Skip to main content
Log in

Absolute Configuration and the Structure of Chlorophyll

  • Letter
  • Published:

From Nature

View current issue Submit your manuscript

Abstract

THE structure of chlorophyll is known in considerable detail. The correct gross structure was put forward by Hans Fischer1 and confirmed in a beautiful synthesis by R. B. Woodward2,3; the relative configuration of the methyl and propionic ester groups on ring D was shown to be trans by Ficken, Johns and Linstead4; the stereochemistry and absolute configuration of the phytyl group was shown by Burrell, Jackman and Weedon5,6 to be 2′-trans-7′R,11′R and the relative configuration at C10 was shown very recently by Wolf, Brockmann, Biere and Inhoffen7,8 to be that in which the methoxycarbonyl group is trans to the propionic ester side chain on C7. (A recent review9 mentions the first X-ray crystallographic structure determination of a chlorophyll derivative, phyllochlorin ester. Success has come late in this field, because of disordered structures in the crystals of chlorophyll derivatives. The review gives no information about the absolute configuration.) The absolute configuration at C7 and C8, however, was not-known and there were therefore two diastereoisomeric structures still possible for chlorophyll. This report provides the missing information and completes the structure of chlorophyll-a (and therefore of chlorophyll-b the configuration of which has been shown10 to be the same as that of chlorophyll-a).

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Fischer, H., and Wenderoth, H., Annalen, 545, 140 (1940).

    Article  CAS  Google Scholar 

  2. Woodward, R. B., Ayer, W. A., Beaton, J. M., Bickelhaupt, F., Bonnett, R., Buchschacher, P., Closs, G. L., Dutler, H., Hannah, J., Hauck, F. P., Ito, S., Langeman, A., Le Goff, E., Leimgruber, W., Lwowski, W., Sauer, J., Valenta, Z., and Volz, H., J. Amer. Chem. Soc., 82, 3800 (1960).

    Article  CAS  Google Scholar 

  3. Woodward, R. B., Pure and Appl. Chem., 2, 383 (1961).

    Article  CAS  Google Scholar 

  4. Ficken, G. E., Johns, R. B., and Linstead, R. P., J. Chem. Soc., 2272 (1956).

  5. Burrell, J. W. K., Jackman, L. M., and Weedon, B. C. L., Proc. Chem. Soc., 263 (1959).

  6. Crabbe, P., Djerassi, C., Eisenbraun, E. J., and Liu, S., Proc. Chem. Soc., 264 (1959).

  7. Wolf, H., Brockmann, H., Biere, H., and Inhoffen, H. H., Annalen, 704, 208 (1967).

    Article  CAS  Google Scholar 

  8. Closs, G. L., Katz, J. J., Pennington, F. C., Thomas, M. R., and Strain, H. H., J. Amer. Chem. Soc., 85, 3809 (1963).

    Article  CAS  Google Scholar 

  9. Hoppe, W., Angew. Intern. Ed. (in English), 5, 267 (1966).

    Article  Google Scholar 

  10. Fischer, H., and Gibian, H., Annalen, 552, 153 (1942).

    Article  CAS  Google Scholar 

  11. Ficken, G. E., Johns, R. B., and Linstead, R. P., J. Chem. Soc., 2280 (1956).

  12. Ault, A., J. Chem. Ed., 42, 269 (1965) based on Theilacker, W., and Winkler, H.-G., Chem. Ber., 87, 690 (1954).

    Article  CAS  Google Scholar 

  13. Asher, J. D. M., and Sim, G. A., J. Chem. Soc., 1584 and 6041 (1965).

  14. McPhail, A. T., Rimmer, B., Robertson, J. Monteath, and Sim, G. A., J. Chem. Soc., B, 101 (1967).

  15. Nakazaki, M., and Arakawa, H., Proc. Chem. Soc., 151 (1962).

  16. Nakazaki, M., and Arakawa, H., Bull. Chem. Soc. Japan, 37, 464 (1964).

    Google Scholar 

  17. Nakazaki, M., Bull. Chem. Soc. Japan, 35, 1904 (1962).

    Google Scholar 

  18. Nakazaki, M., and Ikematsu, K., Bull. Chem. Soc. Japan, 37, 459 (1964).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

FLEMING, I. Absolute Configuration and the Structure of Chlorophyll. Nature 216, 151–152 (1967). https://doi.org/10.1038/216151a0

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1038/216151a0

  • Springer Nature Limited

This article is cited by

Navigation