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Molecular mechanics-based conformational analysis of previtamin D and its A-ring analogues

Konformationsanalyse von Previtamin D und seiner A-Ring-Analogen mit Hilfe von Kraftfeldrechnungen

  • Organische Chemie Und Biochemie
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Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Summary

The ground-state conformational analysis of previtamin D and analogues with different substituents at C-3, C-1, and C-10 have been performed by force-field calculations. Differences in the photochemistry of these analogues are discussed in view of the concept of ground-state conformational control in photochemical reactions. The effect of complexes of previtamin D with silanol derivatives, formedvia hydrogen bonds, on their conformational equilibrium has been calculated. An increase in the population ofcZc conformers with increasing size of the silanol molecules (as a model for a heterogeneous silica surface) was observed.

Zusammenfassung

Eine Konformationsanalyse des Grundzustandes von Previtamin D and von an C-1, C-3 und C-10 substituierten Analogen wurde mit Hilfe von Kraftfeldrechnungen durchgeführt. Unterschiedliches Reaktionsverhalten bei den photochemischen Umsetzungen dieser Verbindungen werden unter dem Gesichtspunkt der Grundzustandskontrolle von photochemischen Reaktionen diskutiert. Der Einfluß von Komplexbildung über Wasserstoffbrücken von Previtamin D mit Silanolen wurde berechnet. Eine Zunahme der Population dercZc-Konformeren mit zunehmender Größe des Silanols (ein Modell für eine heterogene Kieselgeloberfläche) wurde dabei beobachtet.

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Authors and Affiliations

  1. Institute of Surface Chemistry, National Ukrainian Academy of Sciences, 252022, Kiev, Ukraine

    O. Dmitrenko

  2. Institute of Organic Chemistry, University of Vienna, A-1090, Vienna, Austria

    W. Reischl

Authors
  1. O. Dmitrenko
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  2. W. Reischl
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Dmitrenko, O., Reischl, W. Molecular mechanics-based conformational analysis of previtamin D and its A-ring analogues. Monatsh Chem 127, 445–453 (1996). https://doi.org/10.1007/BF00810887

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  • DOI: https://doi.org/10.1007/BF00810887

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