Recognition of amphetamine/ibuprofen enantiomers by heterocyclic decapeptides
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- 英文论文题名：Recognition of amphetamine/ibuprofen enantiomers by heterocyclic decapeptides
- 论文作者：Xue Li ; Yanyan Zhu ; Wenjing Zhang ; Donghui Wei ; Mingsheng Tang
- 英文论文作者：Xue Li ; Yanyan Zhu ; Wenjing Zhang ; Donghui Wei ; Mingsheng Tang ; College of Chemistry and Molecular Engineering ; Zhengzhou University
- 年：2016
- 作者机构：College of Chemistry and Molecular Engineering, Zhengzhou University;
- 英文论文关键词：recognition ; cyclopeptide ; inclusion complexes ; enantiomers
- 会议召开时间：2016-07-01
- 会议录名称：中国化学会第30届学术年会摘要集-第十八分会：电子结构理论方法的发展与应用
- 语种：英文
- 分类号：O641
- 学会代码：ZGHY
- 会议名称：中国化学会第30届学术年会-第十八分会 ; 电子结构理论方法的发展与应用
- 会议地点：中国辽宁大连
- 主办单位：中国化学会
- 学会名称：中国化学会
- 页数：1
- 文件大小：90k
- 原文格式：D
- 会议级别：全国
摘要
Molecule recognition of chiral organic molecules by a host has become a topic of strong interest over the past decades in biomimetic organic chemistry, supramolecular chemistry, biology, and pharmacy [1,2]. Various types of hosts, such as cyclodextrins, cucurbituril, cationic pillar[n]arenes, crown ethers and calixarenes, all with the high symmetry and rigidity, present potentials of chiral recognition on organic enantiomer. However, the deficiency of conformational flexibility is a limitation regarding efficiency of inclusion complex. Recently, cyclopeptide derivatives [3,4] have attracted much attention owning to their high conformational flexibilities. In this work, the conformational and structural features of sixteen inclusion complexes of four cyclopeptides including one cyclic decapeptide(CDP) and three heterocyclic CDPs(named as I-CDP, E-CDP and H-CDP) with two enantiomers(amphetamine and ibuprofen are respectively named as AP and IP) were investigated using three density functional theories of B3LYP, CAM-B3LYP and M06-2X. The large binding energies(BE) of the five inclusion complexes, that is, the two of H-CDP/AP and H-CDP/IP by B3LYP calculation, the two of I-CDP/IP and H-CDP/IP by CAM-B3LYP, and the other one of I-CDP/IP via M06-2X method, are mainly determined by their corresponding stable geometries, electronic properties, and molecular orbitals. The existing hydrogen bonds with E(2) values and NBO analyses of the inclusion complexes further identify the relatively larger BE and △△E values. The EPS potentials and non-bonded weak interactions for the studied systems elaborated the reasons why the AP and IP enantiomers are recognized by the heterocyclic CDPs at such conformations. Possible mutants of cyclopeptides may greatly improve the corresponding molecular recognition ability on the certain enantiomers.
Molecule recognition of chiral organic molecules by a host has become a topic of strong interest over the past decades in biomimetic organic chemistry, supramolecular chemistry, biology, and pharmacy [1,2].Various types of hosts, such as cyclodextrins, cucurbituril, cationic pillar[n]arenes, crown ethers and calixarenes, all with the high symmetry and rigidity, present potentials of chiral recognition on organic enantiomer.However, the deficiency of conformational flexibility is a limitation regarding efficiency of inclusion complex.Recently, cyclopeptide derivatives [3,4] have attracted much attention owning to their high conformational flexibilities.In this work, the conformational and structural features of sixteen inclusion complexes of four cyclopeptides including one cyclic decapeptide(CDP) and three heterocyclic CDPs(named as I-CDP, E-CDP and H-CDP) with two enantiomers(amphetamine and ibuprofen are respectively named as AP and IP) were investigated using three density functional theories of B3LYP, CAM-B3LYP and M06-2X.The large binding energies(BE) of the five inclusion complexes, that is, the two of H-CDP/AP and H-CDP/IP by B3LYP calculation, the two of I-CDP/IP and H-CDP/IP by CAM-B3LYP, and the other one of I-CDP/IP via M06-2X method, are mainly determined by their corresponding stable geometries, electronic properties, and molecular orbitals.The existing hydrogen bonds with E(2) values and NBO analyses of the inclusion complexes further identify the relatively larger BE and △△E values.The EPS potentials and non-bonded weak interactions for the studied systems elaborated the reasons why the AP and IP enantiomers are recognized by the heterocyclic CDPs at such conformations.Possible mutants of cyclopeptides may greatly improve the corresponding molecular recognition ability on the certain enantiomers.
Molecule recognition of chiral organic molecules by a host has become a topic of strong interest over the past decades in biomimetic organic chemistry, supramolecular chemistry, biology, and pharmacy [1,2].Various types of hosts, such as cyclodextrins, cucurbituril, cationic pillar[n]arenes, crown ethers and calixarenes, all with the high symmetry and rigidity, present potentials of chiral recognition on organic enantiomer.However, the deficiency of conformational flexibility is a limitation regarding efficiency of inclusion complex.Recently, cyclopeptide derivatives [3,4] have attracted much attention owning to their high conformational flexibilities.In this work, the conformational and structural features of sixteen inclusion complexes of four cyclopeptides including one cyclic decapeptide(CDP) and three heterocyclic CDPs(named as I-CDP, E-CDP and H-CDP) with two enantiomers(amphetamine and ibuprofen are respectively named as AP and IP) were investigated using three density functional theories of B3LYP, CAM-B3LYP and M06-2X.The large binding energies(BE) of the five inclusion complexes, that is, the two of H-CDP/AP and H-CDP/IP by B3LYP calculation, the two of I-CDP/IP and H-CDP/IP by CAM-B3LYP, and the other one of I-CDP/IP via M06-2X method, are mainly determined by their corresponding stable geometries, electronic properties, and molecular orbitals.The existing hydrogen bonds with E(2) values and NBO analyses of the inclusion complexes further identify the relatively larger BE and △△E values.The EPS potentials and non-bonded weak interactions for the studied systems elaborated the reasons why the AP and IP enantiomers are recognized by the heterocyclic CDPs at such conformations.Possible mutants of cyclopeptides may greatly improve the corresponding molecular recognition ability on the certain enantiomers.
引文
[1]Connors,K.A.Chem.Rev.1997,97(5):1325-1358.
[2]Sun,Y.;Ma,J.;Tian,D.M.;Li,H.B.Chem.Commun.2016,52(25):4602-4612.
[3]Zhao,H.G.;Zhu,Y.Y.;Tong,M.Q.;Tang,M.S.J.Mol.Model.2011,18(3):851-858.
[4]Zhu,Y.Y.;Zhao,H.G.;Liu,C.M.;Tang,M.S.Struct.Chem.2014,25(3):699-705.
[2]Sun,Y.;Ma,J.;Tian,D.M.;Li,H.B.Chem.Commun.2016,52(25):4602-4612.
[3]Zhao,H.G.;Zhu,Y.Y.;Tong,M.Q.;Tang,M.S.J.Mol.Model.2011,18(3):851-858.
[4]Zhu,Y.Y.;Zhao,H.G.;Liu,C.M.;Tang,M.S.Struct.Chem.2014,25(3):699-705.