkowski PL, McKenzie IF. Anti-pig IgM antibodies in human serum react predominantly with Gal(α 1-3)Gal epitopes. Proc. Natl Acad. Sci. USA 90(23), 11391-11395 (1993).
6. Vliegenthart JF. Carbohydrate based vaccines. FEBS Lett. 580(12), 2945-2950 (2006).
7. Roy R. New trends in carbohydrate-based vaccines. Drug Discov. Today Technol. 1(3), 327-336 (2004).
8. Lucas AH, Apicella MA, Taylor CE. Carbohydrate moieties as vaccine candidates. Clin. Infect. Dis. 41(5), 705-712 (2005).
9. Haemophilus influenzae type b. In: Centers for Disease Control and Prevention. Epidemiology and Prevention of Vaccine-Preventable Diseases. Atkinson W, Hamborsky J, McIntyre L, Wolfe S (Eds). Public Health Foundation, Washington, DC, USA 115-128 (2007).
10. Pneumococcal disease. In: Centers for Disease Control and Prevention. Epidemiology and Prevention of Vaccine-Preventable Diseases. Atkinson W, Hamborsky J, McIntyre L, Wolfe S (Eds). Public Health Foundation, Washington, DC, USA 257-270 (2007).
11. Seeberger PH, Soucy RL, Kwon YU, Snyder DA, Kanemitsu T. A convergent, versatile route to two synthetic conjugate anti-toxin malaria vaccines. Chem. Commun. (Camb.) 15, 1706-1707 (2004).
12. Schofield L, Hewitt MC, Evans K, Siomos MA, Seeberger PH. Synthetic GPI as a candidate anti-toxic vaccine in a model of malaria. Nature 418(6899), 785-789 (2002).
13. Boutonnier A, Villeneuve S, Nato F, Dassy B, Fournier JM. Preparation, immunogenicity, and protective efficacy, in a murine model, of a conjugate vaccine composed of the polysaccharide moiety of the lipopolysaccharide of Vibrio cholerae O139 bound to tetanus toxoid. Infect. Immun. 69(5), 3488-3493 (2001).
14. Chowers Y, Kirschner J, Keller N et al. O-specific [corrected] polysaccharide conjugate vaccine-induced [corrected] antibodies prevent invasion of Shigella into Caco-2 cells and may be curative. Proc. Natl Acad. Sci. USA 104(7), 2396-2401 (2007).
15. Sabharwal H, Michon F, Nelson D et al. Group A streptococcus (GAS) carbohydrate as an immunogen for protection against GAS infection. J. Infect. Dis. 193(1), 129-135 (2006).
16. Baker CJ, Edwards MS. Group B streptococcal conjugate vaccines. Arch. Dis. Child. 88(5), 375-378 (2003).
17. Heath PT, Feldman RG. Vaccination against group B streptococcus. Expert Rev. Vaccines 4(2), 207-218 (2005).
18. Hewitt MC, Seeberger PH. Solution and solid-support synthesis of a potential leishmaniasis carbohydrate vaccine. J. Org. Chem. 66(12), 4233-4243 (2001).
19. Liu X, Siegrist S, Amacker M, Zurbriggen R, Pluschke G, Seeberger PH. Enhancement of the immunogenicity of synthetic carbohydrates by conjugation to virosomes: a leishmaniasis vaccine candidate. ACS Chem. Biol. 1(3), 161-164 (2006).
20. Werz DB, Seeberger PH. Total synthesis of antigen bacillus anthracis tetrasaccharide - creation of an anthrax vaccine candidate. Angew. Chem. Int. Ed. Engl. 44(39), 6315-6318 (2005).
21. Wang LX, Ni J, Singh S, Li H. Binding of high-mannose-type oligosaccharides and synthetic oligomannose clusters to human antibody 2G12: implications for HIV-1 vaccine design. Chem. Biol. 11(1), 127-134 (2004).
22. Li H, Wang LX. Design and synthesis of a template-assembled oligomannose cluster as an epitope mimic for human HIV-neutralizing antibody 2G12. Org. Biomol. Chem. 2(4), 483-488 (2004).
23. Cutler JE. Defining criteria for anti-mannan antibodies to protect against candidiasis. Curr. Mol. Med. 5(4), 383-392 (2005).
24. Han Y, Ulrich MA, Cutler JE. Candida albicans mannan extract-protein conjugates induce a protective immune response against experimental candidiasis. J. Infect. Dis. 179(6), 1477-1484 (1999).
25. Bystricky S, Paulovicova E, Machova E. Candida albicans mannan-protein conjugate as vaccine candidate. Immunol. Lett. 85(3), 251-255 (2003).
26. Livingston PO, Wong GY, Adluri S et al. Improved survival in stage III melanoma patients with GM2 antibodies: a randomized trial of adjuvant vaccination with GM2 ganglioside. J. Clin. Oncol. 12(5), 1036-1044 (1994).
27. Tai T, Cahan LD, Tsuchida T, Saxton RE, Irie RF, Morton DL. Immunogenicity of melanoma-associated gangliosides in cancer patients. Int. J. Cancer 35(5), 607-612 (1985).
28. Tai T, Paulson JC, Cahan LD, Irie RF. Ganglioside GM2 as a human tumor antigen (OFA-I-1). Proc. Natl Acad. Sci. USA 80(17), 5392-5396 (1983).
29. Helling F, Zhang S, Shang A et al. GM2-KLH conjugate vaccine: increased immunogenicity in melanoma patients after administration with immunological adjuvant QS-21. Cancer Res. 55(13), 2783-2788 (1995).
30. Chapman PB, Morrissey DM, Panageas KS et al. Induction of antibodies against GM2 ganglioside by immunizing melanoma patients using GM2-keyhole limpet hemocyanin + QS21 vaccine: a dose-response study. Clin. Cancer Res. 6(3), 874-879 (2000).
31. Lo-Man R, Vichier-Guerre S, Perraut R et al. A fully synthetic therapeutic vaccine candidate targeting carcinoma-associated Tn carbohydrate antigen induces tumor-specific antibodies in nonhuman primates. Cancer Res. 64(14), 4987-4994 (2004).
32. Slovin SF, Ragupathi G, Musselli C et al. Thomsen-Friedenreich (TF) antigen as a target for prostate cancer vaccine: clinical trial results with TF cluster (c)-KLH plus QS21 conjugate vaccine in patients with biochemically relapsed prostate cancer. Cancer Immunol. Immunother. 54(7), 694-702 (2005).
33. Gilewski TA, Ragupathi G, Dickler M et al. Immunization of high-risk breast cancer patients with clustered sTn-KLH conjugate plus the immunologic adjuvant QS-21. Clin. Cancer Res. 13(10), 2977-2985 (2007).
34. Sabbatini PJ, Kudryashov V, Ragupathi G et al. Immunization of ovarian cancer patients with a synthetic Lewis(y)-protein conjugate vaccine: a Phase 1 trial. Int. J. Cancer 87(1), 79-85 (2000).
35. Ragupathi G, Koide F, Sathyan N et al. A preclinical study comparing approaches for augmenting the immunogenicity of a heptavalent KLH-conjugate vaccine against epithelial cancers. Cancer Immunol. Immunother. 52(10), 608-616 (2003).
36. Krug LM, Ragupathi G, Ng KK et al. Vaccination of small cell lung cancer patients with polysialic acid or N-propionylated polysialic acid conjugated to keyhole limpet hemocyanin. Clin. Cancer Res. 10(3), 916-923 (2004).
37. Wang ZG, Williams LJ, Zhang XF et al. Polyclonal antibodies from patients immunized with a Globo H-keyhole limpet hemocyanin vaccine: isolation, quantification, and characterization of immune responses by using totally synthetic immobilized tumor antigens. Proc. Natl Acad. Sci. USA 97(6), 2719-2724 (2000).
38. Gilewski T, Ragupathi G, Bhuta S et al. Immunization of metastatic breast cancer patients with a fully synthetic Globo H conjugate: a Phase I trial. Proc. Natl Acad. Sci. USA 98(6), 3270-3275 (2001).
39. Ouerfelli O, Warren JD, Wilson RM, Danishefsky SJ. Synthetic carbohydrate-based antitumor vaccines: challenges and opportunities. Expert Rev. Vaccines 4(5), 677-685 (2005).
40. Kaltgrad E, Sen Gupta S, Punna S et al. Anti-carbohydrate antibodies elicited by polyvalent display on a viral scaffold. Chembiochem 8(12), 1455-1462 (2007).
41. Feizi T, Chai W. Oligosaccharide microarrays to decipher the glyco code. Nat. Rev. Mol. Cell Biol. 5(7), 582-588 (2004).
42. Shin I, Park S, Lee MR. Carbohydrate microarrays: an advanced technology for functional studies of glycans. Chemistry 11(10), 2894-2901 (2005).
43. Paulson JC, Blixt O, Collins BE. Sweet spots in functional glycomics. Nat. Chem. Biol. 2(5), 238-248 (2006).
44. Dyukova VI, Shilova NV, Galanina OE, Rubina AY, Bovin NV. Design of carbohydrate multiarrays. Biochim. Biophys. Acta 1760(4), 603-609 (2006).
45. Wang D, Liu S, Trummer BJ, Deng C, Wang A. Carbohydrate microarrays for the recognition of cross-reactive molecular markers of microbes and host cells. Nat. Biotechnol. 20(3), 275-281 (2002).
46. Willats WG, Rasmussen SE, Kristensen T, Mikkelsen JD, Knox JP. Sugar-coated microarrays: a novel slide surface for the high-throughput analysis of glycans. Proteomics 2(12), 1666-1671 (2002).
47. Fukui S, Feizi T, Galustian C, Lawson AM, Chai W. Oligosaccharide microarrays for high-throughput detection and specificity assignments of carbohydrate-protein interactions. Nat. Biotechnol. 20(10), 1011-1017 (2002).
48. Bryan MC, Plettenburg O, Sears P, Rabuka D, Wacowich-Sgarbi S, Wong CH. Saccharide display on microtiter plates. Chem. Biol. 9(6), 713-720 (2002).
49. Bryan MC, Fazio F, Lee HK et al. Covalent display of oligosaccharide arrays in microtiter plates. J. Am. Chem. Soc. 126(28), 8640-8641 (2004).
50. Huang GL, Zhang HC, Wang PG. Fabrication and application of neoglycolipid arrays in a microtiter plate. Bioorg. Med. Chem. Lett. 16(7), 2031-2033 (2006).
51. Fazio F, Bryan MC, Lee HK, Chang A, Wong CH. Assembly of sugars on polystyrene plates: a new facile microarray fabrication technique. Tetrahedron Lett. 45(12), 2689-2692 (2004).
52. Ko KS, Jaipuri FA, Pohl NL. Fluorous-based carbohydrate microarrays. J. Am. Chem. Soc. 127(38), 13162-13163 (2005).
53. Mamidyala SK, Ko KS, Jaipuri FA, Park G, Pohl NL. Noncovalent fluorous interactions for the synthesis of carbohydrate microarrays. J. Fluor. Chem. 127, 571-579 (2006).
54. Dyukova VI, Dementieva EI, Zubtsov DA, Galanina OE, Bovin NV, Rubina AY. Hydrogel glycan microarrays. Anal. Biochem. 347(1), 94-105 (2005).
55. Blixt O, Head S, Mondala T et al. Printed covalent glycan array for ligand profiling of diverse glycan binding proteins. Proc. Natl Acad. Sci. USA 101(49), 17033-17038 (2004). •• Describes the analysis of an assortment of glycan-binding proteins on a carbohydrate array consisting of approximately 200 glycans.
56. Bochner BS, Alvarez RA, Mehta P et al. Glycan array screening reveals a candidate ligand for Siglec-8. J. Biol. Chem. 280(6), 4307-4312 (2005).
57. Guo Y, Feinberg H, Conroy E et al. Structural basis for distinct ligand-binding and targeting properties of the receptors DC-SIGN and DC-SIGNR. Nat. Struct. Mol. Biol. 11(7), 591-598 (2004).
58. Galanina OE, Mecklenburg M, Nifantiev NE, Pazynina GV, Bovin NV. GlycoChip: multiarray for the study of carbohydrate-binding proteins. Lab Chip 3(4), 260-265 (2003).
59. de Paz JL, Noti C, Seeberger PH. Microarrays of synthetic heparin oligosaccharides. J. Am. Chem. Soc. 128(9), 2766-2767 (2006).
60. Tully SE, Rawat M, Hsieh-Wilson LC. Discovery of a TNF-α antagonist using chondroitin sulfate microarrays. J. Am. Chem. Soc. 128(24), 7740-7741 (2006).
61. Biskup MB, Muller JU, Weingart R, Schmidt RR. New methods for the generation of carbohydrate arrays on glass slides and their evaluation. Chembiochem 6(6), 1007-1015 (2005).
62. Lee MR, Shin I. Fabrication of chemical microarrays by efficient immobilization of hydrazide-linked substances on epoxide-coated glass surfaces. Angew. Chem. Int. Ed. Engl. 44(19), 2881-2884 (2005).
63. Manimala JC, Li Z, Jain A, VedBrat S, Gildersleeve JC. Carbohydrate array analysis of anti-Tn antibodies and lectins reveals unexpected specificities: implications for diagnostic and vaccine development. Chembiochem 6(12), 2229-2241 (2005). Revealed substantial crossreactivity of three commonly used anti-Tn receptors.
64. Manimala JC, Roach TA, Li Z, Gildersleeve JC. High-throughput carbohydrate microarray analysis of 24 lectins. Angew. Chem. Int. Ed. Engl. 45(22), 3607-3610 (2006).
65. Manimala JC, Roach TA, Li Z, Gildersleeve JC. High-throughput carbohydrate microarray profiling of 27 antibodies demonstrates widespread specificity problems. Glycobiology 17(8), 17C-23C (2007).
66. Ratner DM, Adams EW, Su J, O'Keefe BR, Mrksich M, Seeberger PH. Probing protein-carbohydrate interactions with microarrays of synthetic oligosaccharides. Chembiochem 5(3), 379-382 (2004).
67. Brun MA, Disney MD, Seeberger PH. Miniaturization of microwave-assisted carbohydrate functionalization to create oligosaccharide microarrays. Chembiochem 7(3), 421-424 (2006).
68. Houseman BT, Mrksich M. Carbohydrate arrays for the evaluation of protein binding and enzymatic modification. Chem. Biol. 9(4), 443-454 (2002).
69. Xia B, Kawar ZS, Ju T, Alvarez RA, Sachdev GP, Cummings RD. Versatile fluorescent derivatization of glycans for glycomic analysis. Nat. Methods 2(11), 845-850 (2005).
70. Park S, Lee MR, Pyo SJ, Shin I. Carbohydrate chips for studying highthroughput carbohydrate-protein interactions. J. Am. Chem. Soc. 126(15), 4812-4819 (2004).
71. Park S, Shin I. Fabrication of carbohydrate chips for studying protein-carbohydrate interactions. Angew. Chem. Int. Ed. Engl. 41(17), 3180-3182 (2002).
72. Yamamoto K, Ito S, Yasukawa F, Konami Y, Matsumoto N. Measurement of the carbohydrate-binding specificity of lectins by a multiplexed bead-based flow cytometric assay. Anal. Biochem. 336(1), 28-38 (2005).
73. Satoh A, Kojima K, Koyama T, Ogawa H, Matsumoto I. Immobilization of saccharides and peptides on 96-well microtiter plates coated with methyl vinyl ether-maleic anhydride copolymer. Anal. Biochem. 260(1), 96-102 (1998).
74. Lee MR, Shin I. Facile preparation of carbohydrate microarrays by site-specific, covalent immobilization of unmodified carbohydrates on hydrazide-coated glass slides. Org. Lett. 7(19), 4269-4272 (2005).
75. Zhi ZL, Powell AK, Turnbull JE. Fabrication of carbohydrate microarrays on gold surfaces: direct attachment of nonderivatized oligosaccharides to hydrazide-modified self-assembled monolayers. Anal. Chem. 78(14), 4786-4793 (2006).
76. Zhou X, Zhou J. Oligosaccharide microarrays fabricated on aminooxyacetyl functionalized glass surface for characterization of carbohydrate-protein interaction. Biosens. Bioelectron. 21(8), 1451-1458 (2006).
77. Angeloni S, Ridet JL, Kusy N et al. Glycoprofiling with micro-arrays of glycoconjugates and lectins. Glycobiology 15(1), 31-41 (2005).
78. Boyd MR, Gustafson KR, McMahon JB et al. Discovery of cyanovirin-N, a novel human immunodeficiency virusinactivating protein that binds viral surface envelope glycoprotein gp120: potential applications to microbicide development. Antimicrob. Agents Chemother. 41(7), 1521-1530 (1997).
79. Bokesch HR, O'Keefe BR, McKee TC et al. A potent novel anti-HIV protein from the cultured cyanobacterium Scytonema varium. Biochemistry 42(9), 2578-2584 (2003).
80. Kehr JC, Zilliges Y, Springer A et al. A mannan binding lectin is involved in cell-cell attachment in a toxic strain of Microcystis aeruginosa. Mol. Microbiol. 59(3), 893-906 (2006).
81. Mori T, O'Keefe BR, Sowder RC 2nd et al. Isolation and characterization of griffithsin, a novel HIV-inactivating protein, from the red alga Griffithsia sp. J. Biol. Chem. 280(10), 9345-9353 (2005).
82. Burton DR, Pyati J, Koduri R et al. Efficient neutralization of primary isolates of HIV-1 by a recombinant human monoclonal antibody. Science 266(5187), 1024-1027 (1994).
83. Trkola A, Purtscher M, Muster T et al. Human monoclonal antibody 2G12 defines a distinctive neutralization epitope on the gp120 glycoprotein of human immunodeficiency virus type 1. J. Virol. 70(2), 1100-1108 (1996).
84. Buchacher A, Predl R, Strutzenberger K et al. Generation of human monoclonal antibodies against HIV-1 proteins; electrofusion and Epstein-Barr virus transformation for peripheral blood lymphocyte immortalization. AIDS Res. Hum. Retroviruses 10(4), 359-369 (1994).
85. Mascola JR, Stiegler G, VanCott TC et al. Protection of macaques against vaginal transmission of a pathogenic HIV-1/SIV chimeric virus by passive infusion of neutralizing antibodies. Nat. Med. 6(2), 207-210 (2000).
86. Scanlan CN, Pantophlet R, Wormald MR et al. The broadly neutralizing anti-human immunodeficiency virus type 1 antibody 2G12 recognizes a cluster of α1 - >2 mannose residues on the outer face of gp120. J. Virol. 76(14), 7306-7321 (2002).
87. Adams EW, Ratner DM, Bokesch HR, McMahon JB, O'Keefe BR, Seeberger PH. Oligosaccharide and glycoprotein microarrays as tools in HIV glycobiology; glycan-dependent gp120/protein interactions. Chem. Biol. 11(6), 875-881 (2004). •• One of the original studies that shows the utility of carbohydrate arrays for studying glycan-protein interactions, including four gp120-binding proteins.
88. Calarese DA, Lee HK, Huang CY et al. Dissection of the carbohydrate specificity of the broadly neutralizing anti-HIV-1 antibody 2G12. Proc. Natl Acad. Sci. USA 102(38), 13372-13377 (2005). •• Presents a study on the use of a carbohydrate arrays to further probe 2G12-oligomannose structural requirements and determine binding affinities.
89. Daubenspeck JM, Zeng H, Chen P et al. Novel oligosaccharide side chains of the collagen-like region of BclA, the major glycoprotein of the Bacillus anthracis exosporium. J. Biol. Chem. 279(30), 30945-30953 (2004).
90. Wang D, Carroll GT, Turro NJ et al. Photogenerated glycan arrays identify immunogenic sugar moieties of Bacillus anthracis exosporium. Proteomics 7(2), 180-184 (2007). • Describes the use of a glycan array to identify carbohydrate antigen on bacteria.
91. Dinglasan RR, Fields I, Shahabuddin M, Azad AF, Sacci JB Jr. Monoclonal antibody MG96 completely blocks Plasmodium yoelii development in Anopheles stephensi. Infect. Immun. 71(12), 6995-7001 (2003).
92. Dinglasan RR, Valenzuela JG, Azad AF. Sugar epitopes as potential universal disease transmission blocking targets. Insect Biochem. Mol. Biol. 35(1), 1-10 (2005).
93. Kudryashov V, Ragupathi G, Kim IJ et al. Characterization of a mouse monoclonal IgG3 antibody to the tumor-associated Globo H structure produced by immunization with a synthetic glycoconjugate. Glycoconj. J. 15(3), 243-249 (1998).
94. Huang CY, Thayer DA, Chang AY et al. Carbohydrate microarray for profiling the antibodies interacting with Globo H tumor antigen. Proc. Natl Acad. Sci. USA 103(1), 15-20 (2006).
95. Lawrie CH, Marafioti T, Hatton CS et al. Cancer-associated carbohydrate identification in Hodgkin's lymphoma by carbohydrate array profiling. Int. J. Cancer 118(12), 3161-3166 (2006). • Reports identification of disease-associated carbohydrate antigens by profiling human sera.
96. He Y, Jiang S. Vaccine design for severe acute respiratory syndrome coronavirus. Viral Immunol. 18(2), 327-332 (2005).
97. Zhang JS, Chen JT, Liu YX et al. A serological survey on neutralizing antibody titer of SARS convalescent sera. J. Med. Virol. 77(2), 147-150 (2005).
98. Wang D, Lu J. Glycan arrays lead to the discovery of autoimmunogenic activity of SARS-CoV. Physiol. Genomics 18(2), 245-248 (2004). • Describes application of carbohydrate arrays to evaluating immune response to a vaccine.
99. Wall DA, Wilson G, Hubbard AL. The galactose-specific recognition system of mammalian liver: the route of ligand internalization in rat hepatocytes. Cell 21(1), 79-93 (1980).
100. Schwartz AL, Fridovich SE, Knowles BB, Lodish HF. Characterization of the asialoglycoprotein receptor in a continuous hepatoma line. J. Biol. Chem. 256(17), 8878-8881 (1981).
101. Sanchez JF, Lescar J, Chazalet V et al. Biochemical and structural analysis of Helix pomatia agglutinin. A hexameric lectin with a novel fold. J. Biol. Chem. 281(29), 20171-20180 (2006).
102. Singh T, Wu JH, Peumans WJ et al. Carbohydrate specificity of an insecticidal lectin isolated from the leaves of Glechoma hederacea (ground ivy) towards mammalian glycoconjugates. Biochem. J. 393(Pt 1), 331-341 (2006).
103. Ito Y, Hikino M, Yajima Y et al. Structural characterization of the epitopes of the monoclonal antibodies 473HD, CS-56, and MO-225 specific for chondroitin sulfate D-type using the oligosaccharide library. Glycobiology 15(6), 593-603 (2005).
104. Consortium for Functional Glycomics www.functionalglycomics.org