Acta Chimica Sinica ›› 2023, Vol. 81 ›› Issue (1): 20-28.DOI: 10.6023/A22090400 Previous Articles Next Articles
Article
投稿日期:
2022-09-25
发布日期:
2022-12-12
基金资助:
Xiaomao Tian, Yuequn Lin, Han Zhu, Chao Huang(), Bixue Zhu(
)
Received:
2022-09-25
Published:
2022-12-12
Contact:
*E-mail: Supported by:
Share
Xiaomao Tian, Yuequn Lin, Han Zhu, Chao Huang, Bixue Zhu. Enantiomers Identification of Penicillamine by Chiral Mono-Schiff Base Macrocycles[J]. Acta Chimica Sinica, 2023, 81(1): 20-28.
Host-guest | KD (D-Pen) | KL (L-Pen) | KL/KD | KD/KL |
---|---|---|---|---|
CR-pen | 2.12×107 | 3.44×107 | 1.62 | 0.61 |
CS-pen | 3.20×107 | 1.77×107 | 0.55 | 1.81 |
Host-guest | KD (D-Pen) | KL (L-Pen) | KL/KD | KD/KL |
---|---|---|---|---|
CR-pen | 2.12×107 | 3.44×107 | 1.62 | 0.61 |
CS-pen | 3.20×107 | 1.77×107 | 0.55 | 1.81 |
[1] |
Xiao, T.; Li, S.; Zhang, X.; Lin, C.; Wang, L. Y. Chin. J. Chem. 2013, 31, 627.
doi: 10.1002/cjoc.201300246 |
[2] |
Geer, M. F.; Walla, M.; Solntsev, K.; Strassert, C.; Shimizu, L. S. J. Org. Chem. 2013, 78, 5568.
doi: 10.1021/jo400685u |
[3] |
Radujević, A.; Penavic, A.; Pavlović, R. Z.; Badjić, J. D.; Anzenbacher, P. Chem 2022, 8, 2228.
doi: 10.1016/j.chempr.2022.05.010 |
[4] |
Wang, D.; You, L.; Wang, J.; Wang, H.; Zhang, D.; Li, Z. T. Tetrahedron Lett. 2013, 54, 6967.
doi: 10.1016/j.tetlet.2013.10.064 |
[5] |
María, D.; Claramunt, R.; Torralba, M.; Torres, M.; Elguero, J. Tetrahedron Lett. 2019, 60, 1206.
doi: 10.1016/j.tetlet.2019.03.066 |
[6] |
Wei, X. K.; Gu, J. C.; Liu, X. L.; Huang, C.; Zhu, B. X. Chin. J. Org. Chem. 2018, 38, 3386. (in Chinese)
doi: 10.6023/cjoc201805012 |
( 魏小康, 谷静池, 刘兴丽, 黄超, 朱必学, 有机化学, 2018, 38, 3386.)
doi: 10.6023/cjoc201805012 |
|
[7] |
Xiong, Y.; Huang, C.; Liu, H. J.; Yi, R.; Zhu, B. X.; Ni, X. L. Chin. Chem. Lett. 2021, 32, 3522.
doi: 10.1016/j.cclet.2021.04.060 |
[8] |
Li, D. H.; Smith, B. D. Beilstein J. Org. Chem. 2019, 15, 1086.
doi: 10.3762/bjoc.15.105 |
[9] |
Barisic, D.; Lesic, F.; Vlasic, M. T.; Uzarevic, K.; Bregovic, N.; Tomisi, V. Tetrahedron 2022, 120, 132875.
doi: 10.1016/j.tet.2022.132875 |
[10] |
Tromans, R. A.; Carter, T. S.; Chabanne, L.; Crump, M. P.; Li, H. Y.; Matlock, J. V.; Orchard, M. G.; Davis, A. P. Nat. Chem. 2019, 11, 52.
doi: 10.1038/s41557-018-0155-z pmid: 30420776 |
[11] |
Roth, J. Chem. Rev. 2002, 102, 285.
doi: 10.1021/cr000423j |
[12] |
Glavin, D. P.; Burton, A. S.; Elsila, J. E.; Aponte, J. C.; Dworkin, J. P. Chem. Rev. 2019, 120, 4660.
doi: 10.1021/acs.chemrev.9b00474 |
[13] |
Lu, H. J.; Yu, C. T.; Guo, Y. L. Acta Chim. Sinica 2002, 60, 882. (in Chinese)
|
( 陆豪杰, 余翀天, 郭寅龙, 化学学报, 2002, 60, 882.)
|
|
[14] |
Li, D.; Gao, B. J.; Xu, W. M. Acta Chim. Sinica 2011, 69, 3019 (in Chinese)
|
( 李丁, 高保娇, 许文梅, 化学学报, 2011, 69, 3019.)
doi: 10.6023/A1106192 |
|
[15] |
Liu, Z.; Zhang, S.; Cheng, M.; Yang, L.; Li, G.; Xu, W. W.; Qu, H. N.; Liang, F.; Cheng, J.; Li, H. B. Analyst 2022, 147, 1803.
doi: 10.1039/D2AN00310D |
[16] |
Zhu, B. X.; Ruan, W. J.; Gao, F.; Hu, G. H.; Zhu, Z. A. Acta Chim. Sinica 2004, 62, 58. (in Chinese)
|
( 朱必学, 阮文娟, 高峰, 胡国航, 朱志昂, 化学学报, 2004, 62, 58.)
|
|
[17] |
Liu, T.; Ruan, W. J.; Nan, J.; Zhu, Z. A. Chin. J. Chem. 2003, 21, 751.
doi: 10.1002/cjoc.20030210709 |
[18] |
Forte, G.; Sfrazzetto, G. T.; Pappalardo, A. Comput. Theor. Chem. 2015, 1068, 8.
doi: 10.1016/j.comptc.2015.06.007 |
[19] |
Ikbal, S. A.; Sakata, Y.; Akine, S. Dalton Trans. 2021, 50, 4119.
doi: 10.1039/d1dt00218j pmid: 33662079 |
[20] |
Peluso, P.; Chankvetadze, B. Chem. Rev. 2022, 122, 13235.
doi: 10.1021/acs.chemrev.1c00846 pmid: 35917234 |
[21] |
Rajasekar, P.; Jose, C.; Sarkar, M.; Boomishankar, R. Angew. Chem. Int. Ed. 2021, 60, 4023.
doi: 10.1002/anie.202012392 |
[22] |
Wang, S. Y.; Li, L.; Xiao, Y.; Wang, Y. Trends Anal. Chem. 2019, 121, 115691.
doi: 10.1016/j.trac.2019.115691 |
[23] |
Padovani, D.; Galardon, E. Chem. Res. Toxicol. 2022, 35, 412.
doi: 10.1021/acs.chemrestox.1c00313 |
[24] |
Durán, G. M.; Abellán, C.; Contento, A. M.; Ríos, Á. Microchim. Acta 2017, 184, 815.
doi: 10.1007/s00604-017-2074-x |
[25] |
Mendes, J.; Almeida, K. J.; Neto, J. L.; Ramalho, T. C.; Duarte, H. A. J. Spectrochim. Acta Part A: Mol. Biomol. Spectrosc. 2017, 184, 308.
doi: 10.1016/j.saa.2017.05.025 |
[26] |
Yang, N.; Zhang, K.; Guan, Q. W.; Wang, Z. J.; Chen, K. N.; Mao, X. Y. Antioxidants 2022, 11, 1602.
doi: 10.3390/antiox11081602 |
[27] |
Zhang, Y.; Wang, H. Y.; He, X. W.; Li, W. Y.; Zhang, Y. K. J. Hazard. Mater. 2021, 412, 125249.
doi: 10.1016/j.jhazmat.2021.125249 |
[28] |
Sun, L.; Huang, F.; Liu, W. W.; Lin, L.; Hong, Y.; Kong, X. L. Spectrochim. Acta Part A: Mol. Biomol. Spectrosc. 2020, 241, 118653.
doi: 10.1016/j.saa.2020.118653 |
[29] |
Li, Z. B.; Lin, J.; Pu, L. Angew. Chem. Int. Ed. 2005, 44, 1690.
doi: 10.1002/anie.200462471 |
[30] |
Zhu, Y. Y.; Wu, X. D.; Gu, S. H.; Pu, L. J. Am. Chem. Soc. 2019, 141, 175.
doi: 10.1021/jacs.8b07803 |
[31] |
Pu, L. Chem. Commun. 2022, 58, 8038.
doi: 10.1039/D2CC02363F |
[32] |
Dong, J. Q.; Tan, C. X.; Zhang, K.; Liu, Y.; Low, P. J.; Jiang, J. W.; Cui, Y. J. Am. Chem. Soc. 2017, 139, 1554.
doi: 10.1021/jacs.6b11422 |
[33] |
Gangemi, C. M. A.; Rimkaite, U.; Cipria, F.; Sfrazzetto, G. T.; Pappalardo, A. Front. Chem. 2019, 7, 836.
doi: 10.3389/fchem.2019.00836 pmid: 31850322 |
[34] |
Yang, S. T.; Wu, F. L.; Yu, F. Z.; Gu, L. C.; Wang, H. H.; Liu, Y. Y.; Chu, Y. Q.; Wang, F. Y.; Fang, X.; Ding, C. F. Anal. Chim. Acta 2021, 1184, 339017.
doi: 10.1016/j.aca.2021.339017 |
[35] |
Ema, T.; Yamasaki, T.; Watanabe, S.; Hiyoshi, M.; Takaishi, K. J. Org. Chem. 2018, 83, 10762.
doi: 10.1021/acs.joc.8b01327 |
[36] |
Wen, J.; Feng, L.; Zhao, H. M.; Zheng, L.; Stavropoulos, P.; Ai, L.; Zhang, J. X. J. Org. Chem. 2022, 87, 7934.
doi: 10.1021/acs.joc.2c00587 |
[37] |
Ohishi, Y.; Chiba, J.; Inouye, M. J. Org. Chem. 2022, 87, 10825.
doi: 10.1021/acs.joc.2c01095 pmid: 35938888 |
[38] |
Thordarson, P. Chem. Soc. Rev. 2011, 40, 1305.
doi: 10.1039/c0cs00062k pmid: 21125111 |
[39] |
Shi, M.; Qian, H. X. Tetrahedron 2005, 61, 4949.
doi: 10.1016/j.tet.2005.03.043 |
[40] |
Chen, Z. H.; Wu, C. T. Chin. J. Org. Chem. 2002, 22, 582. (in Chinese)
|
( 陈展虹, 吴成泰, 有机化学, 2002, 22, 582.)
|
[1] | Yeqiang Han, Bingfeng Shi. Palladium(II)-Catalyzed Enantioselective Functionalization of C(sp3)—H Bonds★ [J]. Acta Chimica Sinica, 2023, 81(11): 1522-1540. |
[2] | Pusu Yang, Chen-Xu Liu, Wen-Wen Zhang, Shu-Li You. Ir-Catalyzed Enantioselective Friedel-Crafts Type Allylic Substitution of Indolizines [J]. Acta Chimica Sinica, 2021, 79(6): 742-746. |
[3] | Zhuoji Deng, Yifan Ouyang, Yunlin Ao, Qian Cai. Copper(I)-Catalyzed Asymmetric Desymmetric Intramolecular Alkenyl C—N Coupling Reaction [J]. Acta Chimica Sinica, 2021, 79(5): 649-652. |
[4] | Bo Zhou, Renxiao Liang, Zhongyan Cao, Pinghai Zhou, Yixia Jia. Palladium-Catalyzed Heck Reaction of Endocyclic Conjugated C=C Bonds of Pyrroles [J]. Acta Chimica Sinica, 2021, 79(2): 176-179. |
[5] | Zhang Ronghua, Xu Bing, Zhang Zhanming, Zhang Junliang. Ming-Phos/Copper(I)-Catalyzed Asymmetric[3+2] Cycloaddition of Azomethine Ylides with Nitroalkenes [J]. Acta Chimica Sinica, 2020, 78(3): 245-249. |
[6] | Zhu Xuewei, Cui Xiaoyu, Cai Wensheng, Shao Xueguang. Temperature Dependent Near Infrared Spectroscopy for Understanding the Hydrogen Bonding of Amines [J]. Acta Chim. Sinica, 2018, 76(4): 298-302. |
[7] | LÜ Jian, Qin Yan, Cheng Jinpei, Luo Sanzhong. Counteranions of In(Ⅲ) Induced Reversal of Enantiocontrol in Friedel-Crafts Reaction of Indoles by Asymmetric Binary Acid Catalysis [J]. Acta Chimica Sinica, 2014, 72(7): 809-814. |
[8] | Zhou Rong, Xiao Wei, Yin Xiang, Zhan Gu, Chen Yingchun. Diastereo- and Enantioselective [4+2] Cycloadditions of Cyclic Enones with Cyclic 1-Azadienes [J]. Acta Chimica Sinica, 2014, 72(7): 862-866. |
[9] | Shi Zhuming, Song Yu, Lu Fang, Zhou Tianyou, Zhao Xin, Zhang Wenke, Li Zhanting. Evaluation on the Stability of the Intramolecular N—H…OMe Hydrogen Bonds of Aromatic Amide Foldamers [J]. Acta Chimica Sinica, 2013, 71(01): 51-61. |
[10] | TANG Ke-Wen, LI Hong-Jian, LIU Yong-Bing. Determination of Kinetics in Biphasic Recognition Chiral Extraction for Separation of Zopiclone Enantiomers [J]. Acta Chimica Sinica, 2011, 69(22): 2696-2702. |
[11] | XU Fei, ZHANG Lin-Qun, HE Li-Wei, GU Wei, FANG Fang, WU Qi-Nan, ZHAO Bo. Molecular Mechanism on the Interaction between Alisols and Human Serum Albumin [J]. Acta Chimica Sinica, 2011, 69(19): 2228-2234. |
[12] | CHEN Ying-Xin, GAO Bao-Jiao, JIANG Gui-Ming, ZHANG Rui-Xia. Constituting Chiral Caves by Using Novel Surface-Molecular Imprinting Technique and Realizating Chiral Separation of Enantiomers of Amino Acid [J]. Acta Chimica Sinica, 2011, 69(14): 1705-1714. |
[13] | MENG Chen-Peng, WANG Shun, ZHANG Ke-Jun, JIN Hui-Le, CHEN Xi-An, HU Mao-Lin, XIONG Jing. Electrochemical Study on the Interactions between Enantiomer of 2-(5-Fluorouracil-1-acetyl)amido-1,5-dimethyl Glutarate and Double-stranded/G-quadruplex DNA [J]. Acta Chimica Sinica, 2011, 69(10): 1173-1178. |
[14] | NIE Li, HU Lei, FU Xu-Cheng, JIANG Yun-Bao. Synthesis of N-(2,4-Dinitrophenyl)-N -(substituted-phenyl)hydrazones and Their Anion Sensing [J]. Acta Chimica Sinica, 2011, 69(01): 71-76. |
[15] | TONG Shang-Lun, HU Zhou, LIU Wei-Ping. Study on the Interaction between Paraquat and Calf Thymus DNA by Spectral Methods [J]. Acta Chimica Sinica, 2010, 68(14): 1404-1410. |
Viewed | ||||||
Full text |
|
|||||
Abstract |
|
|||||