Evaluation of stability difference between asymmetric homochiral dimer in (S)-thalidomide crystal and symmetric heterochiral dimer in (RS)-thalidomide crystal

Toshiya Suzuki, Masahito Tanaka, Motoo Shiro, Norio Shibata, Tetsuya Osaka, Toru Asahi

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

Abstract

This article discusses differences in physicochemical properties such as solubility and melting point between (S)-thalidomide and (RS)-thalidomide based on crystal structures determined by X-ray diffraction experiments. Investigation of such differences is of great importance because thalidomide has attracted considerable attention again due to its wide-range bioactivity for intractable diseases. In this article, structures of hydrogen-bonded rings were compared between asymmetric homochiral dimers in (S)-thalidomide crystal and symmetric heterochiral dimers in (RS)-thalidomide crystal. The heterochiral dimer was evaluated to be more stable than the homochiral dimer by the energy calculations for hydrogen-bonded rings in those dimers. These results indicate that differences in physicochemical properties between enantiomeric and racemic thalidomides originate from the difference of structural stability between homochiral and heterochiral dimers.

Original languageEnglish
Pages (from-to)223-234
Number of pages12
JournalPhase Transitions
Volume83
Issue number3
DOIs
Publication statusPublished - 2010 Mar 1

Keywords

  • Energy calculation
  • Heterochiral dimer
  • Homochiral dimer
  • Hydrogen bond
  • Thalidomide
  • X-ray crystal structure analysis

ASJC Scopus subject areas

  • Instrumentation
  • Materials Science(all)

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