Optically active cyclic hexapeptides with covalently attached pyrene probes: Selective alkaline earth metal ion recognition using excimer emission

Organic Letters

Volumn 4, Issue 5, 2002, Pages 683-686

  Strauss, Jörg ^a   Daub, Jörg ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALINE EARTH METAL; CALCIUM; CYCLOPEPTIDE; DIAGNOSTIC AGENT; FLUORESCENT DYE; OLIGOPEPTIDE; PYRENE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; METABOLISM; MOLECULAR PROBE; OPTICAL ROTATION; SPECTROFLUOROMETRY; TITRIMETRY;

CALCIUM; FLUORESCENT DYES; METALS, ALKALINE EARTH; MODELS, MOLECULAR; MOLECULAR PROBES; OLIGOPEPTIDES; OPTICAL ROTATION; PEPTIDES, CYCLIC; PYRENES; SPECTROMETRY, FLUORESCENCE; TITRIMETRY;

EID: 0037035090     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0170354     Document Type: Article

References (50)

1. (a) Haubner, R.; Finsinger, D.; Kessler, H. Angew. Chem. 1997, 109, 1440-1456.
2. (b) Hu, B.; Finsinger, D.; Peter, K.; Guttenberg, Z.; Bärmann, M.; Kessler, H.; Escherich, A.; Moroder, L.; Böhm, J.; Baumeister, W.; Sui, S.; Sackmann, E. Biochemistry 2000, 39, 12284-12294.
3. (a) Schnur, J. M. Science 1993, 262, 1669-1676.
4. (b) Ghadiri, M. R.; Granja, J. R.; Milligan, R. A.; McRee, D. E.; Khazanovich, N. Nature 1993, 366, 324-327.
5. (a) Leipert, D.; Nopper, D.; Bauser, M.; Gauglitz, G.; Jung, G. Angew. Chem. 1998, 110, 3503-3505.
6. (b) Chiari, M.; Desperati, V.; Manera, E.; Longhi, R. Anal. Chem. 1998, 70, 4967-4973.
7. Kubik, S.; Goddard, R.; Kirchner, R.; Nolting, D.; Seidel, J. Angew. Chem. 2001, 113, 2122-2725.
8. (a) Kubik, S. J. Am. Chem. Soc. 1999, 121, 5846-5855.
9. (b) Kimura, S.; Ozeki, E.; Imanishi, Y. Biopolymers 1989, 28, 1235-1246.
10. (c) Nishino, N.; Shiroishi, T.; Muraoka, T.; Fujimoto, T. Chem. Lett. 1992, 665-668.
11. (a) Mihara, H.; Hayashida, J.; Hasegawa, H.; Ogawa, H. I.; Fujimoto, T.; Nishino, N. J. Chem. Soc., Perkin Trans. 2 1997, 517-522.
12. (b) Jones, G., II; Vullev, V. I. Org. Lett. 2001, 3, 2457-2461.
13. (c) Buranaprapuk, A.; Kumar, C. V.; Jockusch, S.; Turro, N. J. Tetrahedron 2000, 56, 7019-7025
14. (d) Clark, I.; Brown, C.; Sikorska-Walker, M.; MacManus, J.; Szabo, A. Anal. Chem. 1993, 213, 296-302.
15. (e) Arai, T.; Die, Y.; Tanaka, Y.; Fujimoto, T.; Nishino, N. Chem. Lett. 1995, 381-382.
16. (f) Sisido, M.; Tanaka, R.; Inai, Y.; Imanishi, Y. J. Am. Chem. Soc. 1989, 111, 6790-6796.
17. (g) Daugherty, D. L.; Gellman, S. H. J. Am. Chem. Soc. 1999, 121, 4325-4333.
18. (a) Pap, E.; van den Berg, P.; Borst, J.; Visser, A. J. Biol. Chem. 1995, 270, 1254-1260.
19. (b) Ueda, T.; Kimura, S.; Imanishi, Y. J. Chem. Soc., Perkin Trans. 2 1995, 359-363.
20. (a) Kataoka, H.; Hanawa, T.; Katagi, T. Chem. Pharm. Bull. 1992. 40, 570-574.
21. (b) Kimura, S.; Imanishi, Y. Biopolymers 1984, 23, 563-573.
22. (a) Xie, P.; Diem, M. J. Am. Chem. Soc. 1995, 117, 429-437.
23. (b) Ozeki, E.; Kimura, S.; Imanishi, Y. Int. J. Pept. Protein Res. 1989, 34, 111-117.
24. Egusa, S.; Sisido, M.; Imanishi, Y. Macromolecules 1985, 18, 882-889.
25. (a) Burk, M.; Feaster, J.; Nugent, W.; Harlow, R. J. Am. Chem. Soc. 1993, 115, 10125-10138.
26. (b) Aguado, G.; Alvarez-Larena, A.; Illa, O.; Moglioni, A.; Ortuno, R. Tetrahedron: Asymmetry 2001, 12, 25-28.
27. (c) Debenham, S.; Cossrow, J.; Toone, E. J. Org. Chem. 1999, 64, 9153-9163.
28. Soleilhac, J.-M.; Cornille, F.; Martin, L.; Lenoir, C.; Fournie-Zaluski, M.-C.; Roques, B. Anal. Biochem. 1996, 241, 120-127.
29. Dechantsreiter, M. A.; Planker, E.; Mathä, B.; Lohof, E.; Hölzemann, G.; Jonczyk, A.; Goodman, S. L.; Kessler, H. J. Med. Chem. 1999, 42, 3033-3040.
30. D-Pya = (R)-α-amino-1-pyrenepropanoic acid
31. (a) Boger, D. L.; Ledeboer, M. W.; Kume, M.; Searcey, M.; Jin, Q. J. Am. Chem. Soc. 1999, 121, 11375-11383.
32. (b) Ehrlich, A.; Heyne, H.-U.; Winter, R.; Beyermann, M.; Haber, H.; Carpino, L. A.; Bienen, M. J. Org. Chem. 1996, 61, 8831-8838.
33. 1H NMR, HR-MS or elemental analysis, IR, melting point, UV/vis spectroscopy, and angle of rotation.
34. Förster, T.; Kasper, K. Z. Elektrochem. 1955, 59, 976-980.
35. Only the longest wavelength bands and their molar extinction coefficients of the vibrationally split transitions are given.
36. -5 M.
37. Yamauchi, A.; Hayashita, T.; Kato, A.; Nishizawa, S.; Watanabe, M.; Teramae, N. Anal. Chem. 2000, 72, 5841-5846.
38. Logarithmic complexation constants (log K) are estimated numerically by the computer program HypNMR. Errors are valued with 15%. For details on HypNMR, see: Alderighi, L.; Bianchi, A.; Biondi, L.; Calabi, L.; De Miranda, M.; Gans, P.; Ghelli, S.; Losi, P.; Paleari, L.; Sabatini, A.; Vacca, A. J. Chem. Soc., Perkin Trans. 2 1999, 2741-2745.
39. (a) Yang, J.-S.; Lin, C.-S.; Hwang, C.-Y. Org. Lett. 2001, 3, 889-892.
40. (b) Monahan, C.; Bien, J,; Smith, B. Chem. Commun. 1998, 431-432.
41. (c) Aoki, I.; Kawabata, H.; Nakashima, K.; Shinkai, S. J. Chem. Soc., Chem. Commun. 1991, 1771-1773.
42. (d) Nishjzawa, S.; Watanabe, M.; Uchida, T.; Teramae, N. J. Chem. Soc., Perkin Trans. 2 1999, 141-143.
43. (e) Suzuki, Y.; Morozumi, T.; Nakamura, H.; Shimomura, M.; Hayashita, T.; Bartsh, R. A. J. Phys. Chem. 1998, 102, 7910-7917.
44. (a) Hori, K.; Kushick, J. N.; Weinstein, H. Biopolymers 1988, 27, 1865-1886.
45. (b) Varughese, K. I.; Aimoto, S.; Kartha, G. Int. J. Pept. Protein Res. 1986, 27, 118-123.
46. Wavefunction, Inc., 18401 Von Karmann Ave., Suite 370, Irvine, CA 92612.
47. Winnik, F. Chem. Rev. 1993, 93, 587-614.
48. (a) de Silva, A. P.; Gunaratne, H. Q. N.; Gunnlaugson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 7, 1515-1566.
49. (b) Westermeier, C.; Gallmeier, H.-C.; Komma, M.; Daub, J. Chem. Commun. 1999, 2427-2428.
50. (c) Beer, G.; Niederalt, C.; Grimme, S.; Daub, J. Angew. Chem. 2000, 112, 3385-3388.