Syntheses and redox behavior of novel cyclic hosts having multiple redox centers of NAD+ analogue

Tetrahedron Letters

Volumn 38, Issue 22, 1997, Pages 3939-3942

  Kuroda, Yasuhisa ^a   Seshimo, Hidenori ^b   Kondo, Toshio ^b   Shiba, Masana ^b   Ogoshi, Hisanobu ^b  

^a KYOTO INSTITUTE OF TECHNOLOGY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

cyclophane; NAD+ model; reduction potential

Indexed keywords

CYCLOPHANE DERIVATIVE; NICOTINAMIDE ADENINE DINUCLEOTIDE; NICOTINAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; OXIDATION REDUCTION POTENTIAL; SYNTHESIS;

EID: 0030914137     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00784-3     Document Type: Article

References (15)

1. Vögtle F. Cyclophane in Topics in Current Chemistry; Springer-Verlag, Berline, 1983. Vögtle, F. Supramolecular Chemistry; John Wiley & Sons, Inc.: Chichester, New York, Brisbane, Toronto, Singapore, 1991. Atwood, J. L.; Davies, J. E. D.; Macnicol, D. D. Inclusion Compounds; Oxford University Press: Oxford, New York, Tokyo, 1991; Vol. 4. Lehn, J.-M. Supramolecular Chemistry; VCH: Weinheim, New York, Basel, Cambridge, Tokyo, 1995.
2. Vögtle F. Cyclophane in Topics in Current Chemistry; Springer-Verlag, Berline, 1983. Vögtle, F. Supramolecular Chemistry; John Wiley & Sons, Inc.: Chichester, New York, Brisbane, Toronto, Singapore, 1991. Atwood, J. L.; Davies, J. E. D.; Macnicol, D. D. Inclusion Compounds; Oxford University Press: Oxford, New York, Tokyo, 1991; Vol. 4. Lehn, J.-M. Supramolecular Chemistry; VCH: Weinheim, New York, Basel, Cambridge, Tokyo, 1995.
3. Vögtle F. Cyclophane in Topics in Current Chemistry; Springer-Verlag, Berline, 1983. Vögtle, F. Supramolecular Chemistry; John Wiley & Sons, Inc.: Chichester, New York, Brisbane, Toronto, Singapore, 1991. Atwood, J. L.; Davies, J. E. D.; Macnicol, D. D. Inclusion Compounds; Oxford University Press: Oxford, New York, Tokyo, 1991; Vol. 4. Lehn, J.-M. Supramolecular Chemistry; VCH: Weinheim, New York, Basel, Cambridge, Tokyo, 1995.
4. Vögtle F. Cyclophane in Topics in Current Chemistry; Springer-Verlag, Berline, 1983. Vögtle, F. Supramolecular Chemistry; John Wiley & Sons, Inc.: Chichester, New York, Brisbane, Toronto, Singapore, 1991. Atwood, J. L.; Davies, J. E. D.; Macnicol, D. D. Inclusion Compounds; Oxford University Press: Oxford, New York, Tokyo, 1991; Vol. 4. Lehn, J.-M. Supramolecular Chemistry; VCH: Weinheim, New York, Basel, Cambridge, Tokyo, 1995.
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9. d) Kellogg, R. M. Angew. Chem. Int. Ed. Engl. 1984, 23, 782-794, and the other papers are cited therein.
10. The molecules were optimized on Spartan (Wavefunction Inc.) by using AM-1 method.
11. 35Cl] calcd 971.5413, obsd 971.5500.
12. Fukuzumi, S.; Koumitsu, S.; Hironaka, K.; Tanaka, T. J. Am. Chem. Soc. 1987, 109, 305-316. Fukuzumi, S.; Nishizawa, N.; Tanaka, T. J. Chem. Soc. Perkin Trans. II 1985, 371. Fukuzumi, S.; Hironaka, K.; Nishizawa, N.; Tanaka, T. Bull. Chem. Soc. Jpn. 1983, 56, 2220.
13. Fukuzumi, S.; Koumitsu, S.; Hironaka, K.; Tanaka, T. J. Am. Chem. Soc. 1987, 109, 305-316. Fukuzumi, S.; Nishizawa, N.; Tanaka, T. J. Chem. Soc. Perkin Trans. II 1985, 371. Fukuzumi, S.; Hironaka, K.; Nishizawa, N.; Tanaka, T. Bull. Chem. Soc. Jpn. 1983, 56, 2220.
14. Fukuzumi, S.; Koumitsu, S.; Hironaka, K.; Tanaka, T. J. Am. Chem. Soc. 1987, 109, 305-316. Fukuzumi, S.; Nishizawa, N.; Tanaka, T. J. Chem. Soc. Perkin Trans. II 1985, 371. Fukuzumi, S.; Hironaka, K.; Nishizawa, N.; Tanaka, T. Bull. Chem. Soc. Jpn. 1983, 56, 2220.
15. The weak interactions between two pyridinium moieties of 1 - 3 possibly indicate that both moieties are reduced at the same potential. In any case, the observed potentials are considered to be that of the first one electron reduction for one pyridinium moiety to give radical species (not anion radical) as the product, though the second potential can not be detected by the present method due to the irreversibility of the processes, see ref. 5.