Skip to main content

Thank you for visiting nature.com. You are using a browser version with limited support for CSS. To obtain the best experience, we recommend you use a more up to date browser (or turn off compatibility mode in Internet Explorer). In the meantime, to ensure continued support, we are displaying the site without styles and JavaScript.

  • Article
  • Published:

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

Nature volume 269, pages 213–217 (1977)Cite this article

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.

This is a preview of subscription content, access via your institution

Access options

Buy this article

  • Purchase on Springer Link
  • Instant access to full article PDF
Buy now

Prices may be subject to local taxes which are calculated during checkout

Similar content being viewed by others

References

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

    Article  ADS  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

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

    CAS  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

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

    Article  Google Scholar 

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

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

    Article  CAS  PubMed  Google Scholar 

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

    CAS  Google Scholar 

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

    Article  PubMed  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

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

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    CAS  PubMed  Google Scholar 

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

    CAS  PubMed  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

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

    CAS  PubMed  Google Scholar 

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

    Google Scholar 

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

    Article  ADS  Google Scholar 

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

    Article  ADS  Google Scholar 

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

    Article  CAS  Google Scholar 

  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).

    Article  ADS  CAS  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

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

    Google Scholar 

  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 

Download references

Author information

Author notes

  1. David J. T. Porter

    Present address: Novo Laboratories, 59 Danbury Road, Wilton, Connecticut

Authors and Affiliations

  1. Department of Biochemistry and Biophysics, University of Pennsylvania, Philadelphia, Pennsylvania, 19104

    David J. T. Porter & Harold J. Bright

  2. Department of Chemistry and Laboratory for Research on the Structure of Matter, University of Pennsylvania, Philadelphia, Pennsylvania, 19104

    Donald Voet

Authors
  1. David J. T. Porter
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Harold J. Bright
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Donald Voet
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

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

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1038/269213a0

Comments

By submitting a comment you agree to abide by our Terms and Community Guidelines. If you find something abusive or that does not comply with our terms or guidelines please flag it as inappropriate.

Search

Advanced search

Quick links

Nature Briefing

Sign up for the Nature Briefing newsletter — what matters in science, free to your inbox daily.

Get the most important science stories of the day, free in your inbox. Sign up for Nature Briefing