Molecular recognition of α,ω-diamines by metalloporphyrin dimer

Tetrahedron Letters

Volumn 38, Issue 9, 1997, Pages 1603-1606

  Hayashi, Takashi ^a   Nonoguchi, Masanori ^a   Aya, Toshihiro ^a   Ogoshi, Hisanobu ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

METALLOPORPHYRIN;

ARTICLE; BINDING AFFINITY; CHEMICAL BINDING; CIRCULAR DICHROISM; COMPLEX FORMATION; MOLECULAR RECOGNITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EID: 0031550874     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00123-8     Document Type: Article

References (19)

1. 1. Ogoshi, H.; Kuroda, Y.; Mizutani, T.; Hayashi, T. Pure Appl. Chem. 1996, 68, 1411-1415.
2. 2. Mizutani, T.; Ema, T.; Yoshida, T.; Renné, T.; Ogoshi, H. Inorg. Chem. 1994, 33, 3558-3566.
3. 3. Lehn, J.-M. In Biomimetic Chemistry; Yoshida, Z.-I.; Ise, N., Eds.; Studies in Organic Chemistry 13; Kodansha: Tokyo, 1983; pp 163-187.
4. 3. Lehn, J.-M. In Biomimetic Chemistry; Yoshida, Z.-I.; Ise, N., Eds.; Studies in Organic Chemistry 13; Kodansha: Tokyo, 1983; pp 163-187.
5. 4. Crossley and his co-workers have reported the bisporphyrin as a host molecule for diamine and amino acid, in which two zinc porphyrins were linked with a rigid spacer by Tröger's base. a) Crossley, M. J.; Hambley, T. W.; Mackay, L. G.; Try, A. C.; Walton, R. J. Chem. Soc., Chem. Commun. 1995, 1077-1079.
6. b) Crossley, M. J.; Mackay, L. G.; Try, A. C. J. Chem. Soc., Chem. Commun. 1995, 1925-1927.
7. 4) nm.
8. 6. The porphyrin dimer of (R)-configuration was prepared by same procedure presented in Scheme 1. The enantiomeric mixture of the porphyrin dimer obtained from racemic 1,1′-bi-2-naphthol was resolved on chiral HPLC column and first fraction was assign to 1 derived from (S)-1,1′-bi-2-naphthol. The HPLC analysis further showed that each product prepared from (S)-or (R)-binaphthol, respectively, did not contain the alternate enantiomer: column, CHIRALCEL OD (0.46 × 25 cm); eluent, hexane/2-propanol = 25 : 1.
9. 7. Harada, N; Nakanishi, K. Circular Dichroic Spectroscopy-Exciton Coupling in Organic Stereochemistry; University Science Books: Mill Valley, CA, 1983.
10. 8. (a) Ema, T.; Nemugaki, S.; Tsuboi, S.; Utaka, M. Tetrahedron Lett. 1995, 36, 5905-5908.
11. (b) Matile, S.; Berova, I.; Nakanishi, K.; Novkova, S.; Philipova, I.; Blagoev, B. J. Am. Chem. Soc. 1995, 117, 7021-7022.
12. (c) Mihara, H.; Haruta, Y.; Sakamoto, S.; Nishino, N.; Aoyagi, H. Chem. Lett. 1996, 1-2.
13. (d) Takeuchi, M.; Chin, Y.; Imada, T.; Shinkai, S. J. Chem. Soc., Chem. Commun. 1996, 1867-1868.
14. 9. This shift could be caused by the overlap of two porphyrin rings due to the complexation of 1 and 9.
15. 10. (a) Hunter, C. A.; Meah, M. N.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5773-5780.
16. (b) Anderson, H. L.; Hunter, C. A.; Meah, M. N.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5780-5789.
17. (c) Danks, I. P.; Lane, T. G.; Sutherland, I. O.; Yap, M. Tetrahedron 1992, 48, 7679-7688.
18. -1, respectively, which are twice that for binding of monoamine to porphyrin dimer 1.
19. 2 of diamine could be free.