Cystinophanes, a novel family of aromatic-bridged cystine cyclic peptides: Synthesis, crystal structure, molecular recognition, and conformational studies

Journal of the American Chemical Society

Volumn 120, Issue 12, 1998, Pages 2695-2702

  Ranganathan, Darshan ^a   Haridas, V ^a   Karle, Isabella L ^b  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

^b NAVAL RESEARCH LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPEPTIDE; CYSTINOPHANE; PEPTIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; COMPLEX FORMATION; CONFORMATIONAL TRANSITION; CRYSTAL STRUCTURE; CYCLIZATION; MOLECULAR RECOGNITION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PEPTIDE SYNTHESIS; PROTEIN FAMILY;

EID: 0032054174     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9734915     Document Type: Article

References (52)

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34. For a recent overview on cyclophanes see: Vögtle, F. Cyclophane Chemistry; Wiley: Chichester, 1993. Diederich, F. Cyclophanes. In Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; Royal Society of Chemistry: Letchworth, UK, 1991. In Comprehensive Supramolecular Chemistry; Atwood, J. L., Davies, J. E. D., Macnicol, D. D., Vögtle, F., Eds.; Pergamon Press: New York, 1996; Vol. 2, Odashima, K., Koga, K., pp 143-209; Vögtle, F., Seel, C., Windscheif, P.-M., pp 211-265.
35. For a recent overview on cyclophanes see: Vögtle, F. Cyclophane Chemistry; Wiley: Chichester, 1993. Diederich, F. Cyclophanes. In Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; Royal Society of Chemistry: Letchworth, UK, 1991. In Comprehensive Supramolecular Chemistry; Atwood, J. L., Davies, J. E. D., Macnicol, D. D., Vögtle, F., Eds.; Pergamon Press: New York, 1996; Vol. 2, Odashima, K., Koga, K., pp 143-209; Vögtle, F., Seel, C., Windscheif, P.-M., pp 211-265.
36. For a recent overview on cyclophanes see: Vögtle, F. Cyclophane Chemistry; Wiley: Chichester, 1993. Diederich, F. Cyclophanes. In Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; Royal Society of Chemistry: Letchworth, UK, 1991. In Comprehensive Supramolecular Chemistry; Atwood, J. L., Davies, J. E. D., Macnicol, D. D., Vögtle, F., Eds.; Pergamon Press: New York, 1996; Vol. 2, Odashima, K., Koga, K., pp 143-209; Vögtle, F., Seel, C., Windscheif, P.-M., pp 211-265.
37. 2+2 cyclization product was also found to be the major product in the reaction of cystine dimethyl ester with adamantane template (Ranganathan, D.; Haridas, V.; Madhusudanan, K. P.; Roy, R.; Nagaraj, R.; John, G. B.; Sukhaswami, M. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 1105).
38. 2] afforded 25-membered macrocyclic peptides as the exclusive products through 1 + 1 cyclization with template dichlorides (Ranganathan, D.; Haridas, V. Unpublished results).
39. Ranganathan, D.; Haridas, V.; Madhusudanan, K. P.; Roy, R.; Nagaraj, R.; John, G. B. Unpublished results.
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41. Although several examples of acyclic receptors for dicarboxylic acids are reported (for example, see: Hosseini, M. W.; Lehn, J. M. J. Am. Chem. Soc. 1982, 104, 3525. Breslow, R.; Rajagopalan, R.; Schwartz, J. J. Am. Chem. Soc. 1981, 103, 2905. Kimura, E.; Sakonaka, A.; Yatsanami, T.; Kodami, M. J. Am. Chem. Soc. 1981, 103, 3041. Rebek, J., Jr.; Nemeth, D.; Ballester, P.; Lin, F. T. J. Am. Chem. Soc. 1987, 109, 3474. Tanaka, Y.; Kato, Y.; Aoyama, Y. J. Am. Chem. Soc. 1990, 112, 2807. Garcio-Tellado, F.; Geib, S. J.; Goswami, S.; Hamilton, A. D. J. Am. Chem. Soc. 1991, 113, 9265. Geib, S. J.; Vincent, C.; Fan, E.; Hamilton, A. D. Angew. Chem., Int. Ed. Engl. 1993, 32, 119. Karle, I. L.; Ranganathan, D.; Haridas, V. J. Am. Chem. Soc. 1997, 119, 2777), the reports on the cyclic receptors for dicarboxylic acids are still scarce (Garcia-Tellado, F.; Goswami, S.; Chang, S.-K.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1990, 112, 7393).
42. Although several examples of acyclic receptors for dicarboxylic acids are reported (for example, see: Hosseini, M. W.; Lehn, J. M. J. Am. Chem. Soc. 1982, 104, 3525. Breslow, R.; Rajagopalan, R.; Schwartz, J. J. Am. Chem. Soc. 1981, 103, 2905. Kimura, E.; Sakonaka, A.; Yatsanami, T.; Kodami, M. J. Am. Chem. Soc. 1981, 103, 3041. Rebek, J., Jr.; Nemeth, D.; Ballester, P.; Lin, F. T. J. Am. Chem. Soc. 1987, 109, 3474. Tanaka, Y.; Kato, Y.; Aoyama, Y. J. Am. Chem. Soc. 1990, 112, 2807. Garcio-Tellado, F.; Geib, S. J.; Goswami, S.; Hamilton, A. D. J. Am. Chem. Soc. 1991, 113, 9265. Geib, S. J.; Vincent, C.; Fan, E.; Hamilton, A. D. Angew. Chem., Int. Ed. Engl. 1993, 32, 119. Karle, I. L.; Ranganathan, D.; Haridas, V. J. Am. Chem. Soc. 1997, 119, 2777), the reports on the cyclic receptors for dicarboxylic acids are still scarce (Garcia-Tellado, F.; Goswami, S.; Chang, S.-K.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1990, 112, 7393).
43. Although several examples of acyclic receptors for dicarboxylic acids are reported (for example, see: Hosseini, M. W.; Lehn, J. M. J. Am. Chem. Soc. 1982, 104, 3525. Breslow, R.; Rajagopalan, R.; Schwartz, J. J. Am. Chem. Soc. 1981, 103, 2905. Kimura, E.; Sakonaka, A.; Yatsanami, T.; Kodami, M. J. Am. Chem. Soc. 1981, 103, 3041. Rebek, J., Jr.; Nemeth, D.; Ballester, P.; Lin, F. T. J. Am. Chem. Soc. 1987, 109, 3474. Tanaka, Y.; Kato, Y.; Aoyama, Y. J. Am. Chem. Soc. 1990, 112, 2807. Garcio-Tellado, F.; Geib, S. J.; Goswami, S.; Hamilton, A. D. J. Am. Chem. Soc. 1991, 113, 9265. Geib, S. J.; Vincent, C.; Fan, E.; Hamilton, A. D. Angew. Chem., Int. Ed. Engl. 1993, 32, 119. Karle, I. L.; Ranganathan, D.; Haridas, V. J. Am. Chem. Soc. 1997, 119, 2777), the reports on the cyclic receptors for dicarboxylic acids are still scarce (Garcia-Tellado, F.; Goswami, S.; Chang, S.-K.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1990, 112, 7393).
44. Although several examples of acyclic receptors for dicarboxylic acids are reported (for example, see: Hosseini, M. W.; Lehn, J. M. J. Am. Chem. Soc. 1982, 104, 3525. Breslow, R.; Rajagopalan, R.; Schwartz, J. J. Am. Chem. Soc. 1981, 103, 2905. Kimura, E.; Sakonaka, A.; Yatsanami, T.; Kodami, M. J. Am. Chem. Soc. 1981, 103, 3041. Rebek, J., Jr.; Nemeth, D.; Ballester, P.; Lin, F. T. J. Am. Chem. Soc. 1987, 109, 3474. Tanaka, Y.; Kato, Y.; Aoyama, Y. J. Am. Chem. Soc. 1990, 112, 2807. Garcio-Tellado, F.; Geib, S. J.; Goswami, S.; Hamilton, A. D. J. Am. Chem. Soc. 1991, 113, 9265. Geib, S. J.; Vincent, C.; Fan, E.; Hamilton, A. D. Angew. Chem., Int. Ed. Engl. 1993, 32, 119. Karle, I. L.; Ranganathan, D.; Haridas, V. J. Am. Chem. Soc. 1997, 119, 2777), the reports on the cyclic receptors for dicarboxylic acids are still scarce (Garcia-Tellado, F.; Goswami, S.; Chang, S.-K.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1990, 112, 7393).
45. Although several examples of acyclic receptors for dicarboxylic acids are reported (for example, see: Hosseini, M. W.; Lehn, J. M. J. Am. Chem. Soc. 1982, 104, 3525. Breslow, R.; Rajagopalan, R.; Schwartz, J. J. Am. Chem. Soc. 1981, 103, 2905. Kimura, E.; Sakonaka, A.; Yatsanami, T.; Kodami, M. J. Am. Chem. Soc. 1981, 103, 3041. Rebek, J., Jr.; Nemeth, D.; Ballester, P.; Lin, F. T. J. Am. Chem. Soc. 1987, 109, 3474. Tanaka, Y.; Kato, Y.; Aoyama, Y. J. Am. Chem. Soc. 1990, 112, 2807. Garcio-Tellado, F.; Geib, S. J.; Goswami, S.; Hamilton, A. D. J. Am. Chem. Soc. 1991, 113, 9265. Geib, S. J.; Vincent, C.; Fan, E.; Hamilton, A. D. Angew. Chem., Int. Ed. Engl. 1993, 32, 119. Karle, I. L.; Ranganathan, D.; Haridas, V. J. Am. Chem. Soc. 1997, 119, 2777), the reports on the cyclic receptors for dicarboxylic acids are still scarce (Garcia-Tellado, F.; Goswami, S.; Chang, S.-K.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1990, 112, 7393).
46. Although several examples of acyclic receptors for dicarboxylic acids are reported (for example, see: Hosseini, M. W.; Lehn, J. M. J. Am. Chem. Soc. 1982, 104, 3525. Breslow, R.; Rajagopalan, R.; Schwartz, J. J. Am. Chem. Soc. 1981, 103, 2905. Kimura, E.; Sakonaka, A.; Yatsanami, T.; Kodami, M. J. Am. Chem. Soc. 1981, 103, 3041. Rebek, J., Jr.; Nemeth, D.; Ballester, P.; Lin, F. T. J. Am. Chem. Soc. 1987, 109, 3474. Tanaka, Y.; Kato, Y.; Aoyama, Y. J. Am. Chem. Soc. 1990, 112, 2807. Garcio-Tellado, F.; Geib, S. J.; Goswami, S.; Hamilton, A. D. J. Am. Chem. Soc. 1991, 113, 9265. Geib, S. J.; Vincent, C.; Fan, E.; Hamilton, A. D. Angew. Chem., Int. Ed. Engl. 1993, 32, 119. Karle, I. L.; Ranganathan, D.; Haridas, V. J. Am. Chem. Soc. 1997, 119, 2777), the reports on the cyclic receptors for dicarboxylic acids are still scarce (Garcia-Tellado, F.; Goswami, S.; Chang, S.-K.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1990, 112, 7393).
47. Although several examples of acyclic receptors for dicarboxylic acids are reported (for example, see: Hosseini, M. W.; Lehn, J. M. J. Am. Chem. Soc. 1982, 104, 3525. Breslow, R.; Rajagopalan, R.; Schwartz, J. J. Am. Chem. Soc. 1981, 103, 2905. Kimura, E.; Sakonaka, A.; Yatsanami, T.; Kodami, M. J. Am. Chem. Soc. 1981, 103, 3041. Rebek, J., Jr.; Nemeth, D.; Ballester, P.; Lin, F. T. J. Am. Chem. Soc. 1987, 109, 3474. Tanaka, Y.; Kato, Y.; Aoyama, Y. J. Am. Chem. Soc. 1990, 112, 2807. Garcio-Tellado, F.; Geib, S. J.; Goswami, S.; Hamilton, A. D. J. Am. Chem. Soc. 1991, 113, 9265. Geib, S. J.; Vincent, C.; Fan, E.; Hamilton, A. D. Angew. Chem., Int. Ed. Engl. 1993, 32, 119. Karle, I. L.; Ranganathan, D.; Haridas, V. J. Am. Chem. Soc. 1997, 119, 2777), the reports on the cyclic receptors for dicarboxylic acids are still scarce (Garcia-Tellado, F.; Goswami, S.; Chang, S.-K.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1990, 112, 7393).
48. Although several examples of acyclic receptors for dicarboxylic acids are reported (for example, see: Hosseini, M. W.; Lehn, J. M. J. Am. Chem. Soc. 1982, 104, 3525. Breslow, R.; Rajagopalan, R.; Schwartz, J. J. Am. Chem. Soc. 1981, 103, 2905. Kimura, E.; Sakonaka, A.; Yatsanami, T.; Kodami, M. J. Am. Chem. Soc. 1981, 103, 3041. Rebek, J., Jr.; Nemeth, D.; Ballester, P.; Lin, F. T. J. Am. Chem. Soc. 1987, 109, 3474. Tanaka, Y.; Kato, Y.; Aoyama, Y. J. Am. Chem. Soc. 1990, 112, 2807. Garcio-Tellado, F.; Geib, S. J.; Goswami, S.; Hamilton, A. D. J. Am. Chem. Soc. 1991, 113, 9265. Geib, S. J.; Vincent, C.; Fan, E.; Hamilton, A. D. Angew. Chem., Int. Ed. Engl. 1993, 32, 119. Karle, I. L.; Ranganathan, D.; Haridas, V. J. Am. Chem. Soc. 1997, 119, 2777), the reports on the cyclic receptors for dicarboxylic acids are still scarce (Garcia-Tellado, F.; Goswami, S.; Chang, S.-K.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1990, 112, 7393).
49. Although several examples of acyclic receptors for dicarboxylic acids are reported (for example, see: Hosseini, M. W.; Lehn, J. M. J. Am. Chem. Soc. 1982, 104, 3525. Breslow, R.; Rajagopalan, R.; Schwartz, J. J. Am. Chem. Soc. 1981, 103, 2905. Kimura, E.; Sakonaka, A.; Yatsanami, T.; Kodami, M. J. Am. Chem. Soc. 1981, 103, 3041. Rebek, J., Jr.; Nemeth, D.; Ballester, P.; Lin, F. T. J. Am. Chem. Soc. 1987, 109, 3474. Tanaka, Y.; Kato, Y.; Aoyama, Y. J. Am. Chem. Soc. 1990, 112, 2807. Garcio-Tellado, F.; Geib, S. J.; Goswami, S.; Hamilton, A. D. J. Am. Chem. Soc. 1991, 113, 9265. Geib, S. J.; Vincent, C.; Fan, E.; Hamilton, A. D. Angew. Chem., Int. Ed. Engl. 1993, 32, 119. Karle, I. L.; Ranganathan, D.; Haridas, V. J. Am. Chem. Soc. 1997, 119, 2777), the reports on the cyclic receptors for dicarboxylic acids are still scarce (Garcia-Tellado, F.; Goswami, S.; Chang, S.-K.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1990, 112, 7393).
50. Carboxylates being charged hydrogen-bond acceptors offer an additional advantage and exhibit increasing binding strength with amide NHs. (Kelly, T. R.; Kim, M. H. J. Am. Chem. Soc. 1994, 116, 7072. Fan, E.; Van Arman, S. A.; Kincaid, S.; Hamilton, A. D. J. Am. Chem. Soc. 1993, 115, 369.)
51. Carboxylates being charged hydrogen-bond acceptors offer an additional advantage and exhibit increasing binding strength with amide NHs. (Kelly, T. R.; Kim, M. H. J. Am. Chem. Soc. 1994, 116, 7072. Fan, E.; Van Arman, S. A.; Kincaid, S.; Hamilton, A. D. J. Am. Chem. Soc. 1993, 115, 369.)
52. max is the chemical shift when the receptor is entirely bound (Kelly, T. R.; Kim, M. H. J. Am. Chem. Soc. 1994, 116, 7072 and references therein).