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 journalArticle

6 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

Fingerprint

Thalidomide
Dimers
dimers
Crystals
evaluation
crystals
Hydrogen
rings
structural stability
hydrogen
Bioactivity
melting points
Melting point
solubility
Solubility
Crystal structure
X ray diffraction
crystal structure
diffraction
x rays

Keywords

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

ASJC Scopus subject areas

  • Instrumentation
  • Materials Science(all)

Cite this

Evaluation of stability difference between asymmetric homochiral dimer in (S)-thalidomide crystal and symmetric heterochiral dimer in (RS)-thalidomide crystal. / Suzuki, Toshiya; Tanaka, Masahito; Shiro, Motoo; Shibata, Norio; Osaka, Tetsuya; Asahi, Toru.

In: Phase Transitions, Vol. 83, No. 3, 03.2010, p. 223-234.

Research output: Contribution to journalArticle

@article{b530215bb5c143d3befd02c4f1c1011e,
title = "Evaluation of stability difference between asymmetric homochiral dimer in (S)-thalidomide crystal and symmetric heterochiral dimer in (RS)-thalidomide crystal",
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.",
keywords = "Energy calculation, Heterochiral dimer, Homochiral dimer, Hydrogen bond, Thalidomide, X-ray crystal structure analysis",
author = "Toshiya Suzuki and Masahito Tanaka and Motoo Shiro and Norio Shibata and Tetsuya Osaka and Toru Asahi",
year = "2010",
month = "3",
doi = "10.1080/01411591003605986",
language = "English",
volume = "83",
pages = "223--234",
journal = "Phase Transitions",
issn = "0141-1594",
publisher = "Taylor and Francis Ltd.",
number = "3",

}

TY - JOUR

T1 - Evaluation of stability difference between asymmetric homochiral dimer in (S)-thalidomide crystal and symmetric heterochiral dimer in (RS)-thalidomide crystal

AU - Suzuki, Toshiya

AU - Tanaka, Masahito

AU - Shiro, Motoo

AU - Shibata, Norio

AU - Osaka, Tetsuya

AU - Asahi, Toru

PY - 2010/3

Y1 - 2010/3

N2 - 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.

AB - 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.

KW - Energy calculation

KW - Heterochiral dimer

KW - Homochiral dimer

KW - Hydrogen bond

KW - Thalidomide

KW - X-ray crystal structure analysis

UR - http://www.scopus.com/inward/record.url?scp=77951101106&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=77951101106&partnerID=8YFLogxK

U2 - 10.1080/01411591003605986

DO - 10.1080/01411591003605986

M3 - Article

VL - 83

SP - 223

EP - 234

JO - Phase Transitions

JF - Phase Transitions

SN - 0141-1594

IS - 3

ER -