Dipeptides as microporous materials

Angewandte Chemie - International Edition

Volumn 43, Issue 46, 2004, Pages 6308-6311

  Soldatov, Dmitriy V ^a   Moudrakovski, Igor L ^b   Ripmeester, John A ^b  

^a NIKOLAEV INSTITUTE OF INORGANIC CHEMISTRY   (Russian Federation)

^b NATIONAL RESEARCH COUNCIL CANADA   (Canada)

Author keywords

Chirality; Inclusion compounds; Microporosity; Peptides; Zeolites

Indexed keywords

HYDROGEN BONDS; MICROPOROUS MATERIALS; MOLECULAR STRUCTURE; SORPTION;

DIPEPTIDES; GAS SORPTION;

PROTEINS;

DIPEPTIDE DERIVATIVE; ZEOLITE;

ARTICLE; CHIRALITY; CRYSTAL STRUCTURE; GAS DIFFUSION; HYDROGEN BOND; NUCLEAR MAGNETIC RESONANCE; POROSITY; PROTEIN MOTIF; PROTEIN STABILITY; PROTEIN STRUCTURE; STRUCTURE ANALYSIS; X RAY POWDER DIFFRACTION;

ALANINE; DIPEPTIDES; MODELS, MOLECULAR; POROSITY; PROTEIN CONFORMATION; VALINE; X-RAY DIFFRACTION; XENON;

EID: 11144241037     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200460952     Document Type: Article

References (59)

1. a) J. Lipkowski in Inclusion Compounds, Vol. 1 (Eds. J. L. Atwood, J. E. D. Davies, D. D. MacNicol), Academic, London, 1984, pp. 59-103;
2. b) B. T. Ibragimov, S. A. Talipov, T. F. Aripov, J. Inclusion Phenom. Mol. Recognit. Chem. 1994, 17, 317-324;
3. c) A. T. Ung, D. Gizachew, R. Bishop, M. L. Scudder, I. G. Dance, D. C. Craig, J. Am. Chem. Soc. 1995, 117, 8745-8756;
4. d) D. V. Soldatov, J. A. Ripmeester, S. I. Shergina, I. E. Sokolov, A. S. Zanina, S. A. Gromilov, Yu. A. Dyadin, J. Am. Chem. Soc. 1999, 121, 4179-4188;
5. e) D. V. Soldatov, J. A. Ripmeester, Chem. Mater. 2000, 12, 1827-1839;
6. f) P. Sozzani, A. Comotti, R. Simonutti, T. Meersmann, J. W. Logan, A. Pines, Angew. Chem. 2000, 112, 2807-2810; Angew. Chem. Int. Ed. 2000, 39, 2695-2698;
7. f) P. Sozzani, A. Comotti, R. Simonutti, T. Meersmann, J. W. Logan, A. Pines, Angew. Chem. 2000, 112, 2807-2810; Angew. Chem. Int. Ed. 2000, 39, 2695-2698;
8. g) O. Kristiansson, L.-E. Tergenius, J. Chem. Soc. Dalton Trans. 2001, 1415-1420;
9. h) A. V. Nossov, D. V. Soldatov, J. A. Ripmeester, J. Am. Chem. Soc. 2001, 123, 3563-3568;
10. i) G. J. Halder, C. J. Kepert, B. Moubaraki, K. S. Murray, J. D. Cashion, Science 2002, 298, 1762-1765;
11. j) K. Uemura, S. Kitagawa, M. Kondo, K. Fukui, R. Kitaura, H.-C. Chang, T. Mizutani, Chem. Eur. J. 2002, 8, 3586-3600;
12. k) K. Seki, Phys. Chem. Chem. Phys. 2002, 4, 1968-1971;
13. l) T. Ueda, T. Eguchi, N. Nakamura, R. E. Wasylishen, J. Phys. Chem. B 2003, 107, 180-185;
14. m) R. Kitaura, K. Seki, G. Akiyama, S. Kitagawa, Angew. Chem. 2003, 115, 381; Angew. Chem. Int. Ed. 2003, 42, 428-431;
15. m) R. Kitaura, K. Seki, G. Akiyama, S. Kitagawa, Angew. Chem. 2003, 115, 381; Angew. Chem. Int. Ed. 2003, 42, 428-431;
16. n) E. B. Rusanov, V. V. Ponomareva, V. V. Komarchuk, H. Stoeckli-Evans, E. Fernandez-Ibañez, F. Stoeckli, J. Sieler, K. V. Domasevitch, Angew. Chem. 2003, 115, 2603-2605; Angew. Chem. Int. Ed. 2003, 42, 2499-2501;
17. n) E. B. Rusanov, V. V. Ponomareva, V. V. Komarchuk, H. Stoeckli-Evans, E. Fernandez-Ibañez, F. Stoeckli, J. Sieler, K. V. Domasevitch, Angew. Chem. 2003, 115, 2603-2605; Angew. Chem. Int. Ed. 2003, 42, 2499-2501;
18. o) L. Pan, M. B. Sander, X. Huang, J. Li, M. Smith, E. Bittner, B. Bockrath, J. K. Johnson, J. Am. Chem. Soc. 2004, 126, 1308-1309.
19. a) R. M. Barrer in Inclusion Compounds, Vol. 1 (Eds.: J. L. Atwood, J. E. D. Davies, D. D. MacNicol), Academic Press, London, 1984, pp. 191-248;
20. b) Nanoporous Materials III, Studies in Surface Science and Catalysis, Vol. 141 (Eds.: A. Sayari, M. Jaroniec), Elsevier, Amsterdam, 2002.
21. a) D. V. Soldatov, J. Inclusion Phenom. Mol. Recognit. Chem. 2004, 48, 3-9, and references therein;
22. b) D. V. Soldatov in Encyclopedia of Supramolecular Chemistry (Eds. J. L. Atwood, J. W. Steed), Marcel Dekker, New York, 2004, pp. 1302-1306, and references therein.
23. a) M. R. Ghadiri, J. R. Granja, R. A. Milligan, D. E. McRee, N. Khazanovich, Nature 1993, 366, 324-327;
24. b) S. McKim, J. F. Hinton, Biochim. Biophys. Acta 1994, 1193, 186-198;
25. c) D. Seebach, P. E. Ciceri, M. Overhand, B. Jaun, D. Rigo, L. Oberer, U. Hommel, R. Amstutz, H. Widmer, Helv. Chim. Acta 1996, 79, 2043-2067;
26. d) J. D. Hartgerink, T. D. Clark, M. R. Ghadiri, Chem. Eur. J. 1998, 4, 1367-1372;
27. e) M. Rechez, E. Gazit, Science 2003, 300, 625-627;
28. f) T.-L. Lau, K. J. Barnham, C. C. Curtain, C. L. Masters, F. Separovic, Aust. J. Chem. 2003, 56, 349-356.
29. a) K. Ogura, Yukagaku 1994, 43, 779-786 (in Japanese);
30. b) S. N. Mitra, E. Subramanian, Biopolymers 1994, 34, 1139-1143;
31. c) C.H. Görbitz, Acta Chem. Scand. 1998, 52, 1343-1349;
32. d) C. H. Görbitz, Acta Crystallogr. 2002, B58, 849-854.
33. Crystallizations of AV and VA were performed from distilled water without using a template. Crystals suitable for single-crystal XRD analyses were obtained by evaporation of 0.3 M solutions at 60°C. PXRD analyses indicated a total correspondence between the bulk products and the samples studied. The same single-crystal phase for each dipeptide, as confirmed by PXRD, was observed for the as-received samples (Sigma and ICN), solid products of fast crystallizations (evaporation in seconds at RT; evaporation over 2 h at 60°C), very slow crystallizations (evaporation over 2 months at RT), and for crystals exhaustively equilibrated with their supernatant aqueous solutions (8 months at RT).
34. 2. CCDC-238397 (AV) and CCDC 238398 (VA) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB21EZ, UK; fax: (+44)1223-336-033; or deposit@ ccdc.cam.ac.uk).
35. Low-temperature crystal structures of the compounds were reported: AV at 150 K (ref. [5d]) and VA at 120 K (ref. [9]).
36. C. H. Görbitz, E. Gundersen, Acta Crystallogr. 1996, C52, 1764-1767.
37. A. R. George, K. M. D. Harris, J. Mol. Graphics 1995, 13, 138-141.
38. Although the crystal structure of urea shows a chiral hexagonal structure, the channel is almost an ideal cylinder, with its center not deviating significantly from the sixfold crystallographic axis.
39. a) W. Yue, R. Bishop, M. L. Scudder, D. C. Craig, Chem. Lett. 1998, 803-804;
40. b) T. E. Gier, X. Bu, P. Feng, G. D. Stucky, Nature 1998, 395, 154-157;
41. c) J. S. Seo, D. Whang, H. Lee, S. I. Jun, J. Oh, Y. J. Jeon, K. Kim, Nature 2000, 404, 982-986;
42. d) C. J. Kepert, T. J. Prior, M. J. Rosseinsky, J. Am. Chem. Soc. 2000, 122, 5158-5168;
43. e) H.-Z. Shi, Y.-K. Shan, M.-Y. He, L.-Y. Dai, Y.-Y. Liu, L.-H. Weng, Acta Chim. Sin. 2003, 61, 711-714 (in Chinese);
44. f) P. Grosshans, A. Jouaiti, V. Bulach, J.-M. Planeix, M. W. Hosseini, J.-F. Nicoud, CrystEngComm 2003, 5, 414-416;
45. g) Y. V. Mironov, N. G. Naumov, K. A. Brylev, O. A. Efremova, V. E. Fedorov, K. Hegetschweiler, Angew. Chem. 2004, 116, 1317-1321; Angew. Chem. Int. Ed. 2004, 43, 1297-1300.
46. g) Y. V. Mironov, N. G. Naumov, K. A. Brylev, O. A. Efremova, V. E. Fedorov, K. Hegetschweiler, Angew. Chem. 2004, 116, 1317-1321; Angew. Chem. Int. Ed. 2004, 43, 1297-1300.
47. S. Kitagawa, M. Kondo, Bull. Chem. Soc. Jpn. 1998, 71, 1739-1753.
48. The diversity of zeolite structures results from the 16 identified "secondary structural units" which must be fitted together to give the combinations of channels and cavities which yield the repeat unit of the zeolite structures; see W. Meier, D. H. Olson, Atlas of Zeolite Structure Types 2nd ed., University Press, Cambridge, 1987; (the list of the units is given on p 5 therein).
49. 2; average diameter of the channel, 5.2(1)/5.1(1) Å.
50. The channel volumes were calculated from single-crystal XRD results by integration of the spatial figure composed of discs having diameters corresponding to the maximum-sized sphere that could be inscribed in the channel and centered on a given level along the crystallographic z axis.
51. 1 relaxation times of adsorbed xenon in the materials studied were found to be in the range of 50 to 80 s and care was taken to set the delays in the NMR experiments sufficiently long to ensure quantitative results. Equilibrium was reached typically in 2 h and the data were highly reproducable both when approaching equilbrium in the sorption or desorption modes. The sorption isotherms were approximated by a Langmuir equation, and the maximum sorption capacity and sorption constants were calculated as described in Ref. [1h].
52. D. V. Soldatov, I. L. Moudrakovski, C. I. Ratcliffe, R. Dutrisac, J. A. Ripmeester, Chem. Mater. 2003, 15, 4810-4818; (the sorption capacities of various sorbents are compared on p 4818 therein).
53. -1.
54. Inclusion Compounds (Eds.: J. L. Atwood, J. E. D. Davies, D. D. MacNicol), Academic, London, 1984.
55. a) C. H. Görbitz, Chem. Eur. J. 2001, 7, 5153-5159;
56. b) C. H. Görbitz, New J. Chem. 2003, 27, 1789-1793.
57. a) C. Landon, P. Berthault, F. Vovelle, H. Desvaux, Protein Sci. 2001, 10, 762-770;
58. b) B. M. Goodson, J. Magn. Reson. 2002, 155, 157-216;
59. c) S. M. Rubin, S. Y. Lee, E. J. Ruiz, A. Pines, D. E. Wemmer, J. Mol. Biol. 2002, 322, 425-440.