Optical Resolution, Characterization, and X-Ray Crystal Structures of Diastereomeric Salts of Chiral Amino Acids with (S)-(-)-1-Phenylethanesulfonic Acid.
Optical Resolution, Characterization, and X-Ray Crystal Structures of Diastereomeric Salts of Chiral Amino Acids with (S)-(-)-1-Phenylethanesulfonic Acid.
复制标题
手性氨基酸与 (S)-(-)-1-苯基乙磺酸的非对映体盐的光学分辨率、表征和 X 射线晶体结构。
DOI：
10.1246/bcsj.67.3012
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发表时间：
1994
影响因子：
4
通讯作者：
M. Senuma
中科院分区：
文献类型：
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作者：
R. Yoshioka;Osamu Ohtsuki;T. Date;K. Okamura;M. Senuma
十种 DL-氨基酸 (AA)，包括中性和碱性氨基酸以及亚氨基酸，通过在各种溶剂中用 (−)-1-苯基乙磺酸 (PES) 分步结晶其非对映体盐，进行光学拆分，无需衍生化为其共价化合物。通过DSC和光谱分析了拆分过程中形成的几对非对映晶体盐，结果表明成功的拆分归因于溶解度较高的D-AA·(−)-PES和溶解度较低的L-AA·(−)-PES之间的各种物理化学性质的差异。通过比较 D- 和 L-HPG·(−)-PES 的 X 射线晶体结构，探索了最成功解析的物质 DL-对羟基苯基甘氨酸 (HPG) 盐的手性识别。两种晶体结构在氢键网络方面存在明显差异：溶解度较低的L-HPG·(−)-PES仅具有通过对羟基以“头尾”排列的强氢键连接的HPG无限链，...
Ten DL-Amino acids (AA), including neutral, and basic amino acids, and an imino acid, were optically resolved, without derivatization into their covalent compounds, by means of fractional crystallization of their diastereomeric salts with (−)-1-phenylethanesulfonic acid (PES) in various solvents. Several pairs of the diastereomeric crystalline salts formed during the resolutions were analyzed by DSC and spectroscopy, which showed that the successful resolutions were attributable to differences in various physicochemical properties between the more-soluble D-AA·(−)-PES and less-soluble L-AA·(−)-PES. Chiral recognition of the most successfully resolved species, DL-p-hydroxyphenylglycine (HPG) salt, was explored by comparing the X-ray crystal structures of D- and L-HPG·(−)-PES. The two crystal structures differed obviously in their hydrogen-bonding networks: the less-soluble L-HPG·(−)-PES only had strong hydrogen-bonded infinite chains of HPG in a “head-to-tail” arrangement through the p-hydroxyl group, the ...
Inoue,M.：“在职业和环境健康中压力和情绪的控制机制：基于神经内分泌的研究中，孤束核的激活使血液在中枢神经系统和其他器官之间反向流动。”
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