Synthesis and reactivities of a novel flavoenzyme model, 5-deazaflavin with C2-symmetry

Tetrahedron Asymmetry

Volumn 8, Issue 14, 1997, Pages 2319-2323

  Yanada, Reiko ^a   Yoneda, Yoshiyuki ^a   Yazaki, Mikako ^a   Mimura, Norio ^a   Taga, Tooru ^a   Yoneda, Fumio ^a,c   Yanada, Kazuo ^b  

^a KYOTO UNIVERSITY   (Japan)

^b SETSUNAN UNIVERSITY   (Japan)

^c Fujimoto Pharmaceutical Corporation   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

5 DEAZAFLAVINE DERIVATIVE; APOPROTEIN; FLAVOPROTEIN; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE;

ARTICLE; ENERGY; ENZYME ACTIVE SITE; ENZYME STRUCTURE; ENZYME SYNTHESIS; NUCLEAR OVERHAUSER EFFECT; OXIDATION REDUCTION REACTION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0030750444     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00269-3     Document Type: Article

References (13)

1. L. D. Eirich, G. D. Vogels, and R. S. Wolfe, Biochemistry, 1978, 17, 4583; R. P. Hausinger, W. H. Orme-Johnson, and C. Walsh, Biochemistry, 1985, 24, 1629; F. Yoneda and K. Tanaka, Med. Res. Rev., 1987, 7, 477.
2. L. D. Eirich, G. D. Vogels, and R. S. Wolfe, Biochemistry, 1978, 17, 4583; R. P. Hausinger, W. H. Orme-Johnson, and C. Walsh, Biochemistry, 1985, 24, 1629; F. Yoneda and K. Tanaka, Med. Res. Rev., 1987, 7, 477.
3. L. D. Eirich, G. D. Vogels, and R. S. Wolfe, Biochemistry, 1978, 17, 4583; R. P. Hausinger, W. H. Orme-Johnson, and C. Walsh, Biochemistry, 1985, 24, 1629; F. Yoneda and K. Tanaka, Med. Res. Rev., 1987, 7, 477.
4. R. Yanada, M. Higashikawa, Y. Miwa, T. Taga, and F. Yoneda, Tetrahedron: Asymmetry, 1992, 3, 1387, and references cited therein.
5. M. Iwata, T. C. Bruice, H. L. Carrell, and J. P. Glusker, J. Am. Chem. Soc., 1980, 102, 5036.
6. F. Yoneda, Y. Sakuma, S. Mizumoto, and R. Itoh, J. Chem. Soc., Perkin Trans, 1, 1976, 1805.
7. All ab initio calculations were performed using the program GAUSSIAN 92 on a CRAY Y-MP2E/264 at the Supercomputer Laboratory, Institute for Chemical Research, Kyoto University. GAUSSIAN 92, Revision C: Frisch, M. J.; Trucks, G. W.; Head-Gordon, M.; Gill, P. M. W.; Wong, M. W.; Forseman, J. B.; Johnson, B. G.; Schlegel, H. B.; Robb, M. A.; Replogle, E. S.; Gomperts, R.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzalez, C.; Martin, R. L.; Fox, D. J.; Defress, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. A.; Gaussian Inc., Pittsburgh, PA, 1992.
8. A. Ohno, M. Ikeguchi, T. Kimura, and S. Oka, J. Am. Chem. Soc., 1979, 101, 7063.
9. 6
10. T. Kawamoto, M. Tomishima, F. Yoneda, and J. Hayami, Tetrahedron Lett., 1992, 33, 3173.
11. E. F. Pai and G. E. Schulz, J. Biol. Chem., 1983, 258, 1752.
12. 2-symmetry bis(5-deazaflavin) model. H. A. Staab, P. Kirsch, M. F. Zipplies, A. Weinges, and C. Krieger, Chem. Ber., 1994, 127, 1653.
13. F. Yoneda, Y. Sakuma, M. Ichiba, and K. Shinomura, J. Am. Chem. Soc., 1976, 98, 830.