Crystal and Molecular Structure of ω-Amino Acids, ω-Amino-Sulfonic Acids and Their Derivatives. VII. The Crystal and Molecular Structure of DL-Carnitine Hydrochloride

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概要

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• The crystal structure of DL-carnitine hydrochloride, C<SUB>7</SUB>H<SUB>15</SUB>NO<SUB>3</SUB>·HCl, was determined by the heavy atom method using X-ray diffraction data on a Weissenberg photograph, and refined by the least-squares method to an <I>R</I>-factor of 0.13 for 1969 independent reflections. The crystals are monoclinic space group P2<SUB>1</SUB>⁄<I>c</I>, <I>Z</I>=4, with <I>a</I>=6.77(1), <I>b</I>=11.41(2), <I>c</I>=15.10(3) Å and β=120.1(1)°. By protonation at carboxyl oxygen atom, carnitine molecule has the cationic form, N<SUP>+</SUP>(CH<SUB>3</SUB>)<SUB>3</SUB>CH<SUB>2</SUB>CH(OH)CH<SUB>2</SUB>COOH, with <I>trans</I>-<I>zigzag</I> skeletal configuration as similar as γ-amino-β-hydroxybutyric acid. The Cl<SUP>−</SUP> ion mediates between adjacent carnitine cations by two O–H···Cl<SUP>−</SUP> hydrogen bonds to form infinite chain elongated along the <I>c</I>-axis. The correlation between molecular structure and biological activity was also discussed.

• 公益社団法人 日本化学会の論文

著者

• Fujiwara Takaji

  Faculty Of Pharmaceutical Sciences Of Osaka University

• TOMITA Ken-ichi

  Faculty of Pharmaceutical Sciences of Osaka University

• Kim Yang

  Faculty of Pharmaceutical Sciences, Osaka University

• Urabe Keiko

  Faculty of Pharmaceutical Sciences, Osaka University

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