X-ray structures of two oxidation states of a flavin-nicotinamide biscoenzyme and models for flavin—nicotinamide interactions

Abstract

The flavin nicotinamide biscoenzymes FlOX–C3–Nic+ and H2Flred–C3–Nic+ assume extended conformations in the solid state. In both derivatives the nicotinamide and flavin groups associate through hydrogen bonding. The bending angle of the reduced flavin moiety is less than half that in any previously reported 1,5-dihydroflavin structure. This effect is apparently due to ring stacking interactions.

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References

  1. 1

    Massey, V. & Ghisla, S. Ann. N. Y. Acad. Sci. 227, 446–465 (1974).

    ADS  Article  Google Scholar 

  2. 2

    Proffitt, R. T., Ingraham, L. L. & Blankenhorn, G. Biochem. biophys. Acta. 362, 534–548 (1974).

    CAS  Article  Google Scholar 

  3. 3

    Sakurai, T. & Hosoya, H. Biochem. biophys. Acta 112, 459–468 (1966).

    CAS  Google Scholar 

  4. 4

    Porter, D. J. T., Blankenhorn, G. & Ingraham, L. L. Biochem. biophys. Res. Commun. 52, 447–452 (1973).

    CAS  Article  Google Scholar 

  5. 5

    Blankenhorn, G. Eur. J. Biochem. 50, 351–356 (1975); 67, 67–80 (1976): Biochemistry 14, 3172–3176 (1975); Flavins and Flavoproteins. Vol. V (ed. Singer. T. P.), 261–267 (Elsevier, Amsterdam, 1976).

    Google Scholar 

  6. 6

    Bruice, T. C., Main, L., Smith, S. & Bruice, P. Y. J. Am. chem. Soc. 93, 7325–7328 (1971).

    Article  Google Scholar 

  7. 7

    Gumbley, S. J. & Main, L. Tetrahedron Lett. 3209–3212 (1976).

  8. 8

    Steffens, J. J. & Chipman, D. M. J. Am. chem. Soc. 93, 6694–6696 (1971).

    CAS  Article  Google Scholar 

  9. 9

    Bruice, T. C. Prog. bioorg. Chem. 4, 1–87 (1976).

    CAS  Google Scholar 

  10. 10

    Brüstlein, M. & Bruice, T. C. J. Am. chem. Soc. 94, 6548–6549 (1972).

    Article  Google Scholar 

  11. 11

    Fisher, J. & Walsh, C. J. Am. chem. Soc. 96, 4345–4346 (1974).

    CAS  Article  Google Scholar 

  12. 12

    Porter, D. J. T. & Voet, D. submitted to Acta crystallogr.

  13. 13

    Main, P., Woolfson, M. M. & Germain, G. MULTAN. A Computer Program for the Automatic Solution of Crystal Structures (Department of Physics, University of York. York. UK, 1971).

    Google Scholar 

  14. 14

    Voet, D. & Rich, A. Prog. Nucl. Acid Res. molec. Biol. 10, 183–265 (1970).

    CAS  Article  Google Scholar 

  15. 15

    Wang, M. & Fritchie, C. J. Acta crystallogr. B 29, 2040–2045 (1973).

    CAS  Article  Google Scholar 

  16. 16

    Voet, D. J. Am. chem. Soc. 95, 3763–3770 (1973).

    CAS  Article  Google Scholar 

  17. 17

    Johnson, P. L., Maier, C. A. & Paul, I. C. J. Am. chem. Soc. 95, 5370–5377 (1973).

    CAS  Article  Google Scholar 

  18. 18

    Freeman, G. R. & Bugg, C. E. Acta crystallogr. B 30, 431–443 (1974).

    CAS  Article  Google Scholar 

  19. 19

    Herriott, J. R., Cammerman, A. & Deranleau, D. R. J. Am. chem. Soc. 96, 1585–1589 (1974).

    CAS  Article  Google Scholar 

  20. 20

    Singh, C. Acta crystallogr. 19, 861–864 (1965).

    CAS  Article  Google Scholar 

  21. 21

    Kierkegaard, P. et al. Flavins and Flavoproteins, Vol. III (ed. Kamen. H.) 1–22 (University Park. Baltimore, 1971).

    Google Scholar 

  22. 22

    Wright, W. B. & King, G. S. D. Acta crystallogr. 7, 283–288 (1954).

    CAS  Article  Google Scholar 

  23. 23

    Dudley, K. H., Ehrenberg, A., Hemmerich, P. & Müller, F. Helv. Chim. Acta 47, 1354–1383 (1964).

    CAS  Article  Google Scholar 

  24. 24

    Leijonmarch, M. & Werner, P.-E. Acta chem. scand. 25, 2273–2290 (1971).

    Article  Google Scholar 

  25. 25

    Wang, M. & Fritchie, C. L. Jr, Acta crystallogr. B 29, 2040–2045 (1973).

    CAS  Article  Google Scholar 

  26. 26

    Porter, D. J. T., Voet, J. G. & Bright, H. J. J. biol. Chem. 248, 4400–4416 (1973).

    CAS  PubMed  Google Scholar 

  27. 27

    Anderson, B. M. & Kaplan, N. O. J. biol. Chem. 234, 1226–1232 (1959).

    CAS  PubMed  Google Scholar 

  28. 28

    vonGlehn, M. & Norrestam, R. Acta chem. scand. 26, 1490–1492 (1972).

    CAS  Article  Google Scholar 

  29. 29

    Tauscher, L., Ghisla, S. & Hemmerich, P. Helv. chim. Acta 56, 630–644 (1973).

    CAS  Article  Google Scholar 

  30. 30

    Burnett, R. M. et al. J. biol. Chem. 249, 4383–4392 (1974).

    CAS  PubMed  PubMed Central  Google Scholar 

  31. 31

    Ludwig, M. L. et al. in Flavins and Flavoproteins Vol. V. (ed. Singer, T. P.) 393–404 (Elsevier, Amsterdam, 1976).

    Google Scholar 

  32. 32

    Anderson, R. D. et al. Proc. natn. Acad Sci. U.S. A. 69, 3189–3191 (1972).

    ADS  Article  Google Scholar 

  33. 33

    James, T. L., Ludwig, M. L. & Cohn, M. Proc. natn. Acad. Sci. U.S.A. 70, 3293–3295 (1973).

    ADS  Article  Google Scholar 

  34. 34

    Ludwig, M. L. et al. Cold Spring Harb. Symp. quant. Biol. 36, 369–380 (1971).

    CAS  Article  Google Scholar 

  35. 35

    Scarbrough, F. E., Shieh, H.-S. & Voet, D. Proc. natn. Acad. Sci. U.S.A. 73, 3807–3811 (1976); Acta crystallogr. B 33, (in the press).

    ADS  CAS  Article  Google Scholar 

  36. 36

    Ghisla, S., Massey, V., Lhoste, J. M. & Mayhew, S. G. Biochemistry 13, 589–597 (1974).

    CAS  Article  Google Scholar 

  37. 37

    Slifkin, M. A. Physico-Chemical Properties of Nucleic Acids 1, (ed. Duchesne, J.), 67–98 (Academic. New York, 1973).

    Google Scholar 

  38. 38

    Ts'o, P. O. P. Fine Structure of Proteins and Nucleic Acids (eds Fasman, G. D. & Timasheff, S. N.) 49–190 (Marcel Dekker, New York, 1970).

    Google Scholar 

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Porter, D., Bright, H. & Voet, D. X-ray structures of two oxidation states of a flavin-nicotinamide biscoenzyme and models for flavin—nicotinamide interactions. Nature 269, 213–217 (1977). https://doi.org/10.1038/269213a0

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