Interconversion between point chirality and helical chirality driven by shape-sensitive interactions

Journal of the American Chemical Society

Volumn 118, Issue 22, 1996, Pages 5318-5319

  Mizutani, Tadashi ^a   Yagi, Shigeyuki ^a   Honmaru, Atsushi ^a   Ogoshi, Hisanobu ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BILIVERDIN;

ARTICLE; CHIRALITY; CIRCULAR DICHROISM; DIASTEREOISOMER; DNA STRUCTURE; PROTEIN STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0029941303     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953932p     Document Type: Article

References (24)

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12. Bennett, A.; Siegelman, H. W. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1979; Vol. 6; pp 493-520.
13. The biliverdin framework of host 1 was prepared according to the Lightner's route: (a) Shrout, D. P.; Lightner, D. A. Synthesis 1990, 1062. (b) Shrout, D. P.; Puzicha, G.; Lightner, D. A. Synthesis 1992, 328. The biliverdin was converted to oxaporphyrin: (c) Fuhrhop, J.-H.; Salek, A.; Subramanian, J.; Mengersen, C.; Besecke, S. Liebigs Ann. Chem. 1975, 1131-1147. (d) Fuhrhop. J.-H.; Kruger. P.; Sheldrick, W. S. Liebigs Ann. Chem. 1977, 339. The oxaporphyrin was then cleaved to yield the 1-O-methylbiliverdin derivative: (e) Fuhrhop. J.-H.; Kruger, P. Liebigs Ann. Chem. 1977, 360. (f) Falk, H.; Grubmayr, K.; Thirring, K. Z. Naturforsch. 1978, 33b, 924. Zinc was inserted to the biliverdin derivative: (g) Falk, H.; Schlederer, T. Liebigs Ann. Chem. 1979, 1560.
14. The biliverdin framework of host 1 was prepared according to the Lightner's route: (a) Shrout, D. P.; Lightner, D. A. Synthesis 1990, 1062. (b) Shrout, D. P.; Puzicha, G.; Lightner, D. A. Synthesis 1992, 328. The biliverdin was converted to oxaporphyrin: (c) Fuhrhop, J.-H.; Salek, A.; Subramanian, J.; Mengersen, C.; Besecke, S. Liebigs Ann. Chem. 1975, 1131-1147. (d) Fuhrhop. J.-H.; Kruger. P.; Sheldrick, W. S. Liebigs Ann. Chem. 1977, 339. The oxaporphyrin was then cleaved to yield the 1-O-methylbiliverdin derivative: (e) Fuhrhop. J.-H.; Kruger, P. Liebigs Ann. Chem. 1977, 360. (f) Falk, H.; Grubmayr, K.; Thirring, K. Z. Naturforsch. 1978, 33b, 924. Zinc was inserted to the biliverdin derivative: (g) Falk, H.; Schlederer, T. Liebigs Ann. Chem. 1979, 1560.
15. The biliverdin framework of host 1 was prepared according to the Lightner's route: (a) Shrout, D. P.; Lightner, D. A. Synthesis 1990, 1062. (b) Shrout, D. P.; Puzicha, G.; Lightner, D. A. Synthesis 1992, 328. The biliverdin was converted to oxaporphyrin: (c) Fuhrhop, J.-H.; Salek, A.; Subramanian, J.; Mengersen, C.; Besecke, S. Liebigs Ann. Chem. 1975, 1131-1147. (d) Fuhrhop. J.-H.; Kruger. P.; Sheldrick, W. S. Liebigs Ann. Chem. 1977, 339. The oxaporphyrin was then cleaved to yield the 1-O-methylbiliverdin derivative: (e) Fuhrhop. J.-H.; Kruger, P. Liebigs Ann. Chem. 1977, 360. (f) Falk, H.; Grubmayr, K.; Thirring, K. Z. Naturforsch. 1978, 33b, 924. Zinc was inserted to the biliverdin derivative: (g) Falk, H.; Schlederer, T. Liebigs Ann. Chem. 1979, 1560.
16. The biliverdin framework of host 1 was prepared according to the Lightner's route: (a) Shrout, D. P.; Lightner, D. A. Synthesis 1990, 1062. (b) Shrout, D. P.; Puzicha, G.; Lightner, D. A. Synthesis 1992, 328. The biliverdin was converted to oxaporphyrin: (c) Fuhrhop, J.-H.; Salek, A.; Subramanian, J.; Mengersen, C.; Besecke, S. Liebigs Ann. Chem. 1975, 1131-1147. (d) Fuhrhop. J.-H.; Kruger. P.; Sheldrick, W. S. Liebigs Ann. Chem. 1977, 339. The oxaporphyrin was then cleaved to yield the 1-O-methylbiliverdin derivative: (e) Fuhrhop. J.-H.; Kruger, P. Liebigs Ann. Chem. 1977, 360. (f) Falk, H.; Grubmayr, K.; Thirring, K. Z. Naturforsch. 1978, 33b, 924. Zinc was inserted to the biliverdin derivative: (g) Falk, H.; Schlederer, T. Liebigs Ann. Chem. 1979, 1560.
17. The biliverdin framework of host 1 was prepared according to the Lightner's route: (a) Shrout, D. P.; Lightner, D. A. Synthesis 1990, 1062. (b) Shrout, D. P.; Puzicha, G.; Lightner, D. A. Synthesis 1992, 328. The biliverdin was converted to oxaporphyrin: (c) Fuhrhop, J.-H.; Salek, A.; Subramanian, J.; Mengersen, C.; Besecke, S. Liebigs Ann. Chem. 1975, 1131-1147. (d) Fuhrhop. J.-H.; Kruger. P.; Sheldrick, W. S. Liebigs Ann. Chem. 1977, 339. The oxaporphyrin was then cleaved to yield the 1-O-methylbiliverdin derivative: (e) Fuhrhop. J.-H.; Kruger, P. Liebigs Ann. Chem. 1977, 360. (f) Falk, H.; Grubmayr, K.; Thirring, K. Z. Naturforsch. 1978, 33b, 924. Zinc was inserted to the biliverdin derivative: (g) Falk, H.; Schlederer, T. Liebigs Ann. Chem. 1979, 1560.
18. The biliverdin framework of host 1 was prepared according to the Lightner's route: (a) Shrout, D. P.; Lightner, D. A. Synthesis 1990, 1062. (b) Shrout, D. P.; Puzicha, G.; Lightner, D. A. Synthesis 1992, 328. The biliverdin was converted to oxaporphyrin: (c) Fuhrhop, J.-H.; Salek, A.; Subramanian, J.; Mengersen, C.; Besecke, S. Liebigs Ann. Chem. 1975, 1131-1147. (d) Fuhrhop. J.-H.; Kruger. P.; Sheldrick, W. S. Liebigs Ann. Chem. 1977, 339. The oxaporphyrin was then cleaved to yield the 1-O-methylbiliverdin derivative: (e) Fuhrhop. J.-H.; Kruger, P. Liebigs Ann. Chem. 1977, 360. (f) Falk, H.; Grubmayr, K.; Thirring, K. Z. Naturforsch. 1978, 33b, 924. Zinc was inserted to the biliverdin derivative: (g) Falk, H.; Schlederer, T. Liebigs Ann. Chem. 1979, 1560.
19. The biliverdin framework of host 1 was prepared according to the Lightner's route: (a) Shrout, D. P.; Lightner, D. A. Synthesis 1990, 1062. (b) Shrout, D. P.; Puzicha, G.; Lightner, D. A. Synthesis 1992, 328. The biliverdin was converted to oxaporphyrin: (c) Fuhrhop, J.-H.; Salek, A.; Subramanian, J.; Mengersen, C.; Besecke, S. Liebigs Ann. Chem. 1975, 1131-1147. (d) Fuhrhop. J.-H.; Kruger. P.; Sheldrick, W. S. Liebigs Ann. Chem. 1977, 339. The oxaporphyrin was then cleaved to yield the 1-O-methylbiliverdin derivative: (e) Fuhrhop. J.-H.; Kruger, P. Liebigs Ann. Chem. 1977, 360. (f) Falk, H.; Grubmayr, K.; Thirring, K. Z. Naturforsch. 1978, 33b, 924. Zinc was inserted to the biliverdin derivative: (g) Falk, H.; Schlederer, T. Liebigs Ann. Chem. 1979, 1560.
20. The chemical shift at 3.00 ppm is the average of the 46% complexed and 54% uncomplexed guest.
21. (a) Bulke, M. J.; Pratt, D. C.; Moscowitz, A. Biochemistry 1972, 11, 4025-4031.
22. (b) Blauer, G.; Wagniere, G. J. Am. Chem. Soc. 1975, 97, 1949-1954.
23. (c) Wagniere, G.; Blauer, G. J. Am. Chem. Soc. 1976, 98, 7806-7810.
24. (d) Scheer, H.; Formanek, H.; Schneider, S. Photochem. Photobiol. 1982, 36, 259-272.