Skip to main content
Log in

Ground-state conformational equilibrium of previtamin D and its E-isomer: Effect on the absorption characteristics

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

The ground-state conformational analysis of previtamin D, its E-isomer, tachysterol, their 10-desmethyl analogues and 1-methyl-1-hydroxy-previtamins have been performed by force-field calculations. Differences in the absorption characteristics of these compounds are discussed in view of the chromophore geometry and abundance (%) of the calculated conformers according to a Boltzmann distribution at 298 K. On the basis of present calculations, the red shift of previtamin D low-temperature UV and CD spectra determined earlier is attributed to the shift of conformational equilibrium in favour of more stable cZc geometries. The effect of complex formation with simplest model cluster of silica surface ((H3SiO)3SiOH), on previtamin D and tachysterol conformational equilibria and on UV-absorbance maxima has been evaluated.

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.

Institutional subscriptions

Similar content being viewed by others

References

  1. H.J.C. Jacobs and E. Havinga, Adv. Photochem. 11, 305 (1979). b) F. Bernardi, M. Olivucci, I.N. Ragazos, and M.A. Robb, J. Am. Chem. Soc. 114, 8211 (1992).

    Article  CAS  Google Scholar 

  2. O. Dmitrenko and W. Reischl, Monatshefte für Chemie 127, 445 (1996).

    Article  CAS  Google Scholar 

  3. R. Wilbrandt and F.W. Langkilge. In: Structures and Conformations of Non-Rigid Molecules, J. Laane et al. (Eds.), Kluwer Academic Publishers, 1993, p. 567. b) U. Mazzucato and F. Momicchioli, Chem. Rev. 91, 1679 (1991).

  4. R.B. Koolstra, J. Cornelisse, and H.J.C. Jacobs, Recl. Trav. Chim. Pays-Bas 106, 526 (1987).

    CAS  Google Scholar 

  5. H. Ishida, M. Shimizu, K. Yamamoto, Y. Iwasaki, and S. Yamada, J. Org. Chem. 60, 1828 (1995).

    Article  CAS  Google Scholar 

  6. O.G. Perminova, Ph.D. Thesis, Kiev, 1990 (in Russian).

  7. G MMX and PC-MODEL (Serena Software, Bloomington, Indiana) for SGI Indigo 2.-MMP2 (QCPE 395) for the IBM 3090 mainframe computer.-N.L. Allinger and H.L. Flanagan, J. Comput. Chem. 4, 399 (1983).

    Google Scholar 

  8. W.G. Dauben and D.J.H. Funhoff, J. Org. Chem. 53, 5070 (1988).

    Article  CAS  Google Scholar 

  9. E.L. Eliel, N.L. Allinger, S.J. Angyal, and G.A. Morrison, Conformational Analysis, Interscience, New York, 1965, p. 102.

    Google Scholar 

  10. O. Hofer, H. Kählig, and W. Reischl, Monatshefte für Chemie 124, 185 (1993).

    Article  CAS  Google Scholar 

  11. W. Klyne and V. Prelog, Exerientia 12, 521 (1960).

    Article  Google Scholar 

  12. E. Berman, N. Friedman, Y. Mazur, M. Sheves, Z.V. Zaretskii, I. Proc. Workshop Vitam. D, 4th, 1979, 65.

  13. P.A. Maessen, Ph.D. Thesis, Leiden, 1983.

  14. J. Lugtenburg and E. Havinga, Tetrahedron Lett. 2391 (1969).

  15. K.H. Pfoertner and M. Voelker, J. Chem. Soc. Perkin Trans. 2 527 (1991).

    Google Scholar 

  16. P.A. Maessen, H.J.C. Jacobs, J. Cornelisse, and E. Havinga, Angewandte Chemie 95, 752 (1983).

    Article  CAS  Google Scholar 

  17. V. Malatesta, C. Willis, and P.A. Hackett, J. Am. Chem. Soc. 103, 6781 (1981).

    Article  CAS  Google Scholar 

  18. I.B. Berlman, Phys. Chem. 74(16), 3085 (1970).

    Article  CAS  Google Scholar 

  19. J. Sauer, P. Ugliengo, E. Garrone, and V.R. Saunders, Chem. Rev. 94, 2095 (1994).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Dmitrenko, O., Reischl, W. Ground-state conformational equilibrium of previtamin D and its E-isomer: Effect on the absorption characteristics. Res. Chem. Intermed. 23, 691–702 (1997). https://doi.org/10.1163/156856797X00484

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1163/156856797X00484

Keywords

Navigation