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Enantioselective inclusion of pyrene-1-sulfonate salts of α-amino acids with crystals of α-cyclodextrin
Tetrahedron ( IF 2.1 ) Pub Date : 2020-03-04 , DOI: 10.1016/j.tet.2020.131100
Ikuko Miyoshi , Yuichi Kitamoto , Tetsuya Maeda , Naoya Morohashi , Tetsutaro Hattori

Enantioselective inclusion of α-amino acids with crystals of α-cyclodextrin (α-CD) has been achieved by converting the amino acids into sulfonate salts with pyrene-1-sulfonic acid (PyS). For example, crystals of α-CD selectively include l-leucine/PyS (1:1) salt in a host/guest ratio of ∼1 with 92%ee from a solution of the racemic salt in ethanol/N-methylformamide (91:9) at 40 °C. Under conditions optimized for individual amino acids, the PyS salts of valine, phenylalanine, and methionine are also included with good enantioselectivities (up to 86%ee). Mechanistic studies for the inclusion of leucine/PyS salt reveals that the enantioselectivity originates from the difference in stability between the inclusion complexes of D- and l-leucine/PyS salts with α-CD in crystals.



中文翻译:

α-氨基酸的-1--1磺酸盐与α-环糊精晶体的对选择性包容

的对映选择性包含α -氨基羧酸与晶体α环糊精(α -CD)已经由氨基酸转化成磺酸盐与芘-1-磺酸(PYS)来实现的。例如,α -CD的晶体选择性地含有约1的主体/客体比率的1-亮氨酸/ PyS(1:1)盐和来自消旋盐的乙醇/ N溶液的92%ee-甲基甲酰胺(91:9)在40°C下。在针对单个氨基酸优化的条件下,缬氨酸,苯丙氨酸和蛋氨酸的PyS盐也具有良好的对映选择性(最高86%ee)。对亮氨酸/ PyS盐包合物的机理研究表明,对映选择性源于D和1-亮氨酸/ PyS盐与α -CD包合物在晶体中稳定性的差异。

更新日期:2020-03-05
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