Synthesis of multivalent neoglyconjugates of MUC1 by the conjugation of carbohydrate-centered, triazole-linked glycoclusters to MUC1 peptides using click chemistry

Journal of Organic Chemistry

Volumn 77, Issue 17, 2012, Pages 7564-7571

  Lee, Dong Jun ^a   Yang, Sung Hyun ^a   Williams, Geoffrey M ^a   Brimble, Margaret A ^a  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

1 ,3-DIPOLARCYCLOADDITION; CLICK CHEMISTRY; EFFICIENT SYNTHESIS; GLYCOPEPTIDES; NEOGLYCOCONJUGATES; PEPTIDE SEQUENCES; PROOF OF PRINCIPLES; PROPARGYL;

ACETYLENE; CARBOHYDRATES; CYCLOADDITION; GLUCOSE; NITROGEN COMPOUNDS; SYNTHESIS (CHEMICAL);

PEPTIDES;

ACETYLENE DERIVATIVE; AZIDE; CARBOHYDRATE DERIVATIVE; COPPER; GLYCOCONJUGATE; GLYCOPEPTIDE; MONOSACCHARIDE; MUCIN 1; MUCIN 1 NEOGLYCOCONJUGATE; PEPTIDE DERIVATIVE; PEPTIDOMIMETIC AGENT; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ARTICLE; BINDING AFFINITY; CATALYST; CHEMICAL PROCEDURES; CHEMICAL REACTION; CLICK CHEMISTRY; CYCLOADDITION; DRUG CONJUGATION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; REPRODUCIBILITY; STRUCTURE ANALYSIS;

ALKYNES; AZIDES; CARBOHYDRATES; CATALYSIS; CLICK CHEMISTRY; COPPER; CYCLIZATION; GLYCOCONJUGATES; MOLECULAR CONFORMATION; MUCIN-1; PEPTIDES; TRIAZOLES;

EID: 84866063594     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo3013435     Document Type: Article

References (69)

1. Chlubnova, I.; Sylla, B.; Nugier-Chauvin, C.; Daniellou, R.; Legentil, L.; Kralova, B.; Ferrieres, V. Nat. Prod. Rep. 2011, 28, 937-952
2. Mowery, P.; Yang, Z. Q.; Gordon, E. J.; Dwir, O.; Spencer, A. G.; Alon, R.; Kiessling, L. L. Chem. Biol. 2004, 11, 725-732
3. Bertozzi, C. R.; Kiessling, L. L. Science 2001, 291, 2357-2364
4. Dube, D. H.; Bertozzi, C. R. Nat. Rev. Drug Discovery 2005, 4, 477-488
5. Carbohydrates in Chemistry and Biology, Part II, Biology of Saccharides; Ernst, B.; Hart, G. W.; Sinay, P., Eds.; Wiley-VCH: Weinheim, 2000; Vol. 4, Lectins and Saccharide Biology.
6. Lee, Y. C.; Lee, R. T. Acc. Chem. Res. 1995, 28, 321-327
7. Mammen, M.; Choi, S. K.; Whitesides, G. M. Angew. Chem., Int. Ed. 1998, 37, 2754-2794
8. Lindquist, J. J.; Toone, E. J. Chem. Rev. 2002, 102, 555-578
9. Dam, T. K.; Brewer, C. F. Chem. Rev. 2002, 102, 387-429
10. Badjic, J. D.; Nelson, A.; Cantrill, S. J.; Turnbull, W. B.; Stoddart, J. F. Acc. Chem. Res. 2005, 38, 723-732
11. Choi, S. K. Synthetic Multivalent Molecules: Concept and Biomedical Application; John Wiley and Sons: Hoboken, NJ, 2005.
12. Grabosch, C.; Hartmann, M.; Schmidt-Lassen, J.; Lindhorst, T. K. ChemBioChem 2011, 12, 1066-1074
13. Schierholt, A.; Hartmann, Mirja; Lindhorst, T. K. Carbohydr. Res. 2011, 346, 1519-1526
14. Wehner, J. W.; Lindhorst, T. K. Synthesis 2010, 18, 3070-3082
15. Ladmiral, V.; Melia, E.; Haddleton, D. M. Eur. Polym. J. 2004, 40, 431-449
16. Voit, B.; Appelhaus, D. Macromol. Chem. Phys. 2010, 211, 727-735
17. Niederhafer, P.; Sebestik, J.; Jezek, J. J. Pept. Sci. 2008, 14, 2-43
18. Niederhafer, P.; Sebestik, J.; Jezek, J. J. Pept. Sci. 2008, 14, 44-65
19. Kolomiets, E.; Swiderska, M. A.; Kadam, R. U.; Johansson, E. M. V.; Jaeger, K.-E.; Darbre, T.; Reymond, J.-L. ChemMedChem 2009, 4, 562-569
20. Kadam, R. U.; Bergmann, M.; Hurley, M.; Garg, D.; Cacciarini, M.; Swiderska, M. A.; Nativi, C.; Sattler, M.; Smyth, A. R.; Williams, P.; Camara, M.; Stocker, A.; Darbre, T.; Reymond, J.-L. Angew. Chem., Int. Ed. 2011, 50, 10631-10635
21. Roy, R. Trends Glycosci. Glycotechnol. 2003, 15, 291-310
22. Cloniger, M. J. Curr. Opin. Chem. Biol. 2002, 6, 742-748
23. Renaudet, O. Mini Rev. Org. Chem. 2008, 5, 274-286
24. Bossu, I.; Sulc, M.; Krenek, K.; Dufour, E.; Garcia, J.; Berthet, N.; Dumy, P.; Kren, V.; Renaudet, O. Org. Biomol. Chem. 2011, 9, 1948-1959
25. Gorska, K.; Huang, K.-T.; Chaloin, O.; Winssinger, N. Angew. Chem., Int. Ed. 2009, 48, 7695-7700
26. Fulton, D. A.; Stoddart, F. J. Bioconjugate Chem. 2001, 12, 655-672
27. Baldini, L.; Casnati, A.; Sansone, F.; Ungaro, R. Chem. Soc. Rev. 2007, 36, 254-266
28. Dondoni, A.; Marra, A. Chem. Rev. 2010, 110, 4949-4977
29. Gao, Y.; Eguchi, A.; Kakehi, K.; Lee, Y. C. Org. Lett. 2004, 6, 3457-3460
30. Nierengarten, J.-F.; Iehl, J.; Oerthel, V.; Holler, M.; Illescas, B. M.; Munoz, A.; Martin, N.; Rojo, J.; Sanchez-Navarro, M.; Cecioni, S.; Vidal, S.; Buffet, K.; Durka, M.; Vincent, S. P. Chem. Commun. 2010, 46, 3860-3862
31. de la Fuente, J. M.; Penades, S. Biochim. Biophys. Acta, Gen. Subj. 2006, 1760, 636-651
32. Marradi, M.; Matin-Lomas; Penades, S. Adv. Carbohydr. Chem. Biochem. 2010, 64, 211-290
33. Simanek, E. E.; McGarvey, G. J.; Jablonski, J. A.; Wong, C.-H. Chem. Rev. 1998, 98, 833-862
34. Autar, R.; Khan, A. S.; Schad, M.; Hacker, J.; Liskamp, R. M. J.; Pieters, R. J. ChemBioChem 2003, 4, 1317-1325
35. Sharon, N. Biochim. Biophys. Acta, Gen. Subj. 2006, 1760, 527-537
36. Pieters, R. J. Med. Res. Rev. 2007, 27, 796-816
37. Kitov, P. I.; Sadowska, J. M.; Mulvey, G.; Armstrong, G. D.; Ling, H.; Pannu, N. S.; Read, R. J.; Bundle, D. R. Nature 2000, 403, 669-672
38. Shaunak, S.; Thomas, S.; Gianasi, E.; Godwin, A.; Jones, E.; Teo, I.; Mireskandari, K.; Luthert, P.; Duncan, R.; Patterson, S.; Khaw, P.; Brocchini, S. Nat. Biotechnol. 2004, 22, 977-984
39. Roy, R.; Baek, M. G. Rev. Mol. Biotechnol. 2002, 90, 291-309
40. Brimble, M. A.; Miller, N.; Williams, G. M. Recent Developments in Neoglycopeptide Synthesis. In Amino Acids, Peptides and Proteins in Organic Chemistry; Hughes, A. B., Ed.; Wiley-VCH: Weinheim, 2011; Vol. 4, Protection Reactions, Medicinal Chemistry, Combinatorial Synthesis, pp 359-392
41. Brimble, M. A.; Miller, N.; Williams, G. M. Int. J. Pept. Res. Ther. 2010, 16, 125-132
42. Lee, D. J.; Harris, P. W. R.; Brimble, M. A. Org. Biomol. Chem. 2011, 9, 1621-1626
43. Lee, D. J.; Mandal, K.; Harris, P. W. R.; Brimble, M. A.; Kent, S. B. H. Org. Lett. 2009, 11, 5270-5273
44. Miller, N.; Williams, G. M.; Brimble, M. A. Org. Lett. 2009, 11, 2409-2412
45. Tornoe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057-3064
46. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596-2599
47. Hanisch, F.-G.; Muller, S. Glycobiology 2000, 10, 439-449
48. Baldus, S. E.; Engelmann, K.; Hanisch, F.-G. Crit. Rev. Clin. Lab. Sci. 2004, 41, 189-231
49. Hilkens, J.; Ligtenberg, M. J. L.; Vos, H. L.; Litvinov, S. V. Trends Biochem. Sci. 1992, 17, 359-363
50. Sherblom, A. P.; Moody, C. E. Cancer Res. 1986, 46, 4543-4546
51. Keil, S.; Claus, C.; Dippold, W.; Kunz, H. Angew. Chem., Int. Ed. 2001, 40, 366-369
52. Dziadek, S.; Hobel, A.; Schmitt, E.; Kunz, H. Angew. Chem., Int. Ed. 2005, 44, 7630-7635
53. Dziadek, S.; Kowalczyk, D.; Kunz, H. Angew. Chem., Int. Ed. 2005, 44, 7624-7630
54. Westerlind, U.; Hobel, A.; Gaidzik, N.; Schmitt, E.; Kunz, H. Angew. Chem., Int. Ed. 2008, 47, 7551-7556
55. Kaiser, A.; Gaidzik, N.; Westerlind, U.; Kowalczyk, D.; Hobel, A.; Schmitt, E.; Kunz, H. Angew. Chem., Int. Ed. 2009, 48, 7551-7555
56. Kaiser, A.; Gaidzik, N.; Becker, T.; Menge, C.; Groh, K.; Cai, H.; Li, Y.-M.; Gerlitzki, B.; Schmitt, E.; Kunz, H. Angew. Chem., Int. Ed. 2010, 49, 3688-3692
57. Hoffmann-Röder, A.; Kaiser, A.; Wagner, S.; Gaidzik, N.; Kowalczyk, D.; Westerlind, U.; Gerlitzki, B.; Schmitt, E.; Kunz, H. Angew. Chem., Int. Ed. 2010, 49, 8498-8503
58. Chun, C. K. Y.; Payne, R. J. Aust. J. Chem. 2009, 62, 1339-1343
59. Wilkinson, B. L.; Malins, L. R.; Chun, C. K. Y.; Payne, R. J. Chem. Commun. 2010, 46, 6249-6251
60. Wilkinson, B. L.; Day, S; Malins, L. R; Apostolopoulos, V.; Payne, R. J. Angew. Chem., Int. Ed. 2011, 50, 1635-1639
61. Wilkinson, B. L.; Chun, C. K. Y.; Payne, R. J. Pept. Sci. 2011, 96, 137-146
62. Gao, Y.; Eguchi, A.; Kakehi, K.; Lee, Y. C. Bioorg. Med. Chem. 2005, 13, 6151-6157
63. Ortega-Munoz, M.; Morales-Sanfrutos, J.; Perez-Balderas, F.; Hernandew-Mateo, F.; Giron-Gonzalez, M. D.; Sevillano-Tripero, N.; Salto-Gonzalez, R.; Santoyo-Gonzalez, F. Org. Biomol. Chem. 2007, 5, 2291-2301
64. Perez-Balderas, F.; Morales-Sanfrutos, J.; Hernandez-Mateo, F.; Isac-Garcí?a, J.; Santoyo-Gonzalez, F. Eur. J. Org. Chem. 2009, 2441-2453
65. Bera, S.; Lindhardt, R. J. J. Org. Chem. 2011, 76, 3181-3193
66. Hong, S. Y.; Tobias, G.; Ballesteros, B.; El Oualid, F.; Errey, J. C.; Doores, K. J.; Kirkland, A. I.; Nellist, P. D.; Green, M. L. H.; Davis, B. G. J. Am. Chem. Soc. 2007, 129, 10966-10967
67. Gyorgydeak, Z.; Szilagyi, L. Carbohydr. Res. 1985, 143, 21-41
68. Soli, E. D.; Manoso, A. S.; Patterson, M. C.; DeShong, P.; Favor, D. A.; Hirschmann, R.; Smith, A. B. J. Org. Chem. 1999, 64, 3171-3177
69. Harris, P. W. R.; Yang, S. H.; Brimble, M. A. Tetrahedron Lett. 2011, 52, 6024-6026