Helical chirality induction in zinc bilindiones by amino acid esters and amines

Journal of Organic Chemistry

Volumn 63, Issue 24, 1998, Pages 8769-8784

  Mizutani, Tadashi ^a   Yagi, Shigeyuki ^b   Honmaru, Atsushi ^a   Murakami, Shinji ^b   Furusyo, Masaru ^c   Takagishi, Toru ^b   Ogoshi, Hisanobu ^a,d  

^a KYOTO UNIVERSITY   (Japan)

^b Osaka Prefecture University   (Japan)

^c SUMITOMO ELECTRIC INDUSTRIES LTD   (Japan)

^d FUKUI NATIONAL COLLEGE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,19 BILINDIONE DERIVATIVE; AMINE; AMINO ACID DERIVATIVE; UNCLASSIFIED DRUG; ZINC BILINDIONE DERIVATIVE; ZINC COMPLEX;

ALKYLATION; ARTICLE; CHIRALITY; CIRCULAR DICHROISM; ENANTIOMER; MOLECULAR MODEL; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0031736199     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980819j     Document Type: Article

References (47)

1. Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1992, 31, 1124-1134.
2. (a) Bonfiglio, J. V.; Bonnett, R.; Hursthouse, M. B.; Malik, K. M. J. Chem. Soc., Chem. Commun. 1977, 83-84.
3. (b) Balch, A. L.; Mazzanti, M.; Noll, B. C.; Olmstead, N. M. J. Am. Chem. Soc. 1994, 116, 9114.
4. Lehner, H.; Riemer, W.; Schaffner, K. Liebigs Ann. Chem. 1979, 1798.
5. (a) Lightner, D. A.; Gawronski, J. K.; Wijekoon, W. M. D. J. Am. Chem. Soc. 1987, 109, 6354.
6. (b) Krois, D. Tetrahedron 1993, 49, 8855-8864.
7. For chiral induction in biliverdin by complexation with proteins, see: (a) Huber, R.; Schneider, M.; Mayr, I.; Muller, R.; Deutzmann, R.; Suter, F.; Zuber, H.; Falk, H.; Kayser, H. J. Mol. Biol. 1987, 198, 499-513. (b) Marko, H.; Mueller, N.; Falk, H. Monatsh, Chem. 1989, 120, 163. (c) Trull, F. R.; Ibars, O.; Lightner, D. A. Arch. Biochem. Biophys. 1992, 298, 710-14. (d) Wagner, U. G.; Muller, N.; Schmitzberger, W.; Falk, H.; Kratky, C. J. Mol. Biol. 1995, 247, 326-337.
8. For chiral induction in biliverdin by complexation with proteins, see: (a) Huber, R.; Schneider, M.; Mayr, I.; Muller, R.; Deutzmann, R.; Suter, F.; Zuber, H.; Falk, H.; Kayser, H. J. Mol. Biol. 1987, 198, 499-513. (b) Marko, H.; Mueller, N.; Falk, H. Monatsh, Chem. 1989, 120, 163. (c) Trull, F. R.; Ibars, O.; Lightner, D. A. Arch. Biochem. Biophys. 1992, 298, 710-14. (d) Wagner, U. G.; Muller, N.; Schmitzberger, W.; Falk, H.; Kratky, C. J. Mol. Biol. 1995, 247, 326-337.
9. For chiral induction in biliverdin by complexation with proteins, see: (a) Huber, R.; Schneider, M.; Mayr, I.; Muller, R.; Deutzmann, R.; Suter, F.; Zuber, H.; Falk, H.; Kayser, H. J. Mol. Biol. 1987, 198, 499-513. (b) Marko, H.; Mueller, N.; Falk, H. Monatsh, Chem. 1989, 120, 163. (c) Trull, F. R.; Ibars, O.; Lightner, D. A. Arch. Biochem. Biophys. 1992, 298, 710-14. (d) Wagner, U. G.; Muller, N.; Schmitzberger, W.; Falk, H.; Kratky, C. J. Mol. Biol. 1995, 247, 326-337.
10. For chiral induction in biliverdin by complexation with proteins, see: (a) Huber, R.; Schneider, M.; Mayr, I.; Muller, R.; Deutzmann, R.; Suter, F.; Zuber, H.; Falk, H.; Kayser, H. J. Mol. Biol. 1987, 198, 499-513. (b) Marko, H.; Mueller, N.; Falk, H. Monatsh, Chem. 1989, 120, 163. (c) Trull, F. R.; Ibars, O.; Lightner, D. A. Arch. Biochem. Biophys. 1992, 298, 710-14. (d) Wagner, U. G.; Muller, N.; Schmitzberger, W.; Falk, H.; Kratky, C. J. Mol. Biol. 1995, 247, 326-337.
11. For biliverdin bearing chiral peptides via a covalent bond, see: (a) Krois, D.; Lehner, H. J. Chem. Soc., Perkin Trans. 2 1987, 219-225. (b) Krois, D.; Lehner, H. J. Chem. Soc., Perkin Trans. 2 1987, 1523-1526. (c) Krois, D.; Lehner, H. J. Chem. Soc., Perkin Trans 2 1990, 1745-1755
12. For biliverdin bearing chiral peptides via a covalent bond, see: (a) Krois, D.; Lehner, H. J. Chem. Soc., Perkin Trans. 2 1987, 219-225. (b) Krois, D.; Lehner, H. J. Chem. Soc., Perkin Trans. 2 1987, 1523-1526. (c) Krois, D.; Lehner, H. J. Chem. Soc., Perkin Trans 2 1990, 1745-1755
13. For biliverdin bearing chiral peptides via a covalent bond, see: (a) Krois, D.; Lehner, H. J. Chem. Soc., Perkin Trans. 2 1987, 219-225. (b) Krois, D.; Lehner, H. J. Chem. Soc., Perkin Trans. 2 1987, 1523-1526. (c) Krois, D.; Lehner, H. J. Chem. Soc., Perkin Trans 2 1990, 1745-1755
14. For chirally bridged biliverdins, see: (a) Krois, D.; Lehner, H. J. Chem. Soc., Perkin Trans. 2 1989, 2085-2090. (b) Krois, D.; Lehner, H. J. Chem. Soc., Perkin Trans. 1 1989, 2179-2185. (c) Krois, D.; Lehner, H. J. Chem. Soc., Perkin Trans. 2 1993, 1351-1360. (d) Krois, D.; Lehner, H. J. Chem. Soc., Perkin Trans. 2. 1993, 1837-1840.
15. For chirally bridged biliverdins, see: (a) Krois, D.; Lehner, H. J. Chem. Soc., Perkin Trans. 2 1989, 2085-2090. (b) Krois, D.; Lehner, H. J. Chem. Soc., Perkin Trans. 1 1989, 2179-2185. (c) Krois, D.; Lehner, H. J. Chem. Soc., Perkin Trans. 2 1993, 1351-1360. (d) Krois, D.; Lehner, H. J. Chem. Soc., Perkin Trans. 2. 1993, 1837-1840.
16. For chirally bridged biliverdins, see: (a) Krois, D.; Lehner, H. J. Chem. Soc., Perkin Trans. 2 1989, 2085-2090. (b) Krois, D.; Lehner, H. J. Chem. Soc., Perkin Trans. 1 1989, 2179-2185. (c) Krois, D.; Lehner, H. J. Chem. Soc., Perkin Trans. 2 1993, 1351-1360. (d) Krois, D.; Lehner, H. J. Chem. Soc., Perkin Trans. 2. 1993, 1837-1840.
17. For chirally bridged biliverdins, see: (a) Krois, D.; Lehner, H. J. Chem. Soc., Perkin Trans. 2 1989, 2085-2090. (b) Krois, D.; Lehner, H. J. Chem. Soc., Perkin Trans. 1 1989, 2179-2185. (c) Krois, D.; Lehner, H. J. Chem. Soc., Perkin Trans. 2 1993, 1351-1360. (d) Krois, D.; Lehner, H. J. Chem. Soc., Perkin Trans. 2. 1993, 1837-1840.
18. Green, M. M.; Peterson, N. C.; Sato, T.; Teramoto, A.; Cook, R.; Lifson, S. Science 1995, 268, 1860.
19. For review of supramolecular chemistry of helical molecules, see: Piguet, C.; Bernardinelli, G.; Hopfgartner, G. Chem. Rev. 1997, 97, 2005-2062.
20. Reetz, M. T.; Beuttenmüller, E. W.; Goddard, R. Tetrahedron Lett. 1997, 38, 3211-3214.
21. Yashima, E.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1997, 119, 6345-6359.
22. For preliminary account of this work, see: Mizutani, T.; Yagi, S.; Honmaru, A.; Ogoshi, H. J. Am. Chem. Soc. 1996, 118, 5318-5319.
23. (a) Shrout, D. P.; Lightner, D. A. Synthesis 1990, 1062.
24. (b) Shrout, D. P.; Puzicha, G.; Lightner, D. A. Synthesis 1992, 328.
25. (a) Fuhrhop, J.-H.; Salek, A.; Subramanian, J.; Mengersen, C.; Besecke, S. Liebigs Ann. Chem. 1975, 1131-1147.
26. (b) Fuhrhop, J.-H.; Kruger, P.; Sheldrick, W. S. Liebigs Ann. Chem. 1977, 339.
27. The oxoniaporphyrin was then cleaved to yield a 19-methoxy-1-bilinone derivative: (c) Fuhrhop, J.-H.; Kruger, P. Liebigs Ann. Chem. 1977, 360.
28. 2), phenylalanine methyl ester (Phe-OMe), tryptophan methyl ester (Trp-OMe), phenylglycine methyl ester (PhGly-OMe), and proline methyl ester (ProOMe).
29. Mizutani, T.; Erna, T.; Yoshida, T.; Kuroda, Y.; Ogoshi, H. Inorg. Chem. 1993, 32, 2072.
30. (a) Bulke, M. J.; Pratt, D. C.; Moscowitz, A. Biochemistry 1972, 11, 1, 4025-4031.
31. (b) Blauer, G.; Wagniere, G. J. Am. Chem. Soc. 1975, 97, 1949-1954.
32. (c) Wagniere, G.; Blauer, G. J. Am. Chem. Soc. 1976, 98, 7806-7810.
33. (d) Scheer, H.; Formanek, H.; Schneider, S. Photochem. Photobiol. 1982, 36, 259-272.
34. Sturrock, E. D.; Bull, J. R.; Kirsch, R. E.; Pandey, R. K.; Senge, M. O.; Smith, K. M. J. Chem. Soc., Chem. Commun. 1993, 872-874.
35. Diastereomer excess determined by signal integration and that by the binding constants agreed within 15% except for the 4-Ala-OMe, 4-18, 4-20, 8-18, and 8-20 complexes.
36. The slope of the plot for 4 was 121.8 and that for 8 was 118.5.
37. Mizutani, T.; Murakami, T.; Kurahashi, T.; Ogoshi, H. J. Org. Chem. 1996, 61, 539.
38. Unusual behavior in helicity induction by Pro-OMe is readily understood if the coordination geometry around zinc should be much different for the secondary amine.
39. (a) Gilat, G. J. Phys. A: Math, Gen. 1989, 22, L545-L550.
40. (b)Alvira, E. Amino Acids (Vienna) 1992, 2, 97-102.
41. (c) Caravella, J. A.; Richards, W. G. Eur. J. Med. Chem. 1995, 30, 727-728.
42. Riddick, J. A.; Bunger, W. B.; Sakano, T. K. Organic Solvents; Wiley and Sons: New York, 1986.
43. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, Revision D.4; Gaussian, Inc.: Pittsburgh, PA, 1996.
44. Falk, H.; Schlederer, T. Liebigs Ann. Chem. 1979, 1560-1570.
45. Falk, H.; Grubmeyer, K.; Thirring, K. Z. Naturforsh. 1978, 33b, 924-931.
46. Welch, J. T.; Seper, K. W. J. Org. Chem. 1988, 53, 2991-2999.
47. Terunuma, D.; Kato, M.; Kamei, M.; Uchida, H.; Ueno, S.; Nohira, H. Bull. Chem. Soc. Jpn. 1986, 59, 3581-3587.