2019
DOI: 10.1002/chem.201903032
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Chiral Induction and Remote Chiral Communication in Quinoline Oligoamide Foldamers for Determination of Enantiomeric Excess and Absolute Configuration of Chiral Amines and Their Derivatives

Abstract: Twop entameric foldamers, Q5 and Q5C-S,c ontaining aC ÀFbond were synthesized based on quinoline oligamidef oldamers for the measurement of enantiomeric excess and for the determination of absolute configuration of chiral amines, diamines, amino alcohols, and a-amino acid esters. Chiral induction of Q5 was triggered in situ when the chiral analytes reacted with the CÀFb ond in Q5 by aN -nucleophilic substitution reaction, leading to al inear correlation between the CD amplitude at the regiono fq uinoline chrom… Show more

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Cited by 12 publications
(6 citation statements)
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“…To find the proof of hydrogen bonds on the helix-sense bias of foldamer, Zheng [9] et al had synthesized the other foldamer 2 , in foldamer 2 , hydrogen bond O-H-N A is formed between terminal group and quinoline-based amine (Figure 5). However, they found that the hydrogen bond O-H-N A cannot enhance the helix-sense bias of foldamer.…”
Section: ηελιξ ηανδεδνεσς οφ β-πινενε-δερι εδ πψριδψλ αμινε συβστιτυτ...mentioning
confidence: 99%
See 1 more Smart Citation
“…To find the proof of hydrogen bonds on the helix-sense bias of foldamer, Zheng [9] et al had synthesized the other foldamer 2 , in foldamer 2 , hydrogen bond O-H-N A is formed between terminal group and quinoline-based amine (Figure 5). However, they found that the hydrogen bond O-H-N A cannot enhance the helix-sense bias of foldamer.…”
Section: ηελιξ ηανδεδνεσς οφ β-πινενε-δερι εδ πψριδψλ αμινε συβστιτυτ...mentioning
confidence: 99%
“…Therefore, a lot of study has been reported on enantio-selective ofβ -pinene derived molecular [7,8] . In 2017, the study that β -pinene-derived pyridyl group can induce the handedness of oligoamide foldamers has been reported [9] . Experimental data has shown thatβ -pinene-derived pyridyl connecting with quinoline oligoamide behave better selection of handedness at N-terminal than at C-terminals.…”
Section: Introductionmentioning
confidence: 99%
“…其中, 酰胺键是 有效识别离子对的唯一官能团. 袁立华等 [95] 除大环化合物外, 寡聚芳酰胺折叠体也能用于离子 或分子识别 [96][97][98] . 例如, 黎占亭等 [97] 下, 寡聚芳香酰胺形成稳定的折叠构象.…”
Section: 离子和分子识别unclassified
“…其中, 五聚体 82d 具有最大的结合能力(K a =360 L•mol -1 , CDCl 3 ). 江 华等 [98] 3.3 跨膜通道 人们在研究生物跨膜通道的基础上, 利用非天然分 子模仿并制备了许多人工跨膜通道, 用于输送生物活性 的离子、小分子及生物大分子等, 其中具有孔隙结构的 刚性寡聚芳酰胺大环以及折叠体的自组装是构筑跨膜 通道最常用的一种方法. 龚兵等 [99] 设计合成了基于分 子内三中心氢键的刚性芳酰胺大环 85, 其能够在脂质 双分子层中自组装成离子通道, 且该通道对 Na + 和 K + 具有良好的传输性能(图 24).…”
Section: 离子和分子识别unclassified
“…Therefore, many studies have reported on the enantio‐selection of β ‐pinene‐derived molecules [7, 8]. In 2017, a study showed that the β ‐pinene‐derived pyridyl group can induce the handedness of oligoamide foldamers [9]. Experimental data have shown that β ‐pinene‐derived pyridyl connected with quinoline oligoamide exhibits better selection of handedness at N‐terminus than at C‐terminus.…”
Section: Introductionmentioning
confidence: 99%