University Chemical Laboratory, University of Cambridge
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).
- Fischer, H. , and Wenderoth, H. , Annalen, 545, 140 (1940). | ChemPort |
- 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 | ISI | ChemPort |
- Woodward, R. B. , Pure and Appl. Chem., 2, 383 (1961). | ChemPort |
- Ficken, G. E. , Johns, R. B. , and Linstead, R. P. , J. Chem. Soc., 2272 (1956).
- Burrell, J. W. K. , Jackman, L. M. , and Weedon, B. C. L. , Proc. Chem. Soc., 263 (1959).
- Crabbe, P. , Djerassi, C. , Eisenbraun, E. J. , and Liu, S. , Proc. Chem. Soc., 264 (1959).
- Wolf, H. , Brockmann, H. , Biere, H. , and Inhoffen, H. H. , Annalen, 704, 208 (1967). | ISI | ChemPort |
- Closs, G. L. , Katz, J. J. , Pennington, F. C. , Thomas, M. R. , and Strain, H. H. , J. Amer. Chem. Soc., 85, 3809 (1963). | Article | ISI | ChemPort |
- Hoppe, W. , Angew. Intern. Ed. (in English), 5, 267 (1966). | ISI |
- Fischer, H. , and Gibian, H. , Annalen, 552, 153 (1942). | ChemPort |
- Ficken, G. E. , Johns, R. B. , and Linstead, R. P. , J. Chem. Soc., 2280 (1956).
- Ault, A. , J. Chem. Ed., 42, 269 (1965) based on Theilacker, W. , and Winkler, H.-G. , Chem. Ber., 87, 690 (1954). | ISI | ChemPort |
- Asher, J. D. M. , and Sim, G. A. , J. Chem. Soc., 1584 and 6041 (1965).
- McPhail, A. T. , Rimmer, B. , Robertson, J. Monteath , and Sim, G. A. , J. Chem. Soc., B, 101 (1967).
- Nakazaki, M. , and Arakawa, H. , Proc. Chem. Soc., 151 (1962).
- Nakazaki, M. , and Arakawa, H. , Bull. Chem. Soc. Japan, 37, 464 (1964).
- Nakazaki, M. , Bull. Chem. Soc. Japan, 35, 1904 (1962).
- Nakazaki, M. , and Ikematsu, K. , Bull. Chem. Soc. Japan, 37, 459 (1964). | ISI | ChemPort |