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*

*この研究の対応する著者

研究成果査読

7 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)223-234
ページ数12
ジャーナルPhase Transitions
83
3
DOI
出版ステータスPublished - 2010 3

ASJC Scopus subject areas

  • 器械工学
  • 材料科学(全般)

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