Abstract
The molecule crystallizes in spacegroup P21 with two molecules per unit cell. The unit cell dimensions area = 6.044 Å,b = 13.607 Å,c = 5.311 Å,γ = 97.55°. The density was calculated to be 1.512 g.ml.−1 and found to be 1.51 g.ml.−1 The major atoms were located by the reliable image method and the hydrogen atoms were located from a difference electron density map. Full-matrix least squares refinement of the parameters yielded an unweighted residual indexR of 0.088.
The bond lengths and angles of the amino acid grouping are consistent with values in other amino acids. The structural parameters of the aromatic system are very similar to those of noradrenaline and dopamine hydrochlorides. The crystal structure is dominated by a three-dimensional intermolecular hydrogen bonding system. The molecular conformation is different from that displayed by any other aromatic amino acid or peptide whose crystal structure is known.
Similar content being viewed by others
References
Becker, J. W. Thathachari, Y. T. and Simpson, P. G.Biochem. Biophys. Res. Comm., 1970,41, 444.
Bergin, R. ..S-104 01, Dept. of Medical Physics, Karolinska Instt., Sweden, P. 21.
Mostad, A., Ottesen, T. and Romming, C.Acta Chem. Scand., 1970,24, 1864.
Brown, S. H. and Simpson, P. G.Acta Cryst., 1970, (In press).
Buerger, M. J...J. Appl. Phys.,17, 1946, 579.
—..Vector Space, John Wiley and Sons, New York, 1959.
Busing, W. R., Martin, K. O. and Levy, H. A.ORFLS, A FORTRAN Crystallographic Least-Squares Program, ORNL-TM-305, Oak Ridge National Laboratory, Tennessee, 1962.;
—..ORFFE, A FORTRAN Crystallcgraphic Function and Error Program, ORNL-TM-306, Oak Ridge National Laboratory Tennessee, 1964.
Carlström, D. and Bergin, R.Acta Cryst., 1967,23, 313.
Djerassi, C, Brown, S. H. and Simpson, P. G.J. Am. Chem. Soc, 1968,90, 2445.
Edsall, J. T., Flory, P. J., Kendrew, J. C., Liquori, A. M., Nemethy, G., Ramachandran, G. N. and Scheraga, H. A.J. Biol. Chem., 1966,241, 1004.
Evans, W. C. and Raper, H. S.Biochem. J., 1937,31, 2162.
Gurskaya, G. V...The Molecular Structure of Amino Acids, Consultants Bureau, New York, 1958,
Sober, H. A...Handbook of Biochemistry, The Chemical Rubber Company, Cleveland, Ohio, 1968.
International Tables for X-ray Crystallography, The Kynoch Press, Birmingham, England, 1962.
Jandacek, R. J., and Earle, K.Acta Cryst., 1971,27, 841.
Johnson, C. K... ORTEP, A FORTRAN Thermal Ellipsoid Plot Program for Crystal Structure Illustrations, ORNL-3794, Oak Ridge National Laboratory, Tennessee, 1965.
Kahrl, J. H., Becker, J. W., Sholkovitz, E. R., Hopkins, T. E. and Simpson, P. G. 1970, In Preparation.
- and Simpson, P. G. .. 1970, In Preparation.
Lakshminarayan, A. V., Sasisekharan, V., and Ramachandran, G. N. InConformation of Biopolymers, Vol. I, ed. by G. N. Ramachandran, Academic Press, New York, 1967, p. 61,
Mallikarjunan, M., Rao, S. Thyagaraja, Venkatesan, K. and Sarma, V. RaghupathyActa Cryst,. 1969,25 B, 220.
Marsh, R. E. and Donohue, J.Advan. Protein Chem., 1967,22, 235.
— and Glusker, J. P...Acta Cryst, 1961,14, 1110.
Pauling, L...Nature of the Chemical Bond, Cornell University Press, Ithaca, New York, 1939.
Sedgewick, E. M...New Scientist, 1969,44, 234.
Simpson, P. G. and Becker, J. W. American Crystallographic Association, Winter Meeting, March 1970, Paper B3.
—.. 1970b, In preparation. Sly, W. G. and Shoemaker, D. P. MIFRI-Two and Three-Dimensional Crystallographic Fourier Surmation Program for the IBM 704 Computer, M.I.T., Cambridge, Massachusetts, 1960.
Smits, D. W. and Wiebenga, E. H.Acta Cryst., 1953,6, 531.
Srinivasan, R...Proc. Indian Acad. Sci., 1959a,49 A, 340.
—..Ibid, 1959b,50 A, 19.
Stewart, R. F., Davidson, E. R. and Simpson, W. T.J. Chem. Phys., 1965,42, 169.
Vainshtain, B. K. and Gurskaya, G. V.Dokl. Akad. Nauk. SSSR, 1964,156, 312.
Wilson, A. J. C...Nature, 1942,150, 151.
Author information
Authors and Affiliations
Additional information
(Communicated by Dr. S. Ramaseshan,f.a.sc.)
Rights and permissions
About this article
Cite this article
Becker, J.W., Thathachari, Y.T. & Simpson, P.G. The crystal and molecular structure of 3, 4-dihydroxy L-phenyl-alanine. Proc. Indian Acad. Sci. 77, 99–129 (1973). https://doi.org/10.1007/BF03049513
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF03049513