Nono-Tagne Steve, Heinze Thomas, Gericke Martin, Otsuka Issei
Univ. Grenoble Alpes, CNRS, CERMAV, Grenoble, 38000, France.
Institute of Organic Chemistry and Macromolecular Chemistry, Friedrich-Schiller-University Jena, Humboldtstr 10, 07743, Jena, Germany.
Macromol Biosci. 2025 Mar;25(3):e2400415. doi: 10.1002/mabi.202400415. Epub 2024 Nov 27.
Electrospun nanofibrous membranes made of chiral selectors (CSs) have shown their potential for efficient chiral resolutions via filtrations. It is thus of great importance to expand the number of electrospun membranes made of various CSs for the resolution of a wide range of chiral compounds. Here, the electrospinning of two benzyl carbamate derivatives of cellulose, namely cellulose benzyl carbamate (CBzC) and cellulose 4-chlorobenzyl carbamate (CCBzC), to form a new type of enantioselective membranes for chiral resolutions of racemic compounds, is reported. The morphology of the electrospun membranes is studied by optical microscopy and scanning electron microscopy in relation to the electrospinning process parameters. Liquid-liquid permeation experiments of the racemic compounds, (R,S)-1-(1-naphthyl)ethanol ((R,S)-NET), (R,S)-1,1'-bi-2-naphtol ((R,S)-BNP), (R,S)-naproxen ((R,S)-NAP), and (R,S)-benzoin ((R,S)-BNZ) through the membranes demonstrate preferable permeations of (R)- or (S)-enantiomers depending on the combinations between the CSs and the racemates. Molecular docking simulations indicate the differences in the binding type, number, and free energies between the CSs and the enantiomers.
由手性选择剂（CSs）制成的电纺纳米纤维膜已显示出通过过滤实现高效手性拆分的潜力。因此，扩大由各种CSs制成的用于拆分多种手性化合物的电纺膜数量非常重要。在此，报道了纤维素的两种苄基氨基甲酸酯衍生物，即纤维素苄基氨基甲酸酯（CBzC）和纤维素4-氯苄基氨基甲酸酯（CCBzC）的电纺过程，以形成用于外消旋化合物手性拆分的新型对映选择性膜。通过光学显微镜和扫描电子显微镜研究了与电纺过程参数相关的电纺膜的形态。外消旋化合物（R,S）-1-（1-萘基）乙醇（（R,S）-NET）、（R,S）-1,1'-联-2-萘酚（（R,S）-BNP）、（R,S）-萘普生（（R,S）-NAP）和（R,S）-安息香（（R,S）-BNZ）通过这些膜的液-液渗透实验表明，根据CSs和外消旋体之间的组合，（R）-或（S）-对映体具有较好的渗透性。分子对接模拟表明了CSs与对映体之间在结合类型、数量和自由能方面的差异。
