Chemical conjugation of biomacromolecules: A mini-review

Chemical Papers

Volumn 64, Issue 6, 2010, Pages 683-695

  Farkaš, Pavol ^a   Bystrický, Slavomír ^a  

^a INSTITUTE OF CHEMISTRY   (Slovakia)

Author keywords

bioconjugation; chemical ligation; coupling; glycoconjugate

Indexed keywords

EID: 77957017140     PISSN: 03666352     EISSN: 13369075     Source Type: Journal    
DOI: 10.2478/s11696-010-0057-z     Document Type: Review

References (68)

1. Albericio, F. (2004). Developments in peptide and amide synthesis. Current Opinion in Chemical Biology, 8, 211-221. DOI: 10. 1016/j. cbpa. 2004. 03. 002.
2. Amir-Kroll, H., Nussbaum, G., & Cohen, I. R. (2003). Proteins and their derived peptides as carriers in a conjugate vaccine for Streptococcus pneumoniae: Self-heat shock protein 60 and tetanus toxoid. The Journal of Immunology, 170, 6165-6171.
3. Anderson, P., Pichichero, M. E., & Insel, R. A. (1985). Immunogens consisting of oligosaccharides from the capsule of Haemophilus influenzae type b coupled to diphtheria toxoid or CRM197. The Journal of Clinical Investigation, 76, 52-59. DOI: 10. 1172/JCI111976.
4. Baskin, J. M., Prescher, J. A., Laughlin, S. T., Agard, N. J., Chang, P. V., Miller, I, A., Lo, A., Codelli, J. A., & Bertozzi, C. R. (2007). Copper-free click chemistry for dynamic in vivo imaging. Proceedings of the National Academy of Sciences, 104, 16793-16797. DOI: 10. 1073/pnas. 0707090104.
5. Bauminger, S., & Wilcheck, M. (1980). The use of carbodiimides in the preparation of immunizing conjugates. Methods in Enzymology, 70, 151-159.
6. Berkin, A., Coxon, B., & Pozsgay, V. (2002). Towards a synthetic glycoconjugate vaccine against Neisseria meningitidis A. Chemistry - A European Journal, 8, 4424-4433. DOI: 10.1002/1521-3765(20021004)8:19<4424::AID-CHEM4424>3.0.CO;2-1.
7. Bernstein, M. A., & Hall, L. D. (1980). A general synthesis of model glycoproteins: coupling of alkenyl glycosides to proteins, using reductive ozonolysis followed by reductive amination with sodium cyanoborohydride. Carbohydrate Research, 78, C1-C3. DOI: 10. 1016/S0008-6215(00)83676-9.
8. Bode, J. W., Fox, R. M., & Baucom, K. D. (2006). Chemoselective amide ligations by decarboxylative condensations of N-alkylhydroxylamines and α-ketoacids. Angewandte Chemie International Edition, 45, 1248-1252. DOI: 10. 1002/anie. 200503991.
9. Boratyńsky, J., & Roy, R. (1998). High temperature conjugation of proteins with carbohydrates. Glycoconjugate Journal, 15, 131-138. DOI: 10. 1023/A: 1007067513242.
10. Bulpitt, P., & Aeschlimann, D. (1999). New strategy for chemical modification of hyaluronic acid: Preparation of functionalized derivatives and their use in the formation of novel biocompatible hydrogels. Journal of Biomedical Materials Research Part A, 47, 152-169. DOI:10.1002/(SICI)1097-4636(199911)47:2<152::AID-JBM5>3.0.CO; 2-I.
11. Bystrický, S., Machová, E., Bartek, P., Kolarova, N., & Kogan, G. (2000). Conjugation of yeast mannans with protein employing cyanopyridinium agent (CDAP). an effective route of antifungal vaccine preparation. Glycoconjugate Journal, 17, 677-680. DOI: 10. 1023/A: 1011002118819.
12. Canalle, L. A., Löwik, D. W. P. M., & Hest, J. C. M. (2010). Polypeptide-polymer bioconjugates. Chemical Society Reviews, 39, 329-353, DOI: 10. 1039/b807871h.
13. Chan, T. R., Hilgraf, R., Sharpless, K. B., & Fokin, V. V. (2004). Polytriazoles as copper(I)-stabilizing ligands in catalysis. Organic Letters, 6, 2853-2855. DOI: 10. 1021/ol0493094.
14. 3. Analytical and Bioanalytical Chemistry, 381, 1130-1137. DOI: 10. 1007/s00216-004-3028-9.
15. Dawson, P. E., Muir, T. W., Clark-Lewis, I., & Kent, S. B. (1994). Synthesis of proteins by native chemical ligation. Science, 266, 776-779. DOI: 10. 1126/science. 7973629.
16. Ďurana, R., Lacík, I., Paulovičová, E., & Bystický, S. (2006). Functionalization of mannans from pathogenic yeasts by different means of oxidations-preparation of precursors for conjugation reactions with respect to preservation of immunological properties. Carbohydrate Polymers, 63, 72-81. DOI: 10. 1016/j. carbpol. 2005. 08. 003.
17. Dziadek, S., Jacques, S., & Bundle, D. R. (2008). A novel linker methodology for the synthesis of tailored conjugate vaccines composed of complex carbohydrate antigens and specific THcell peptide epitopes. Chemistry - A European Journal, 14, 5908-5917. DOI: 10. 1002/chem. 200800065.
18. Farkaš, P., & Bystrický, S. (2008). Hydrolysis of the terminal dimethylacetal moiety on the spacers bound to carboxy groups containing glucans. Carbohydrate Polymers, 74, 133-136. DOI: 10. 1016/j. carbpol. 2008. 01. 005.
19. Farkaš, P., & Bystický, S. (2007). Efficient activation of carboxyl polysaccharides for the preparation of conjugates. Carbohydrate Polymers, 68, 187-190. DOI: 10. 1016/j. carbpol. 2006. 07. 013.
20. García, A., Hernández, K., Chico, B., García, D., Villalonga, M. L., & Villalonga, R. (2009). Preparation of thermostable trypsin. polysaccharide neoglycoenzymes through Ugi multicomponent reaction. Journal of Molecular Catalysis B: Enzymatic, 59, 126-130. DOI: 10. 1016/j. molcatb. 2009. 02. 001.
21. Grabarek, Z., & Gergely, J. (1990). Zero-length crosslinking procedure with the use of active esters. Analytical Biochemistry, 185, 131-135. DOI: 10. 1016/0003-2697(90)90267-D.
22. Grandjean, C., Boutonnier, A., Dassy, B., Fournier, J.-M., & Mulard, L. A. (2009). Investigation towards bivalent chemically defined glycoconjugate immunogens prepared from acid-detoxified lipopolysaccharide of Vibrio cholerae O1, serotype Inaba. Glycoconjugate Journal, 26, 41-55. DOI: 10. 1007/s10719-008-9160-6.
23. Grandjean, C., Boutonnier, A., Guerreiro, C., Fournier, J.-M., & Mulard, L. A. (2005). On the preparation of carbohydrate-protein conjugates using the traceless Staudinger ligation. Journal of the Organic Chemistry, 70, 7123-7132. DOI: 10. 1021/jo0505472.
24. Griesbaum, K. (1970). Problems and possibilities of the free-radical addition of thiols to unsaturated compounds. Angewandte Chemie International Edition, 9, 273-287. DOI: 10. 1002/anie. 197002731.
25. Gurd, F. R. N. (1967). Carboxymethylation. Methods in Enzymology, 11, 532-541. DOI: 10. 1016/S0076-6879(67)11064-1.
26. Hermanson, G. T. (1996). Bioconjugate techniques. San Diego, CA, USA: Academic Press, Inc.
27. Hou, S.-J., Saksena, R., & Kova., P. (2008). Preparation of glycoconjugates by dialkyl squarate chemistry revisited. Carbohydrate Research, 343, 196-210. DOI: 10. 1016/j. carres. 2007. 10. 015.
28. Hoyle, C. E., & Bowman, C. N. (2010). Thiol-ene click chemistry. Angewandte Chemie International Edition, 49, 1540-1573. DOI: 10. 1002/anie. 200903924.
29. Izumi, M., Okumura, S., Yuasa, H., & Hashimoto, H. (2003). Mannose-BSA conjugates: Comparison between commercially available linkers in reactivity and bioactivity. Journal of Carbohydrate Chemistry, 22, 317-329. DOI: 10. 1081/CAR-120023475.
30. Johnson, E. C. B., & Kent, S. B. H. (2006). Insights into the mechanism and catalysis of the native chemical ligation reaction. Journal of the American Chemical Society, 128, 6640-6646. DOI: 10. 1021/ja058344i.
31. Jonkheijm, P., Weinrich, D., Köhn, M., Engelkamp, H., Christianen, P. C. M., Kuhlmann, J., Maan, J. C., Nüsse, D., Schroeder, H., Wacker, R., Breinbauer, R., Niemeyer, C. M., & Waldmann, H. (2008). Photochemical surface patterning by the thiol-ene reaction. Angewandte Chemie International Edition, 47, 4421-4424. DOI: 10. 1002/anie. 200800101.
32. Kiick, K. L., Saxon, E., Tirrell, D. A., & Bertozzi, C. R. (2002). Incorporation of azides into recombinant proteins for chemoselective modification by the Staudinger ligation. Proceedings of the National Academy of Sciences, 99, 19-24. DOI: 10. 1073/pnas. 012583299.
33. Kohn, J., & Wilchek, M. (1983). 1-Cyano-4-dimethylamino pyridinium tetrafluoroborate as a cyanylating agent for the covalent attachment of ligand to polysaccharide resins. FEBS Letters, 154, 209-210. DOI: 10. 1016/0014-5793(83)80905-3.
34. Köhn, M., & Breinbauer, R. (2004). The Staudinger ligation - a gift to chemical biology. Angewandte Chemie International Edition, 43, 3106-3116. DOI: 10. 1002/anie. 200401744.
35. Kubler-Kielb, J., Liu, T.-Y., Mocca, C., Majadly, F., Robbins, J. B., & Schneerson, R. (2006). Additional conjugation methods and immunogenicity of Bacillus anthracis poly-γ-D-glutamic acid-protein conjugates. Infection and Immunity, 74, 4744-4749. DOI: 10. 1128/IAI. 00315-06.
36. Kubler-Kielb, J., & Pozsgay, V. (2005). A new method for conjugation of carbohydrates to proteins using an aminooxy-thiol heterobifunctional linker. Journal of the Organic Chemistry, 70, 6987-6990. DOI: 10. 1021/jo050934b.
37. Lees, A., Sen, G., & Acosta, A. L. (2006). Versatile and efficient synthesis of protein. polysaccharide conjugate vaccines using aminooxy reagents and oxime chemistry. Vaccine, 24, 716-729. DOI: 10. 1016/j. vaccine. 2005. 08. 096.
38. Leung, C., Chibba, A., Gómez-Biagi, R. F., & Nitz, M. (2009). Efficient synthesis and protein conjugation of β-(1→6)-D-N-acetylglucosamine oligosaccharides from the polysaccharide intercellular adhesin. Carbohydrate Research, 344, 570-575. DOI: 10. 1016/j. carres. 2008. 12. 021.
39. Li, C.-J. (2005). Organic reactions in aqueous media with a focus on carbon. carbon bond formations: A decade update. Chemical Reviews, 105, 3095-3165. DOI: 10. 1021/cr030009u.
40. Lin, F. L., Hoyt, H. M., van Halbeek, H., Bergman, R. G., & Bertozzi, C. R. (2005). Mechanistic investigation of the Staudinger ligation. Journal of the American Chemical Society, 127, 2686-2695. DOI: 10. 1021/ja044461m.
41. Lutz, J.-F., & Börner, H. G. (2008). Modern trends in polymer bioconjugates design. Progress in Polymer Science, 33, 1-39. DOI: 10. 1016/j. progpolymsci. 2007. 07. 005.
42. Lutz, J.-F., & Zarafshani, Z. (2008). Efficient construction of therapeutics, bioconjugates, biomaterials and bioactive surfaces using azide. alkyne "click" chemistry. Advanced Drug Delivery Reviews, 60, 958-970. DOI: 10. 1016/j. addr. 2008. 02. 004.
43. Mieszala, M., Kogan, G., & Jennings, H. J. (2003). Conjugation of meningococcal lipooligosaccharides through their lipid A terminus conserves their inner epitopes and results in conjugate vaccines having improved immunological properties. Carbohydrate Research, 338, 167-175. DOI: 10. 1016/S0008-6215(02)00395-6.
44. Montalbetti, C. A. G. N., & Falque, V. (2005). Amide bond formation and peptide coupling. Tetrahedron, 61, 10827-10852. DOI: 10. 1016/j. tet. 2005. 08. 031.
45. Pavliakova, D., Chu, C., Bystrický, S., Tolson, N. W., Shiloach, J., Kaufman, J. B., Bryla, D. A., Robbins, J. B., & Schneerson, R. (1999). Treatment with succinic anhydride improves the immunogenicity of Shigella flexneri Type 2a O-specific polysaccharide-protein conjugates in mice. Infection and Immunity, 67, 5526-5529.
46. Pawlowski, A., Källenius, G., & Svenson, S. B. (2000). Preparation of pneumococcal capsular polysaccharide-protein conjugate vaccines utilizing new fragmentation and conjugation technologies. Vaccine, 18, 1873-1885. DOI: 10. 1016/S0264-410X(99)00336-9.
47. Pawlowski, A., Källenius, G., & Svenson, S. B. (1999). A new method of non-cross-linking conjugation of polysaccharides to proteins via thioether bonds for the preparation of saccharide. protein conjugate vaccines. Vaccine, 17, 1474-1483. DOI: 10. 1016/S0264-410X(98)00385-5.
48. Pozsgay, V., & Kubler-Kielb, J. (2008). Conjugation methods toward synthetic vaccines. In R. Roy (Ed.), Carbohydrate based vaccines (pp. 36-70). Washington, DC, USA: American Chemical Society.
49. Pozsgay, V., Vieira, N. E., & Yergey, A. (2002). A method for bioconjugation of carbohydrates using Diels-Alder cycloaddition. Organic Letters, 4, 3191-3194. DOI: 10. 1021/ol026179v.
50. Rideout, D. C., & Breslow, R. (1980). Hydrophobic acceleration of Diels-Alder reactions. Journal of the American Chemical Society, 102, 7816-7817. DOI: 10. 1021/ja00546a048.
51. Rodionov, V. O., Presolski, S. I., Gardinier, S., Lim, Y.-H., & Finn, M. G. (2007). Benzimidazole and related ligands for Cu-catalyzed azide-alkyne cycloaddition. Journal of the American Chemical Society, 129, 12696-12704. DOI: 10. 1021/ja072678l.
52. Rogers, L. K., Leinweber, B. L., & Smith, C. V. (2006). Detection of reversible protein thiol modifications in tissues. Analytical Biochemistry, 358, 171-184. DOI: 10. 1016/j. ab. 2006. 08. 020.
53. Rostovtsev, V. V., Green, L. G., Fokin, V. V., & Sharpless, K. B. (2002). A stepwise Huisgen cycloaddition process: Copper(I)-catalyzed regioselective ligation of azides and terminal alkynes. Angewandte Chemie International Edition, 41, 2596-2599. DOI: 10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4.
54. Sanki, A. K., Talan, R. S., & Sucheck, S. J. (2009). Synthesis of small glycopeptides by decarboxylative condensation and insight into the reaction mechanism. The Journal of Organic Chemisty, 74, 1886-1896. DOI: 10. 1021/jo802278w.
55. Saxon, E., & Bertozzi, C. R. (2000). Cell surface engineering by a modified Staudinger reaction. Science, 287, 2007-2010. DOI: 10. 1126/science. 287. 5460. 2007.
56. Schlottmann, S. A., Jain, N., Chirmule, N., & Esser, M. T. (2006). A novel chemistry for conjugating pneumococcal polysaccharides to Luminex microspheres. Journal of Immunological Methods, 309, 75-85. DOI: 10. 1016/j. jim. 2005. 11. 019.
57. Shafer, D. E., Toll, B., Schuman, R. F., Nelson, B. L., Mond, J. J., & Lees, A. (2000). Activation of soluble polysaccharides with 1-cyano-4-dimethylaminopyridinium tetrafluoroborate (CDAP) for use in protein-polysaccharide conjugate vaccines and immunological reagents. II. Selective crosslinking of proteins to CDAP-activated polysaccharides. Vaccine, 18, 1273-1281. DOI: 10. 1016/S0264-410X(99)00370-9.
58. Singh, R., & Whitesides, G. M. (1991). A reagent for reduction of disulfide bonds in proteins that reduces disulfide bonds faster than does dithiothreitol. Journal of Organic Chemistry, 56, 2332-2337. DOI: 10. 1021/jo00007a018.
59. Sletten, E. M., & Bertozzi, C. R. (2009). Bioorthogonal chemistry: Fishing for selectivity in a sea of functionality. Angewandte Chemie International Edition, 48, 6974-6998. DOI: 10. 1002/anie. 200900942.
60. Sletten, E. M., & Bertozzi, C. R. (2008). A hydrophilic azacyclooctyne for Cu-free click chemistry. Organic Letters, 10, 3097-3099. DOI: 10. 1021/ol801141k.
61. Soellner, M. B., Nilsson, B. L., & Raine, R. T. (2006). Reaction mechanism and kinetics of the traceless Staudinger ligation. Journal of the American Chemical Society, 128, 8820-8828. DOI: 10. 1021/ja060484k.
62. Staudinger, H., & Meyer, J. (1919). Über neue organische Phosphorverbindungen III. Phosphinmethylenderivate und phosphinimine. Helvetica Chimimica Acta, 2, 635-646. DOI: 10. 1002/hlca. 19190020164.
63. Tietze, L. F., Schröter, C., Gabius, S., Brinck, U., Goerlach-Graw, A., & Gabius, H.-J. (1991). Conjugation of paminophenyl glycosides with squaric acid diester to a carrier protein and the use of the neoglycoprotein in the histochemical detection of lectins. Bioconjugate Chemistry, 2, 148-153. DOI: 10. 1021/bc00009a003.
64. Wang, J. Y., Chang, A. H. C., Guttormsen, H.-K., Rosas, A. L., & Kaspe, D. L. (2002). Construction of designer glycoconjugate vaccines with size-specific oligosaccharide antigens and site-controlled coupling. Vaccine, 21, 1112-1117. DOI: 10. 1016/S0264-410X(02)00625-4.
65. Wang, Q., Chan, T. R., Hilgraf, R., Fokin, V. V., Sharpless, K. B., & Finn, M. G. (2003). Bioconjugation by copper(I)-catalyzed azide-alkine [3 + 2] cycloaddition. Journal of the American Chemical Society, 125, 3192-3193. DOI: 10. 1021/ja021381e.
66. Xin, H., Dziadek, S., Bundle, D. R., & Cutler, J. E. (2008). Synthetic glycopeptide vaccines combining β-mannan and peptide epitopes induce protection against candidiasis. Proceedings of the National Academy of Sciences, 105, 13526-13531. DOI: 10. 1073/pnas. 0803195105.
67. Xue, J., Pan, Y., & Guo, Z. (2002). Neoglycoprotein cancer vaccines: synthesis of an azido derivative of GM3 and its efficient coupling to proteins through a new linker. Tetrahedron Leters, 43, 1599-1602. DOI: 10. 1016/S0040-4039(02)00071-0.
68. Zhang, J., Yergey, A., Kowalak, J., & Kováč, P. (1998). Linking carbohydrates to proteins using N-(2, 2-dimethoxyethyl)-6-hydroxy hexanamide. Tetrahedron, 54, 11783-11792. DOI: 10. 1016/S0040-4020(98)83039-1.