Enantiopure Peptide-Functionalized Metal-Organic Frameworks

Journal of the American Chemical Society

Volumn 137, Issue 29, 2015, Pages 9409-9416

  Bonnefoy, Jonathan ^a   Legrand, Alexandre ^a   Quadrelli, Elsje Alessandra ^a   Canivet, Jérôme ^a   Farrusseng, David ^a  

^a UNIVERSITÉ LYON 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CONDENSATION REACTIONS; CRYSTALLINE MATERIALS; KETONES; ORGANOMETALLICS;

ALDOL REACTIONS; ASYMMETRIC CATALYSIS; FUNCTIONALIZED; HYBRID SOLIDS; METAL ORGANIC FRAMEWORK; MICROWAVE ASSISTED; OLIGOPEPTIDES; POSTSYNTHETIC MODIFICATION;

PEPTIDES;

AMINO ACID; GLYCINE; METAL ORGANIC FRAMEWORK; OLIGOPEPTIDE; ORGANIC COMPOUND; POLYPEPTIDE; PROLINE DERIVATIVE; DIPEPTIDE; KETONE; ORGANOMETALLIC COMPOUND;

ALDOL REACTION; ARTICLE; ASYMMETRIC CATALYSIS; ENANTIOSELECTIVITY; MICROWAVE IRRADIATION; MOLECULAR RECOGNITION; REACTION TIME; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; MICROWAVE RADIATION; STEREOISOMERISM; SYNTHESIS;

AMINO ACIDS; CATALYSIS; DIPEPTIDES; KETONES; MICROWAVES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM;

EID: 84938371551     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b05327     Document Type: Article

References (100)

1. Gu, Z.-Y.; Park, J.; Raiff, A.; Wei, Z.; Zhou, H.-C. ChemCatChem 2014, 6, 67 10.1002/cctc.201300493
2. Dhakshinamoorthy, A.; Opanasenko, M.; Cejka, J.; Garcia, H. Catal. Sci. Technol. 2013, 3, 2509 10.1039/c3cy00350g
3. Yoon, M.; Srirambalaji, R.; Kim, K. Chem. Rev. 2012, 112, 1196 10.1021/cr2003147
4. Liu, Y.; Xuan, W.; Cui, Y. Adv. Mater. 2010, 22, 4112 10.1002/adma.201000197
5. Corma, A.; Garcia, H.; Llabres i Xamena, F. X. L. I. Chem. Rev. 2010, 110, 4606 10.1021/cr9003924
6. Morris, R. E.; Bu, X. Nat. Chem. 2010, 2, 353 10.1038/nchem.628
7. Ma, L.; Abney, C.; Lin, W. Chem. Soc. Rev. 2009, 38, 1248 10.1039/b807083k
8. Heitbaum, M.; Glorius, F.; Escher, I. Angew. Chem., Int. Ed. 2006, 45, 4732 10.1002/anie.200504212
9. Lin, W. Top. Catal. 2010, 53, 869 10.1007/s11244-010-9519-3
10. Liu, J.; Chen, L.; Cui, H.; Zhang, J.; Zhang, L.; Su, C.-Y. Chem. Soc. Rev. 2014, 43, 6011 10.1039/C4CS00094C
11. Kudo, A.; Miseki, Y. Chem. Soc. Rev. 2009, 38, 253 10.1039/B800489G
12. Gomes Silva, C.; Luz, I.; Llabres i Xamena, F. X.; Corma, A.; Garcia, H. Chem.-Eur. J. 2010, 16, 11133 10.1002/chem.200903526
13. Wang, C.; Xie, Z.; deKrafft, K. E.; Lin, W. J. Am. Chem. Soc. 2011, 133, 13445 10.1021/ja203564w
14. Fateeva, A.; Chater, P. A.; Ireland, C. P.; Tahir, A. A.; Khimyak, Y. Z.; Wiper, P. V.; Darwent, J. R.; Rosseinsky, M. J. Angew. Chem., Int. Ed. 2012, 51, 7440 10.1002/anie.201202471
15. Wang, J.-L.; Wang, C.; Lin, W. ACS Catal. 2012, 2, 2630 10.1021/cs3005874
16. Wu, P.; He, C.; Wang, J.; Peng, X.; Li, X.; An, Y.; Duan, C. J. Am. Chem. Soc. 2012, 134, 14991 10.1021/ja305367j
17. Pullen, S.; Fei, H.; Orthaber, A.; Cohen, S. M.; Ott, S. J. Am. Chem. Soc. 2013, 135, 16997 10.1021/ja407176p
18. Sun, D.; Fu, Y.; Liu, W.; Ye, L.; Wang, D.; Yang, L.; Fu, X.; Li, Z. Chem.-Eur. J. 2013, 19, 14279 10.1002/chem.201301728
19. Wang, S.; Yao, W.; Lin, J.; Ding, Z.; Wang, X. Angew. Chem., Int. Ed. 2014, 53, 1034 10.1002/anie.201309426
20. Zhang, T.; Lin, W. Chem. Soc. Rev. 2014, 43, 5982 10.1039/C4CS00103F
21. Lin, W. B. J. Solid State Chem. 2005, 178, 2486 10.1016/j.jssc.2005.06.013
22. Vaidhyanathan, R.; Bradshaw, D.; Rebilly, J.-N.; Barrio, J. P.; Gould, J. A.; Berry, N. G.; Rosseinsky, M. J. Angew. Chem., Int. Ed. 2006, 45, 6495 10.1002/anie.200602242
23. Lin, W. MRS Bull. 2007, 32, 544 10.1557/mrs2007.104
24. Bao, X.; Broadbelt, L. J.; Snurr, R. Q. Mol. Simul. 2009, 35, 50 10.1080/08927020802422064
25. Nickerl, G.; Henschel, A.; Gruenker, R.; Gedrich, K.; Kaskel, S. Chem. Ing. Tech. 2011, 83, 90 10.1002/cite.201000188
26. Padmanaban, M.; Mueller, P.; Lieder, C.; Gedrich, K.; Gruenker, R.; Bon, V.; Senkovska, I.; Baumgaertner, S.; Opelt, S.; Paasch, S.; Brunner, E.; Glorius, F.; Klemm, E.; Kaskel, S. Chem. Commun. 2011, 47, 12089 10.1039/c1cc14893a
27. Moghadam, P. Z.; Dueren, T. J. Phys. Chem. C 2012, 116, 20874 10.1021/jp3056637
28. Suh, K.; Yutkin, M. P.; Dybtsev, D. N.; Fedin, V. P.; Kim, K. Chem. Commun. 2012, 48, 513 10.1039/C1CC16209H
29. Huang, K.; Dong, X.; Ren, R.; Jin, W. AIChE J. 2013, 59, 4364 10.1002/aic.14194
30. Zhang, M.; Pu, Z.-J.; Chen, X.-L.; Gong, X.-L.; Zhu, A.-X.; Yuan, L.-M. Chem. Commun. 2013, 49, 5201 10.1039/c3cc41966e
31. Lee, T.; Liu, Z. X.; Lee, H. L. Cryst. Growth Des. 2011, 11, 4146 10.1021/cg200710p
32. Khoshaman, A. H.; Bahreyni, B. Sens. Actuators, B 2012, 162, 114 10.1016/j.snb.2011.12.046
33. Kreno, L. E.; Leong, K.; Farha, O. K.; Allendorf, M.; Van Duyne, R. P.; Hupp, J. T. Chem. Rev. 2012, 112, 1105 10.1021/cr200324t
34. Wanderley, M. M.; Wang, C.; Wu, C.-D.; Lin, W. J. Am. Chem. Soc. 2012, 134, 9050 10.1021/ja302110d
35. Davydovskaya, P.; Pohle, R.; Tawil, A.; Fleischer, M. Sens. Actuators, B 2013, 187, 142 10.1016/j.snb.2012.10.023
36. Gong, Y.-N.; Jiang, L.; Lu, T.-B. Chem. Commun. 2013, 49, 11113 10.1039/c3cc46530f
37. Jin, Z.; He, H.; Zhao, H.; Borjigin, T.; Sun, F.; Zhang, D.; Zhu, G. Dalton Trans. 2013, 42, 13335 10.1039/c3dt51414e
38. Lee, T.; Lee, H. L.; Tsai, M. H.; Cheng, S.-L.; Lee, S.-W.; Hu, J.-C.; Chen, L.-T. Biosens. Bioelectron. 2013, 43, 56 10.1016/j.bios.2012.11.014
39. Long, Z.; Jia, J.; Wang, S.; Kou, L.; Hou, X.; Sepaniak, M. J. Microchem. J. 2013, 110, 764 10.1016/j.microc.2013.08.013
40. Zhang, Y.; Chen, Y.; Zhang, Y.; Cong, H.; Fu, B.; Wen, S.; Ruan, S. J. Nanopart. Res. 2013, 15, 2014
41. Zhu, X.; Zheng, H.; Wei, X.; Lin, Z.; Guo, L.; Qiu, B.; Chen, G. Chem. Commun. 2013, 49, 1276 10.1039/c2cc36661d
42. Kumar, P.; Kumar, P.; Bharadwaj, L. M.; Paul, A. K.; Deep, A. Inorg. Chem. Commun. 2014, 43, 114 10.1016/j.inoche.2014.02.022
43. Li, H.; Feng, X.; Guo, Y.; Chen, D.; Li, R.; Ren, X.; Jiang, X.; Dong, Y.; Wang, B. Sci. Rep. 2014, 4, 4366 10.1038/srep04366
44. Liu, D.; Lu, K.; Poon, C.; Lin, W. Inorg. Chem. 2014, 53, 1916 10.1021/ic402194c
45. Hu, Z.; Deibert, B. J.; Li, J. Chem. Soc. Rev. 2014, 43, 5815 10.1039/C4CS00010B
46. Lillerud, K. P.; Olsbye, U.; Tilset, M. Top. Catal. 2010, 53, 859 10.1007/s11244-010-9518-4
47. Wu, C. D.; Li, L.; Shi, L. X. Dalton Trans. 2009, 6790 10.1039/b823335g
48. Wang, M.; Xie, M. H.; Wu, C. D.; Wang, Y. G. Chem. Commun. 2009, 2396 10.1039/b823323c
49. Rabone, J.; Yue, Y. F.; Chong, S. Y.; Stylianou, K. C.; Bacsa, J.; Bradshaw, D.; Darling, G. R.; Berry, N. G.; Khimyak, Y. Z.; Ganin, A. Y.; Wiper, P.; Claridge, J. B.; Rosseinsky, M. J. Science 2010, 329, 1053 10.1126/science.1190672
50. Mantion, A.; Massuger, L.; Rabu, P.; Palivan, C.; McCusker, L. B.; Taubert, A. J. Am. Chem. Soc. 2008, 130, 2517 10.1021/ja0762588
51. Tanabe, K. K.; Cohen, S. M. Chem. Soc. Rev. 2011, 40, 498 10.1039/C0CS00031K
52. Cohen, S. M. Chem. Rev. 2012, 112, 970 10.1021/cr200179u
53. Lun, D. J.; Waterhouse, G. I. N.; Telfer, S. G. J. Am. Chem. Soc. 2011, 133, 5806 10.1021/ja202223d
54. Kutzscher, C.; Hoffmann, H. C.; Krause, S.; Stoeck, U.; Senkovska, I.; Brunner, E.; Kaskel, S. Inorg. Chem. 2015, 54, 1003 10.1021/ic502380q
55. Gedye, R.; Smith, F.; Westaway, K.; Ali, H.; Baldisera, L.; Laberge, L.; Rousell, J. Tetrahedron Lett. 1986, 27, 279 10.1016/S0040-4039(00)83996-9
56. Leonelli, C.; Mason, T. J. Chem. Eng. Process. 2010, 49, 885 10.1016/j.cep.2010.05.006
57. Lidstrom, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225 10.1016/S0040-4020(01)00906-1
58. Pedersen, S. L.; Tofteng, A. P.; Malik, L.; Jensen, K. J. Chem. Soc. Rev. 2012, 41, 1826 10.1039/C1CS15214A
59. Larhed, M.; Moberg, C.; Hallberg, A. Acc. Chem. Res. 2002, 35, 717 10.1021/ar010074v
60. Nehlig, E.; Milosevic, I.; Motte, L.; Guenin, E. Curr. Org. Chem. 2013, 17, 528
61. Kim, M.; Garibay, S. J.; Cohen, S. M. Inorg. Chem. 2011, 50, 729 10.1021/ic102436b
62. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; 2 nd ed.; John Wiley and Sons, Inc.: Hoboken, NJ, 1991.
63. Carganico, S.; Papini, A. M. In Amino Acids, Peptides and Proteins in Organic Chemistry; Hughes, A. B., Ed.; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2010; p 313.
64. Hojo, K.; Shinozaki, N.; Hidaka, K.; Tsuda, Y.; Fukumori, Y.; Ichikawa, H.; Wade, J. D. Amino Acids 2014, 46, 2347 10.1007/s00726-014-1779-y
65. Savonnet, M.; Farrusseng, D. Novel organic/inorganic hybrid material ihm-2, and methods for manufacturing same. PCT Appl. WO2011048284, April 28, 2011.
66. Barthelet, K.; Marrot, J.; Ferey, G.; Riou, D. Chem. Commun. 2004, 5) 520 10.1039/b312589k
67. Schubert, M.; Müller, U.; Marx, S. Organometallic framework materials having a hexagonal-trigonal structure based on aluminum, iron, and chromium, and a dicarboxylic acid. PCT Appl. WO2008129051, September 11, 2009.
68. Fateeva, A.; Horcajada, P.; Devic, T.; Serre, C.; Marrot, J.; Greneche, J. M.; Morcrette, M.; Tarascon, J. M.; Maurin, G.; Ferey, G. Eur. J. Inorg. Chem. 2010, 2010, 3789 10.1002/ejic.201000486
69. Volkringer, C.; Meddouri, M.; Loiseau, T.; Guillou, N.; Marrot, J.; Ferey, G.; Haouas, M.; Taulelle, F.; Audebrand, N.; Latroche, M. Inorg. Chem. 2008, 47, 11892 10.1021/ic801624v
70. Savonnet, M.; Bazer-Bachi, D.; Bats, N.; Perez-Pellitero, J.; Jeanneau, E.; Lecocq, V.; Pinel, C.; Farrusseng, D. J. Am. Chem. Soc. 2010, 132, 4518 10.1021/ja909613e
71. Ferey, G.; Mellot-Draznieks, C.; Serre, C.; Millange, F.; Dutour, J.; Surble, S.; Margiolaki, I. Science 2005, 309, 2040
72. Latroche, M.; Surble, S.; Serre, C.; Mellot-Draznieks, C.; Llewellyn, P. L.; Lee, J.-H.; Chang, J.-S.; Jhung, S. H.; Ferey, G. Angew. Chem., Int. Ed. 2006, 45, 8227 10.1002/anie.200600105
73. Hartmann, M.; Fischer, M. Microporous Mesoporous Mater. 2012, 164, 38 10.1016/j.micromeso.2012.06.044
74. Serra-Crespo, P.; Ramos-Fernandez, E. V.; Gascon, J.; Kapteijn, F. Chem. Mater. 2011, 23, 2565 10.1021/cm103644b
75. Kandiah, M.; Nilsen, M. H.; Usseglio, S.; Jakobsen, S.; Olsbye, U.; Tilset, M.; Larabi, C.; Quadrelli, E. A.; Bonino, F.; Lillerud, K. P. Chem. Mater. 2010, 22, 6632 10.1021/cm102601v
76. Merrifield, B. Methods Enzymol. 1997, 289, 3
77. Merrifield, R. B. Angew. Chem., Int. Ed. Engl. 1985, 24, 799 10.1002/anie.198507993
78. Montalbetti, C.; Falque, V. Tetrahedron 2005, 61, 10827 10.1016/j.tet.2005.08.031
79. Hintz, H.; Wuttke, S. Chem. Commun. 2014, 50, 11472 10.1039/C4CC02650K
80. Canivet, J.; Aguado, S.; Bergeret, G.; Farrusseng, D. Chem. Commun. 2011, 47, 11650 10.1039/c1cc15541e
81. Frerot, E.; Coste, J.; Pantaloni, A.; Dufour, M. N.; Jouin, P. Tetrahedron 1991, 47, 259 10.1016/S0040-4020(01)80922-4
82. Coste, J.; Frerot, E.; Jouin, P. J. Org. Chem. 1994, 59, 2437 10.1021/jo00088a027
83. Mukaiyama, T. Angew. Chem., Int. Ed. Engl. 1979, 18, 707 10.1002/anie.197907073
84. Volkringer, C.; Cohen, S. M. Angew. Chem., Int. Ed. 2010, 49, 4644 10.1002/anie.201001527
85. Kim, M.; Cahill, J. F.; Su, Y.; Prather, K. A.; Cohen, S. M. Chem. Sci. 2012, 3, 126 10.1039/C1SC00394A
86. Zhu, W.; He, C.; Wu, P.; Wu, X.; Duan, C. Dalton Trans. 2012, 41, 3072 10.1039/c2dt12153k
87. Kuhnert, N. Angew. Chem., Int. Ed. 2002, 41, 1863 10.1002/1521-3773(20020603)41:11<1863::AID-ANIE1863>3.0.CO;2-L
88. de la Hoz, A.; Diaz-Ortiz, A.; Moreno, A. Chem. Soc. Rev. 2005, 34, 164 10.1039/b411438h
89. de la Hoz, A.; Diaz-Ortiz, A.; Moreno, A. J. Microw. Power Electromagn. Energy 2007, 41, 44
90. Dudley, G. B.; Stiegman, A. E.; Rosana, M. R. Angew. Chem., Int. Ed. 2013, 52, 7918 10.1002/anie.201301539
91. Kappe, C. O. Angew. Chem., Int. Ed. 2013, 52, 7924 10.1002/anie.201304368
92. Kappe, C. O.; Pieber, B.; Dallinger, D. Angew. Chem., Int. Ed. 2013, 52, 1088 10.1002/anie.201204103
93. MacMillan, D. S.; Murray, J.; Sneddon, H. F.; Jamieson, C.; Watson, A. J. B. Green Chem. 2013, 15, 596 10.1039/c2gc36900a
94. Perreux, L.; Loupy, A. Tetrahedron 2001, 57, 9199 10.1016/S0040-4020(01)00905-X
95. Kappe, C. O. Chem. Soc. Rev. 2013, 42, 4977 10.1039/c3cs00010a
96. Doherty, S.; Knight, J. G.; McRae, A.; Harrington, R. W.; Clegg, W. Eur. J. Org. Chem. 2008, 2008, 1759 10.1002/ejoc.200700922
97. He, L.; Tang, Z.; Cun, L. F.; Mi, A. Q.; Jiang, Y. Z.; Gong, L. Z. Tetrahedron 2006, 62, 346 10.1016/j.tet.2005.09.061
98. List, B.; Lerner, R. A.; Barbas, C. F. J. Am. Chem. Soc. 2000, 122, 2395 10.1021/ja994280y
99. Maleev, V. I.; Gugkaeva, Z. T.; Moskalenko, M. A.; Tsaloev, A. T.; Lyssenko, K. A. Russ. Chem. Bull. 2009, 58, 1903 10.1007/s11172-009-0259-0
100. Liu, B.; Yang, F.; Zou, Y.; Peng, Y. J. Chem. Eng. Data 2014, 59, 1476 10.1021/je4010239