Biologically Active Heteroglycoclusters Constructed on a Pillar[5]arene-Containing [2]Rotaxane Scaffold

Chemistry - A European Journal

Volumn 22, Issue 1, 2016, Pages 88-92

  Vincent, Stéphane P ^a   Buffet, Kevin ^a   Nierengarten, Iwona ^b   Imberty, Anne ^c   Nierengarten, Jean François ^b  

^a UNIVERSITY OF NAMUR   (Belgium)

^b UNIVERSITÉ DE STRASBOURG   (France)

^c UNIV GRENOBLE ALPES   (France)

Author keywords

click chemistry; glycoclusters; lectin; pillar 5 arenes; rotaxane

Indexed keywords

PROTEINS; SCAFFOLDS; SELF ASSEMBLY; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS (CHEMICAL);

CLICK CHEMISTRY; GLYCOCLUSTERS; LECTIN; PILLAR[5]ARENES; ROTAXANES;

MOLECULAR ELECTRONICS;

GALACTOSE; LECTIN; ROTAXANE;

CELLULAR, SUBCELLULAR AND MOLECULAR BIOLOGICAL PHENOMENA AND FUNCTIONS; CHEMICAL STRUCTURE; CHEMISTRY; CLICK CHEMISTRY; PSEUDOMONAS AERUGINOSA;

BIOLOGICAL PHENOMENA; CLICK CHEMISTRY; GALACTOSE; LECTINS; MOLECULAR STRUCTURE; PSEUDOMONAS AERUGINOSA; ROTAXANES;

EID: 84954399860     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201504110     Document Type: Article

References (67)

1. I. Nierengarten, J.-F. Nierengarten, Chem. Rec. 2015, 15, 31-51.
2. S. Guerra, J. Iehl, M. Holler, M. Peterca, D. A. Wilson, B. E. Partridge, S. Zhang, R. Deschenaux, J.-F. Nierengarten, V. Percec, Chem. Sci. 2015, 6, 3393-3401;
3. I. Nierengarten, S. Guerra, M. Holler, J.-F. Nierengarten, R. Deschenaux, Chem. Commun. 2012, 48, 8072-8074;
4. S. Pan, M. Ni, B. Mu, Q. Li, X.-Y. Hu, C. Lin, D. Chen, L. Wang, Adv. Funct. Mater. 2015, 25, 3571-3580.
5. K. Yoosaf, J. Iehl, I. Nierengarten, M. Hmadeh, A.-M. Albrecht-Gary, J.-F. Nierengarten, N. Armaroli, Chem. Eur. J. 2014, 20, 223-231;
6. J. Iehl, J.-F. Nierengarten, A. Harriman, T. Bura, R. Ziessel, J. Am. Chem. Soc. 2012, 134, 988-998;
7. J. Iehl, M. Frasconi, H.-P. Jacquot de Rouville, N. Renaud, S. M. Dyar, N. L. Strutt, R. Carmieli, M. R. Wasielewski, M. A. Ratner, J.-F. Nierengarten, J. F. Stoddart, Chem. Sci. 2013, 4, 1462-1469.
8. P. J. Cragg, K. Sharma, Chem. Soc. Rev. 2012, 41, 597-607;
9. M. Xue, Y. Yang, X. Chi, Z. Zhang, F. Huang, Acc. Chem. Res. 2012, 45, 1294-1308;
10. T. Ogoshi, J. Inclusion Phenom. Macrocyclic Chem. 2012, 72, 247-262;
11. T. Ogoshi, T.-a. Yamagishi, Eur. J. Org. Chem. 2013, 2961-2975;
12. D. Cao, H. Meier, Asian J. Org. Chem. 2014, 3, 244-262;
13. T. Ogoshi, T. Yamagishi, Chem. Commun. 2014, 50, 4776-4787;
14. N. L. Strutt, H. Zhang, S. T. Schneebeli, J. F. Stoddart, Acc. Chem. Res. 2014, 47, 2631-2642.
15. I. Nierengarten, M. Nothisen, D. Sigwalt, T. Biellmann, M. Holler, J.-S. Remy, J.-F. Nierengarten, Chem. Eur. J. 2013, 19, 17552-17558;
16. I. Nierengarten, S. Guerra, M. Holler, L. Karmazin-Brelot, J. Barbera, R. Deschenaux, J.-F. Nierengarten, Eur. J. Org. Chem. 2013, 3675-3684;
17. I. Nierengarten, K. Buffet, M. Holler, S. P. Vincent, J.-F. Nierengarten, Tetrahedron Lett. 2013, 54, 2398-2402.
18. Z. Zhang, B. Xia, C. Han, Y. Yu, F. Huang, Org. Lett. 2010, 12, 3285-3287;
19. L. Liu, D. Cao, Y. Jin, H. Tao, Y. Kou, H. Meier, Org. Biomol. Chem. 2011, 9, 7007-7010.
20. M. Holler, N. Allenbach, J. Sonet, J.-F. Nierengarten, Chem. Commun. 2012, 48, 2576-2578.
21. N. L. Strutt, R. S. Forgan, J. M. Spruell, Y. Y. Botros, J. F. Stoddart, J. Am. Chem. Soc. 2011, 133, 5668-5671;
22. T. Ogoshi, Y. Nishida, T.-a. Yamagishi, Y. Nakamoto, Macromolecules 2010, 43, 7068-7072;
23. T. Ogoshi, D. Yamafuji, T. Aoki, T.-a. Yamagishi, Chem. Commun. 2012, 48, 6842-6844;
24. T. Ogoshi, D. Yamafuji, T. Aoki, K. Kitajima, T.-a. Yamagishi, Y. Hayashi, S. Kawauchi, Chem. Eur. J. 2012, 18, 7493-7500;
25. P. Wei, X. Yan, J. Li, Y. Ma, Y. Yao, F. Huang, Tetrahedron 2012, 68, 9179-9185;
26. T. Ogoshi, T. Aoki, R. Shiga, R. Iizuka, S. Ueda, K. Demachi, D. Yamafuji, H. Kayama, T.-a. Yamagishi, J. Am. Chem. Soc. 2012, 134, 20322-20325;
27. X.-Y. Hu, X. Wu, Q. Duan, T. Xiao, C. Lin, L. Wang, Org. Lett. 2012, 14, 4826-4829;
28. T. Ogoshi, D. Yamafuji, T.-a. Yamagishi, A. M. Brouwer, Chem. Commun. 2013, 49, 5468-5470;
29. C. Ke, N. L. Strutt, H. Li, X. Hou, K. J. Hartlieb, P. R. McGonigal, Z. Ma, J. Iehl, C. L. Stern, C. Cheng, Z. Zhu, N. A. Vermeulen, T. J. Meade, Y. Y. Botros, J. F. Stoddart, J. Am. Chem. Soc. 2013, 135, 17019-17030;
30. X. Hou, C. Ke, C. Cheng, N. Song, A. K. Blackburn, A. A. Sarjeant, Y. Y. Botros, Y.-W. Yang, J. F. Stoddart, Chem. Commun. 2014, 50, 6196-6199;
31. T. M. N. Trinh, I. Nierengarten, M. Holler, J.-L. Gallani, J.-F. Nierengarten, Chem. Eur. J. 2015, 21, 8019-8022.
32. V. Wittmann, R. Pieters, Chem. Soc. Rev. 2013, 42, 4492-44503;
33. Y. M. Chabre, R. Roy, Adv. Carbohydrate Chem. and Biochem. 2010, 63, 165-393;
34. M. Hartmann, T. K. Lindhorst, Eur. J. Org. Chem. 2011, 3583-3609;
35. S. Cecioni, A. Imberty, S. Vidal, Chem. Rev. 2015, 115, 525-561;
36. Y. Chen, A. Star, S. Vidal, Chem. Soc. Rev. 2013, 42, 4532-4542;
37. Y. M. Chabre, R. Roy, Chem. Soc. Rev. 2013, 42, 4657-4708;
38. M. Gingras, Y. M. Charbre, M. Roy, R. Roy, Chem. Soc. Rev. 2013, 42, 4823-4841;
39. A. Bernardi, J. Jiménez-Barbero, A. Casnati, C. De Castro, T. Darbre, F. Fieschi, J. Finne, H. Funken, K.-E. Jaeger, M. Lahmann, T. K. Lindhorst, M. Marradi, P. Messner, A. Molinaro, P. V. Murphy, C. Nativi, S. Oscarson, S. Penadés, F. Peri, R. J. Pieters, O. Renaudet, J.-L. Reymond, B. Richichi, J. Rojo, F. Sansone, C. Schäffer, W. B. Turnbull, T. Velasco-Torrijos, S. Vidal, S. P. Vincent, T. Wennekes, H. Zuilhof, A. Imberty, Chem. Soc. Rev. 2013, 42, 4709-4727;
40. I. Nierengarten, J.-F. Nierengarten, Chem. Asian J. 2014, 9, 1436-1444.
41. J. L. Jiménez Blanco, C. Ortiz Mellet, J. M. Garcia Fernandez, Chem. Soc. Rev. 2013, 42, 4518-4531. For examples see:
42. I. Deguise, D. Lagnoux, R. Roy, New J. Chem. 2007, 31, 1321-1331;
43. B. Gerland, A. Goudot, G. Pourceau, A. Meyer, S. Vidal, E. Souteyrand, J.-J. Vasseur, Y. Chevolot, F. Morvan, J. Org. Chem. 2012, 77, 7620-7626;
44. D. Ponader, P. Maffre, J. Aretz, D. Pussak, N. M. Ninnermann, S. Schmidt, P. H. Seeberger, C. Rademacher, G. U. Nienhaus, L. Hartmann, J. Am. Chem. Soc. 2014, 136, 2008-2016;
45. B. Thomas, M. Fiore, I. Bossu, P. Dumy, O. Renaudet, Beilstein J. Org. Chem. 2012, 8, 421-427.
46. A. Imberty, M. Wimmerova, E. P. Mitchell, N. Gilboa-Garber, Microbes Infect. 2004, 6, 221-229;
47. C. Chemani, A. Imberty, S. de Bentzman, P. Pierre, M. Wimmerová, B. P. Guery, K. Faure, Infect. Immun. 2009, 77, 2065-2075;
48. T. Eierhoff, B. Bastian, R. Thuenauer, J. Madl, A. Audfray, S. Aigal, S. Juillot, G. E. Rydell, S. Müller, S. de Bentzmann, A. Imberty, C. Fleck, W. Römer, Proc. Natl. Acad. Sci. USA 2014, 111, 12895-12900.
49. P. R. Ashton, S. R. L. Everitt, M. Gomez-Lopez, N. Jayaraman, J. F. Stoddart, Tetrahedron Lett. 1997, 38, 5691-5694;
50. A. Nelson, J. M. Belitsky, S. Vidal, C. S. Joiner, L. G. Baum, J. F. Stoddart, J. Am. Chem. Soc. 2004, 126, 11914-11922;
51. F. Coutrot, E. Busseron, J.-L. Montero, Org. Lett. 2008, 10, 753-756;
52. F. Coutrot, E. Busseron, Chem. Eur. J. 2008, 14, 4784-4787;
53. F. Coutrot, E. Busseron, Chem. Eur. J. 2009, 15, 5186-5190;
54. A. Fernandes, A. Viterisi, F. Coutrot, S. Potok, D. A. Leigh, V. Aucagne, S. Papot, Angew. Chem. Int. Ed. 2009, 48, 6443-6447;
55. Angew. Chem. 2009, 121, 6565-6569;
56. E. Busseron, C. Romuald, F. Coutrot, Chem. Eur. J. 2010, 16, 10062-10073;
57. R. Barat, T. Legigan, I. Tranoy-Opalinski, B. Renoux, E. Péraudeau, J. Clarhaut, P. Poinot, A. E. Fernandes, V. Aucagne, D. A. Leigh, S. Papot, Chem. Sci. 2015, 6, 2608-2613.
58. The yields of [2]rotaxane are influenced by the size of the peripheral substituents of the pillar[5]arene building block; for a systematic investigation, see:, R. Milev, A. Lopez-Pacheco, I. Nierengarten, T. M. N. Trinh, M. Holler, R. Deschenaux, J.-F. Nierengarten, Eur. J. Org. Chem. 2015, 479-485.
59. S. Cecioni, J.-P. Praly, S. E. Matthews, M. Wimmerova, A. Imberty, S. Vidal, Chem. Eur. J. 2012, 18, 6250-6263.
60. C. Sabin, E. P. Mitchell, M. Pokorna, C. Gautier, J.-P. Utille, M. Wimmerova, A. Imberty, FEBS Lett. 2006, 580, 982-987;
61. E. Mitchell, C. Houles, D. Sudakevitz, M. Wimmerova, C. Gautier, S. Pérez, A. M. Wu, N. Gilboa-Garber, A. Imberty, Nat. Struct. Biol. 2002, 9, 918-921.
62. K. Buffet, E. Guillon, M. Holler, J.-F. Nierengarten, A. Imberty, S. P. Vincent, Org. Biomol. Chem. 2015, 13, 6482-6492.
63. S. Cecioni, V. Oerthel, J. Iehl, M. Holler, D. Goyard, J.-P. Praly, A. Imberty, J.-F. Nierengarten, S. Vidal, Chem. Eur. J. 2011, 17, 3252-3261;
64. J.-L. Reymond, M. Bergmann, T. Darbre, Chem. Soc. Rev. 2013, 42, 4814-4822;
65. A. Novoa, T. Eierhoff, J. Topin, A. Varrot, S. Barluenga, A. Imberty, W. Römer, N. Winssinger, Angew. Chem. Int. Ed. 2014, 53, 8885-8889;
66. Angew. Chem. 2014, 126, 9031-9035;
67. F. Pertici, D. J. de Mol, J. Kemmink, R. J. Pieters, Chem. Eur. J. 2013, 19, 16923-16927.