GR 24 enantiomers: synthesis, NMR spectroscopy, X-ray crystallography, and separation by chiral electrokinetic capillary chromatography.
GR 24 enantiomers: synthesis, NMR spectroscopy, X-ray crystallography, and separation by chiral electrokinetic capillary chromatography.
复制标题
GR 24 对映体：合成、NMR 光谱、X 射线晶体学和手性电动毛细管色谱分离。
DOI：
10.1021/ac991438o
复制
发表时间：
2000
影响因子：
7.4
通讯作者：
Warner,IM
中科院分区：
文献类型：
--
作者：
Rugutt,JK;Yarabe,HH;Shamsi,SA;Billodeaux,DR;Fronczek,FR;Warner,IM
利用手性高分子表面活性剂毛细管电泳（CPSCE）研究了三种高分子手性表面活性剂（PCS）对2-甲基-4-（2-氧代-2,3,3a,8b-四氢-4H-茚并[1,2b]呋喃-3-亚基甲氧基）but-2-en-4-olide（俗称GR 24）对映体的手性判别。 CPSCE 结果表明，PCS 主链上缬氨酸残基的光学构型影响 GR24 立体异构体的手性分辨率和洗脱顺序。聚(N-十一酰基缬氨酸钠)的Thel-和d-形式提供所有四种对映体的基线分离，而thedl-形式分离GR 24的非对映体(1)。提出了一个模型，合理化 CPSCE 中 1 的迁移行为和手性拆分。 GR 24 和 3-[(2,5-二氢-3-甲基-2-氧代-5-呋喃基)氧代]亚甲基-3,3a,6,6a-四氢-2H-环戊[b]呋喃-2-酮 (GR 7) 立体中心的实际构型是通过高分辨率核磁共振波谱和 X 射线晶体学的协同应用建立的。
Chiral discrimination of enantiomers of 2-methyl-4-(2-oxo-2,3,3a,8b-tetrahydro-4H-indeno[1,2b]furan-3-ylidenemethoxy)but-2-en-4-olide (commonly referred to as GR 24) by three polymeric chiral surfactants (PCS) is studied by use of chiral polymeric surfactant capillary electrophoresis (CPSCE). The CPSCE results indicate that the optical configurations of valine residues on the PCS backbone affect chiral resolution and elution order of GR24 stereoisomers. Thel- andd-forms of poly(sodiumN-undecanoyl valinate) provide baseline separation of all four enantiomers while thedl-form separates diastereomers of GR 24 (1). A model is presented rationalizing the migration behavior and chiral resolution of1in CPSCE. The actual configuration of the stereogenic centers of GR 24 and 3-[(2,5-dihydro-3-methyl-2-oxo-5-furanyl)oxo]methylene-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-2-one (GR 7) is established by a concerted application of high-resolution nuclear magnetic resonance spectroscopy and X-ray crystallography.