Structural Studies of Tryptophan Metabolites by X-ray Diffraction Method. I. The Crystal and Molecular Structure of 5-Hydroxy-DL-Tryptophan

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概要

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• 5-Hydroxy-DL-tryptophan was crystallized from a methanol solution in the monoclinic space group C2/c, with cell-dimensions of <I>a</I>=16.765, <I>b</I>=5.892, <I>c</I>=20.887 Å, and β=92.06°. The molecular structure and stereoconfiguration have been elucidated by the direct method for non-primitive space group. A Fourier map, calculated with the largest 198 normalized structure factors as Fourier coefficients, revealed the whole structure which was refined by the least-squares method. The molecule is a zwitterion as in the crystal structure of amino acids, each amino nitrogen atom having an extra proton. The indole ring plane forms a dihedral angle of 40° with that formed by an acid group. With respect to the conformation about the C(α)–C(β) bond, the orientation of C(β)–C(γ) bond is <I>trans</I> with respect to the C(α)–COO–. The molecules are arranged in double layers parallel to the <I>ab</I>-plane. The layer by polar groups is held together by a series of hydrogen bonds in a three-dimensional network, and by non-polar groups in the other layer, indole rings being stacked by van der Waals forces. The D-and L-forms of 5-hydroxytryptophan are hydrogen-bonded into two types of dimer related by the center of symmetry, one through N–H···O, and the other through O–H···O hydrogen bonding.

• 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

• Wakahara Akio

  Faculty of Pharmaceutical Sciences, Osaka University

• Kido Masaru

  Faculty of Pharmaceutical Sciences, Osaka University

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