Chemoenzymatic Synthesis and Antibody Detection of DNA Glycoconjugates

Bioconjugate Chemistry

Volumn 14, Issue 6, 2003, Pages 1314-1322

  Wang, Yingli ^a   Sheppard, Terry L ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBODIES; CARBOHYDRATES; CHEMICAL DETECTION; ELECTROPHORESIS; MASS SPECTROMETRY; OLIGONUCLEOTIDES; SYNTHESIS (CHEMICAL);

ANTIBODY DETECTION; CHEMO-ENZYMATIC SYNTHESIS; CHEMOENZYMATIC APPROACHES; DETECTION PROTOCOLS; EFFICIENT SYNTHESIS; GLYCOCONJUGATES; LEWIS X; N-ACETYLGLUCOSAMINE; PHOSPHORAMIDITES; SYNTHESISED;

DNA;

ANTIBODY DETECTION; ARTICLE; CHEMICAL ANALYSIS; CHEMOLUMINESCENCE; CONJUGATION; DNA SYNTHESIS; ENZYME SYNTHESIS; GEL ELECTROPHORESIS; GENE TARGETING; GLYCOSYLATION; HYBRIDIZATION; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; QUANTITATIVE ANALYSIS; SOLID; SOUTHWESTERN BLOTTING; THERMAL ANALYSIS; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 0344925620     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc034144p     Document Type: Article

References (57)

1. Dwek, R. A. (1996) Glycobiology: Toward understanding the function of sugars. Chem. Rev. 96, 683-720.
2. Gorelik, E., Galili, U., and Raz, A. (2002) On the role of cell surface carbohydrates and their binding proteins (lectins) in tumor metastasis. Cancer Metastasis Rev. 20, 245-277.
3. Ritchie, G. E., Moffatt, B. E., Sim, R. B., Morgan, B. P., Dwek, R. A., and Rudd, P. M. (2002) Glycosylation and the complement system. Chem. Rev. 102, 305-319.
4. McEver, R. P. (1997) Selectin-carbohydrate interactions during inflammation and metastasis. Glycoconjugate J. 14, 585-591.
5. Feizi, T. (1997) Carbohydrate differentiation antigens Ii, SSEA-1 (Lex) and related structures. New Compr. Biochem. 29b, 571-586.
6. Cummings, R. D., and Nyame, A. K. (1996) Glycobiology of schistosomiasis. FASEB J. 10, 838-848.
7. Edwards, N. J., Monteiro, M. A., Faller, G., Walsh, E. J., Moran, A. P., Roberts, I. S., and High, N. J. (2000) Lewis X structures in the 0 antigen side-chain promote adhesion of Helicobacter pylori to the gastric epithelium. Mol. Microbiol. 35, 1530-1539.
8. Garratty, G. (1995) Blood group antigens as tumor markers, parasitic/bacterial/viral receptors, and their association with immunologically important proteins. Immunol. Invest. 24, 213-232.
9. Lis, H., and Sharon, N. (1998) Lectins: Carbohydratespecific proteins that mediate cellular recognition. Chem. Rev. 98, 637-674.
10. Singhal, A., and Hakomori, S. (1990) Molecular changes in carbohydrate antigens associated with cancer. BioEssays 12, 223-230.
11. Van Dam, G. J., Bergwerff, A. A., Thomas-Oates, J. E., Rotmans, J. P., Kamerling, J. P., Vliegenthart, J. F. G., and Deelder, A. M. (1994) The immunologically reactive 0-linked polysaccharide chains derived from circulating cathodic antigen isolated from the human blood fluke Schistosoma mansoni have Lewis x as repeating unit. Eur. J. Biochem. 225, 467-482.
12. Pan, J., Yeger, H., and Cutz, E. (2002) Neuronal developmental marker FORSE-1 identifies a putative progenitor of the pulmonary neuroendocrine cell lineage during lung development. J. Histochem. Cytochem. 50, 1567-1578.
13. Sears, P., and Wong, C.-H. (1999) Carbohydrate mimetics: a new strategy for tackling the problem of carbohydrate-mediated biological recognition. Angew. Chem., Int. Ed. 38, 2301-2324.
14. Sihorkar, V., and Vyas, S. P. (2001) Potential of polysaccharide anchored liposomes in drug delivery, targeting and immunization. J. Pharm. Pharmaceut. Sci. 4, 138-158.
15. Cloninger, M. J. (2002) Biological applications of dendrimers. Curr. Opin. Chem. Biol. 6, 742-748.
16. Stiriba, S.-E., Frey, H., and Haag, R. (2002) Dendritic polymers in biomedical applications: From potential to clinical use in diagnostics and therapy. Angew. Chem., Int. Ed. 41, 1329-1334.
17. Lichtenstein, J., and Cohen, S. S. (1960) Nucleotides derived from enzymatic digests of nucleic acids of T2, T4, and T6 bacteriophages. J. Biol. Chem. 235, 1134-1141.
18. Lehman, I. R., and Pratt, E. A. (1960) On the structure of the glucosylated hydroxymethylcytosine nucleotides of coliphages T2, T4, and T6. J. Biol. Chem. 235, 3254-3259.
19. Ehrlich, M., and Ehrlich, K. C. (1981) A novel, highly modified, bacteriophage DNA in which thymine is partly replaced by a phosphoglucuronate moiety covalently bound to 5-(4′, 5′-dihydroxypentyl)uracil. J. Biol. Chem. 256, 9966-9972.
20. Gommers-Ampt, J. H., Vanleeuwen, F., Debeer, A. L. J., Vliegenthart, J. F. G., Dizdaroglu, M., Kowalak, J. A., Crain, P. F., and Borst, P. (1993) β-D-Glucosyl-hydroxymethyluracil - a novel modified base present in the DNA of the parasitic protozoan trypanosoma-brucei. Cell 75, 1129-1136.
21. van Leeuwen, F., Taylor, M. C., Mondragon, A., Moreau, H., Gibson, W., Kieft, R., and Borst, P. (1998) β-D-glucosyl-hydroxymethyluracil is a conserved DNA modification in kinetoplastid protozoans and is abundant in their telomeres. Proc. Natl. Acad. Sci. U.S.A. 95, 2366-2371.
22. Borst, P., and van Leeuwen, F. (1997) β -D-Glucosyl-hydroxymethyluracil, a novel base in African trypanosomes and other Kinetoplastida. Mol. Biochem. Parasitol. 90, 1-8.
23. van Leeuwen, F., Kieft, R., Cross, M., and Borst, P. (2000) Tandemly repeated DNA is a target for the partial replacement of thymine by β-D-glucosyl-hydroxymethyluracil in Trypanosoma brucei. Mol. Biochem. Parasitol. 109,133-145.
24. Akhtar, S., Routledge, A., Patel, R., and Gardiner, J. M. (1995) Synthesis of monomannoside and dimannoside phosphoramidite derivatives for solid-phase conjugation to oligonucleotides. Tetrahedron Lett. 36, 7333-7336.
25. de Kort, M., Ebrahimi, E., Wijsman, E. R., van der Marel, G. A., and van Boom, J. H. (1999) Synthesis of oligodeoxy-nucleotides containing 5-(β-D-glycopyranosyloxymethyl)-2′-deoxyuridine, a modified nucleoside in the DNA of Trypanosoma brucei. Eur. J. Org. Chem., 2337-2344.
26. Sheppard, T. L., Wong, C. H., and Joyce, G. F. (2000) Nucleoglycoconjugates: Design and synthesis of a new class of DNA-carbohydrate conjugates. Angew. Chem., Int. Ed. 39, 3660-3663.
27. Matsuura, K., Hibino, M., Yamada, Y., and Kobayashi, K. (2001) Construction of glyco-clusters by self-organization of site-specifically glycosylated oligonucleotides and their cooperative amplification of lectin-recognition. J. Am. Chem. Soc. 123, 357-358.
28. Dubber, M., and Frechet, J. M. J. (2003) Solid-phase synthesis of multivalent glycoconjugates on a DNA synthesizer. Bioconjugate Chem. 14, 239-246.
29. Matsuura, K., Akasaka, T., Hibino, M., and Kobayashi, K. (2000) Facile synthesis of stable and lectin-recognizable DNA-carbohydrate conjugates via diazo coupling. Bioconjugate Chem. 11, 202-211.
30. Dey, S., and Sheppard, T. L. (2001) Ketone-DNA: A versatile postsynthetic DNA decoration platform. Org. Lett. 3, 3983-3986.
31. Charles, I., Xue, L. A., and Arya, D. P. (2002) Synthesis of aminoglycoside-DNA conjugates. Bioorg. Med. Chem. Lett. 12, 1259-1262.
32. Koeller, K. M., and Wong, C. H. (2000) Synthesis of complex carbohydrates and glycoconjugates: Enzyme-based and programmable one-pot strategies. Chem. Rev. 100, 4465-4493.
33. Davis, B. G. (2002) Synthesis of glycoproteins. Chem. Rev. 102, 579-601.
34. Flitsch, S. L. (2000) Chemical and enzymatic synthesis of glycopolymers. Curr. Opin. Chem. Biol. 4, 619-625.
35. Ichikawa, Y., Lin, Y. C., Dumas, D. P., Shen, G. J., Garciajunceda, E., Williams, M. A., Bayer, R., Ketcham, C., Walker, L. E., Paulson, J. C., and Wong, C. H. (1992) Chemical-enzymatic synthesis and conformational-analysis of sialyl lewis-X and derivatives. J. Am. Chem. Soc. 114, 9283-9298.
36. Seitz, 0., and Wong, C. H. (1997) Chemoenzymatic solution- and solid-phase synthesis of 0-glycopeptides of the mucin domain of MAdCAM-1. A general route to O-LacNAc, 0-sialyl-LacNAc, and 0-sialyl-Lewis-X peptides. J. Am. Chem. Soc. 119, 8766-8776.
37. Halcomb, R. L., Huang, H. M., and Wong, C. H. (1994) Solution-phase and solid-phase synthesis of inhibitors of Helicobacter-pylori attachment and E-selectin-mediated leukocyte adhesion. J. Am. Chem. Soc. 116, 11315-11322.
38. Matsuda, M. (2001) Heterobifunctional ligands: Practical chemoenzymatic synthesis of a cell adhesive glycopeptide that interacts with both selectins and integrins. J. Med. Chem. 44, 715-724.
39. Danishefsky, S. J., Koseki, K., Griffith, D. A., Gervay, J., Peterson, J. M., McDonald, F. E., and Oriyama, T. (1992) Azaglycosylation of complex stannyl alkoxides with glycal-derived iodo sulfonamides: a straightforward synthesis of sialyl-Lewis X antigen and other oligosaccharide domains. J. Am. Chem. Soc. 114, 8331-8333.
40. Danishefsky, S. J., Gervay, J., Peterson, J. M., McDonald, F. E., Koseki, K., Oriyama, T., Griffith, D. A., Wong, C. H., and Dumas, D. P. (1992) Remarkable regioselectivity in the chemical glycosylation of glycal acceptors: a concise solution to the synthesis of sialyl-Lewis X glycal. J. Am. Chem. Soc. 114, 8329-8331.
41. Corey, E. J., and Roberts, B. E. (1997) Total synthesis of dysidiolide. J. Am. Chem. Soc. 119, 12425-12431.
42. Pochet, S., Kansal, V., Destouesse, F., and Sarfati, S. R. (1990) Alkylglycoside carbonates of 3′-azido-3′-deoxythymidine. Tetrahedron Lett. 31, 6021-6024.
43. Horton, D. (1973) 2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-α -D-glucopyranosyl chloride. Organic Synthesis, pp 1-5, Wiley, New York.
44. Bouzide, A., and Sauve, G. (1997) Highly selective silver-(I) oxide mediated monoprotection of symmetrical diols. Tetrahedron Lett. 38, 5945-5948.
45. Zemlyakov, A. E., Kakayan, E. S., and Chirva, V. Y. (1989) Synthesis of β-(ω-aminoalkyl)glycosides of N-acetylmuramoyl-L-alanyl-D-isoglutamine. Bioorg. Khim. 15, 1527-1533.
46. Richards, E. G. (1975) Use of tables in calculation of absorption, optical rotatory dispersion, and circular dichroism of polyribonucleotides. Handbook of Biochemistry and Molecular Biology: Nucleic Acids, 3rd ed., pp 596-603, CRC Press, Cleveland.
47. Bhattacharyya, B. R., Ramaswamy, K., and Crane, R. K. (1976) Synthesis of some β-D-glucopyranosides having a hydrophobic aglycon group terminated with a hydrophilic group. Carbohydr. Res. 47, 167-171.
48. Charreyre, M. T., Boullanger, P., Pichot, C., Delair, T., Mandrand, B., and Llauro, M. F. (1993) Synthesis of a hexyl methacrylate-terminated disaccharide monomer and study of its radically initiated homo- and copolymerization with styrene. Makromol. Chem. 194, 117-135.
49. Ren, T., Zhang, G., and Liu, D. (2001) Synthesis of bifunctional cationic compounds for gene delivery. Tetrahedron Lett. 42, 1007-1010.
50. Heathcock, C. H., and Ratcliff, R. (1971) Stereoselective total synthesis of the guaiazulenic sesquiterpenoids α-bulnesene and bulnesol. J. Am. Chem. Soc. 93, 1746-1757.
51. Caruthers, M. H., Barone, A. D., Beaucage, S. L., Dodds, D. R., Fisher, E. F., Mcbride, L. J., Matteucci, M., Stabinsky, Z., and Tang, J. Y. (1987) Chemical synthesis of deoxyoligo-nucleotides by the phosphoramidite method. Methods Enzymol. 154, 287-313.
52. Weston, B. W., Smith, P. L., Kelly, R. J., and Lowe, J. B. (1992) Molecular cloning of a fourth member of a human α(l, 3)fucosyltransferase gene family. Multiple homologous sequences that determine expression of the Lewis x, sialyl Lewis x, and difucosyl sialyl Lewis x epitopes. J. Biol. Chem. 267, 24575-24584.
53. Geyer, H., Schmitt, S., Wuhrer, M., and Geyer, R. (1999) Structural analysis of glycoconjugates by on-target enzymatic digestion and MALDI-TOF-MS. Anal. Chem. 71, 476-482.
54. Southern, E. M. (1975) Detection of specific sequences among DNA fragments separated by gel electrophoresis. J. Mol. Biol. 98, 503-517.
55. Remoortere, A., Hokke, C. H., van Dam, G. J., van Die, I., Deelder, A. M., and van den Eijnden, D. H. (2000) Various stages of schistosoma express Lewis(x), LacdiNAc, GalNAcβ1-4 (Fucα1-3)GlcNAc and GalNAcβ1-4(Fucα1-2Fucα1-3)GlcNAc carbohydrate epitopes: detection with monoclonal antibodies that are characterized by enzymatically synthesized neoglycoproteins. Glycobiology 10, 601-609.
56. Allendoerfer, K. L., Durairaj, A., Matthews, G. A., and Patterson, P. H. (1999) Morphological domains of Lewis-X/FORSE-1 immunolabeling in the embryonic neural tube are due to developmental regulation of cell surface carbohydrate expression. Dev. Biol. 211, 208-219.
57. Akhtar, S., Hughes, M. D., Khan, A., Bibby, M., Hussain, M., Nawaz, Q., Double, J., and Sayyed, P. (2000) The delivery of antisense therapeutics. Adv. Drug Delivery Rev. 44, 3-21.