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Synthesis of camphor sulfonic acid derivatives modified Mg/Al-LDH for efficient separation of propranolol enantiomers
Abstract Designing chiral adsorption separation material with high enantioselectivity and stability is a promising route to realize the enantioselective recognition and separation of racemic molecules. Here, for the first time, camphor sulfonic acid derivatives (CSA) were synthesized as a chiral resolving agent, and it was modified on Mg/Al layered double hydroxide (Mg/Al-LDH) through electrostatic self-assembly to construct functionalized chiral adsorption separation material (CSA@LDH), which could be served as an adsorbent for enantioselective recognition and separation of propranolol enantiomers (R,S-PRO). The CSA@LDH maintained the advantage of limited chiral space in layered structures to achieve the selective enrichment of R-PRO, and the e.e.% value of single separation could reach 19.5%. Meanwhile, density functional theory (DFT) calculations supported that chiral recognition and separation were ascribed to the discrepancy in affinities stemming from the difference of π-π interaction force and hydrogen bonding capacity of CSA with R,S-PRO. Hence, considering the superior ability of hydrogen bond coordination and stereocontrol of camphor sulfonic acid derivatives, it is expected to be more widely used as a chiral resolving agent for other enantiomeric recognition and separation.
Graphical abstract Display Omitted
Highlights Camphor sulfonic acid derivatives (CSA) was first synthesized. CSA@LDH was constructed as novel chiral adsorbents to separate R,S-PRO. The absorbent realized the selective enrichment of R-propranolol. The e.e.% value of single separation was 19.5%. CSA would expand to other enantiomeric recognition and separation.
Synthesis of camphor sulfonic acid derivatives modified Mg/Al-LDH for efficient separation of propranolol enantiomers
Abstract Designing chiral adsorption separation material with high enantioselectivity and stability is a promising route to realize the enantioselective recognition and separation of racemic molecules. Here, for the first time, camphor sulfonic acid derivatives (CSA) were synthesized as a chiral resolving agent, and it was modified on Mg/Al layered double hydroxide (Mg/Al-LDH) through electrostatic self-assembly to construct functionalized chiral adsorption separation material (CSA@LDH), which could be served as an adsorbent for enantioselective recognition and separation of propranolol enantiomers (R,S-PRO). The CSA@LDH maintained the advantage of limited chiral space in layered structures to achieve the selective enrichment of R-PRO, and the e.e.% value of single separation could reach 19.5%. Meanwhile, density functional theory (DFT) calculations supported that chiral recognition and separation were ascribed to the discrepancy in affinities stemming from the difference of π-π interaction force and hydrogen bonding capacity of CSA with R,S-PRO. Hence, considering the superior ability of hydrogen bond coordination and stereocontrol of camphor sulfonic acid derivatives, it is expected to be more widely used as a chiral resolving agent for other enantiomeric recognition and separation.
Graphical abstract Display Omitted
Highlights Camphor sulfonic acid derivatives (CSA) was first synthesized. CSA@LDH was constructed as novel chiral adsorbents to separate R,S-PRO. The absorbent realized the selective enrichment of R-propranolol. The e.e.% value of single separation was 19.5%. CSA would expand to other enantiomeric recognition and separation.
Synthesis of camphor sulfonic acid derivatives modified Mg/Al-LDH for efficient separation of propranolol enantiomers
Yuan, Tianqi (author) / Chen, Miao (author) / Sun, Xiaotong (author) / Guan, Jianping (author) / Zhu, Fawei (author) / Tang, Kai (author) / Zhang, Zhipeng (author) / Liu, Qi (author) / Chen, Xiaoqing (author)
Applied Clay Science ; 224
2022-04-14
Article (Journal)
Electronic Resource
English
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