메뉴 건너뛰기




Volumn 119, Issue 31, 1997, Pages 7281-7290

Molecular recognition of ubiquinone analogues. Specific interaction between quinone and functional porphyrin via multiple hydrogen bonds

Author keywords

[No Author keywords available]

Indexed keywords

PORPHYRIN DERIVATIVE; UBIQUINONE DERIVATIVE;

EID: 0030749450     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9711526     Document Type: Article
Times cited : (73)

References (75)
  • 2
    • 0000873192 scopus 로고
    • Beezer, A. E., Ed.; Academic Press: New York
    • (b) Eftink, M.; Biltonen, R. In Biological Microcalorimetry; Beezer, A. E., Ed.; Academic Press: New York, 1980; pp 343-412.
    • (1980) Biological Microcalorimetry , pp. 343-412
    • Eftink, M.1    Biltonen, R.2
  • 4
    • 0000979957 scopus 로고
    • Molecular Recognition (Tetrahedron Symposia No. 56)
    • For recent reviews: Hamilton, A. D., Ed.; Molecular Recognition (Tetrahedron Symposia No. 56). Tetrahedron 1995, 51.
    • (1995) Tetrahedron , pp. 51
    • Hamilton, A.D.1
  • 6
    • 0001202627 scopus 로고    scopus 로고
    • For example: (a) Ogoshi, H.; Kuroda, Y.; Mizutani, T.; Hayashi, T. Pure Appl. Chem. 1996, 68, 1411. (b) Ogoshi, H.; Mizutani, T. In Comprehensive Supramolecular Chemistry; Murakami, Y., Ed.; Oxford, 1996; Vol. 4; p 337.
    • (1996) Pure Appl. Chem. , vol.68 , pp. 1411
    • Ogoshi, H.1    Kuroda, Y.2    Mizutani, T.3    Hayashi, T.4
  • 7
    • 0001202627 scopus 로고    scopus 로고
    • Murakami, Y., Ed.; Oxford
    • For example: (a) Ogoshi, H.; Kuroda, Y.; Mizutani, T.; Hayashi, T. Pure Appl. Chem. 1996, 68, 1411. (b) Ogoshi, H.; Mizutani, T. In Comprehensive Supramolecular Chemistry; Murakami, Y., Ed.; Oxford, 1996; Vol. 4; p 337.
    • (1996) Comprehensive Supramolecular Chemistry , vol.4 , pp. 337
    • Ogoshi H1    Mizutani T2
  • 8
    • 0004165558 scopus 로고
    • Springer-Verlag: New York
    • Gennis, R. B. Biomembranes; Springer-Verlag: New York, 1989.
    • (1989) Biomembranes
    • Gennis, R.B.1
  • 12
    • 0040891425 scopus 로고
    • For recent reviews on ET reactions by covalently or noncovalently linked porphyrin-quinone compounds: (a) Wasielewski, M. R. Chem. Rev. 1992, 92, 435.
    • (1992) Chem. Rev. , vol.92 , pp. 435
    • Wasielewski, M.R.1
  • 40
    • 1842329892 scopus 로고    scopus 로고
    • note
    • 9a The binding constant determined from the NMR titrimetric measurement is exactly consistent with that from the UV-vis titrimetric one.
  • 41
    • 1842338244 scopus 로고
    • The detected planarity of porphyrin ring suggests that the remarkable structural changes upon complexation between 1 and 4f does not occur. Thus, the structure of 1 seems to be preorganized for ubiquinone analogues. The planarity of the porphyrin ring in tetraphenylporphyrin has been reported previously. For example: (a) Hamor, M. J.; Hamor, T. A.; Hoard, J. L. J. Am. Chem. Soc. 1964, 86, 1983. (b) Senge, M. O.; Forsyth, T. P.; Nguyen, L. T.; Smith, K. M. Angew. Chem. Int. Ed. Engl. 1994, 33, 2485.
    • (1964) J. Am. Chem. Soc. , vol.86 , pp. 1983
    • Hamor, M.J.1    Hamor, T.A.2    Hoard, J.L.3
  • 42
    • 33751129650 scopus 로고
    • The detected planarity of porphyrin ring suggests that the remarkable structural changes upon complexation between 1 and 4f does not occur. Thus, the structure of 1 seems to be preorganized for ubiquinone analogues. The planarity of the porphyrin ring in tetraphenylporphyrin has been reported previously. For example: (a) Hamor, M. J.; Hamor, T. A.; Hoard, J. L. J. Am. Chem. Soc. 1964, 86, 1983. (b) Senge, M. O.; Forsyth, T. P.; Nguyen, L. T.; Smith, K. M. Angew. Chem. Int. Ed. Engl. 1994, 33, 2485.
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 2485
    • Senge, M.O.1    Forsyth, T.P.2    Nguyen, L.T.3    Smith, K.M.4
  • 43
    • 1842292340 scopus 로고    scopus 로고
    • note
    • Torsion angles about MeO groups are as follows: C(100)-O(12)-C(96)-C(91) = 175.5°, C(99)-O(11)-C(95)-C(96) = 111.7°, C(98)-O(9)-C(93)-C(94) = 166.9°, C(97)-O(8)-C(92)-C(93) = 121.4°, C(104)-O(13)-C(101)-C(102) = 77.8°, and C(105)-O(15)-C(103)-C(101) = -0.9°.
  • 44
    • 1842330457 scopus 로고    scopus 로고
    • note
    • 1·4a
  • 45
    • 1842410878 scopus 로고    scopus 로고
    • note
    • 1·4b-1·4a = ΔH°1·4b - ΔH°1·4a.
  • 69
    • 1842416150 scopus 로고    scopus 로고
    • note
    • β carbons of the four pyrrole rings were not detected due to the broadening derived from N-H tautomerism.
  • 70
    • 1842331059 scopus 로고    scopus 로고
    • note
    • α carbons of the four pyrrole rings were not detected due to the broadening derived from N-H tautomerism.
  • 74
    • 1842408546 scopus 로고    scopus 로고
    • SDP-Mo1EN: An Interactive Structure Solution Procedure; Enraf-Nonius: Delft, The Netherlands, 1990
    • SDP-Mo1EN: An Interactive Structure Solution Procedure; Enraf-Nonius: Delft, The Netherlands, 1990.
  • 75
    • 1842412648 scopus 로고    scopus 로고
    • teXsan: Crystal Structure Analysis Package, Molecular Structure Corp., 1985, 1992
    • teXsan: Crystal Structure Analysis Package, Molecular Structure Corp., 1985, 1992.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.