Abstract
α-Hydroxymethyltyrosine has been synthesized by a route involvingα-hydroxymethylation. Dextrorotatory N-benzoyl-α-hydroxymethyltyrosine4 crystallizes in space group P212121 with cell parameters:a=13.2266(9),b=16.1099(9),c=7.4475(5) Å,V=15.86.9(2) Å3,Z=4. The structure was solved by direct methods and refined toR=0.047 andR w =0.066 with 1549 independent and 956\(\overline {hkl}\) reflections. The absolute configuration of 1 was determined asR by the application of Hamilton test and by the estimation of the Bijvoet coefficientB. Just as in N-benzoyl-α-methylcysteine (Wieczorek et al., 1989), theα-amino acid residue adopts the C5 ring conformation similar to the fully extended form. The two side chains also adopt an extended conformation around the Cα atom.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
Ashida, T., Tsunogae, Y., Tanaka, J., and Yamane, F. (1987)Acta Crystallogr. B 43, 212.
Beurskens, G., Noordik, J. M., and Beurskens, P. T. (1980)Cryst. Struct. Comm. 9, 23.
Cahn, R. S., Ingold, C., and Prelog, V. (1966)Angev. Chem. 78, 413.
Dunitz, J. D. (1976)X-Ray Analysis and the Structure of Organic Molecules (Cornell University Press, Ithaca and London), p. 331.
Hamilton, W. C. (1965)Acta Crystallogr. 18, 502.
Kamiński, Z. J., Leplawy, M. T., and Zabrocki, J. (1973)Synthesis 791.
Kollonitsch, J., Patchett, A. A., Marburg, S., Maycock, A., Perkins, L. M., Doldouras, G. A., Duggan, D. E., Aster, S. D. (1978)Nature (London) 274, 906.
Motherwell, W. P. S. (1976)Pluto, a program for plotting molecular and crystal structures (Cambridge University, England).
Nardelli, M. (1983) Comput. Chem.7, 95.
Paterson, Y., Rumsey, S. M., Benedett, E., Nemethy, G., and Scheraga, H. A. (1981)J. Am. Chem. Soc. 103, 2947.
Pearson, E. S., and Hartley, H. O. (1966)Biometrica Tables for Statisticians (third edition), Vol. 1, Table 18 (Cambridge Univ. Press).
Rogers, D. (1981)Acta Crystallogr. A 37, 734.
Sheldrick, G. M. (1976)Shelx, a program for crystal structure determination. (Cambridge University, England).
Sheldrick, G. M. (1986)Shelxs, a program for crystal structure determination. (Cambridge University, England).
Schnettler, R. A., Such, J. T., and Dage, R. C. (1976)J. Med. Chem. 19, 191.
Wieczorek, W., Bukowska-Strzyżewska, M., Olma, A., and Leplawy, M. T. (1989)J. Crystallogr. Spectrosc. Res. 19, 257.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Wieczorek, W., Bukowska-Strzyżewska, M., Leplawy, M.T. et al. Synthesis and absolute configuration of (+) α-hydroxymethyltyrosine by X-ray analysis of its N-benzoyl derivative. Journal of Crystallographic and Spectroscopic Research 21, 209–215 (1991). https://doi.org/10.1007/BF01161067
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF01161067