Structural Chemistry

, Volume 28, Issue 6, pp 1631–1644 | Cite as

Molecular recognition of cyclodecapeptides to ibuprofen and naproxen enantiomers: a theoretical study

  • Xue Li
  • Yanyan Zhu
  • Chunmei Liu
  • Xincheng Lin
  • Wenjing Zhang
  • Mingsheng Tang
Original Research


Cyclopeptide derivatives have attracted great interest in host-guest chemistry during the past decades. In this work, four cyclopeptides including one cyclodecapeptide (CDP) and three modified CDPs (M-CDP involves I-CDP, E-CDP, and H-CDP) are adopted as hosts to differentiate the four guests of the amphetamine (AP) and ibuprofen (IP) enantiomers using a proposed integrated computation protocol. The obtained results demonstrated that the guests of AP and IP enantiomers could be recognized by different cyclopeptides using the certain optimized quantum chemistry methods. Specifically, the AP or IP enantiomers might be identified by the corresponding cyclopepitdes in the five pairs of the inclusion complexes associated with the large differences of binding energies of hosts with guests, that is, the two of H-CDP/AP and H-CDP/IP by B3LYP, the two of I-CDP/IP and H-CDP/IP by CAM-B3LYP, and the other one of I-CDP/IP by M06-2X, which are mainly determined by their corresponding stable conformations, electronic properties, and favorable interactions. The intermolecular hydrogen bonds and NBO analyses of the inclusion complexes further suggest the corresponding differences of binding energies. The visual nonbonded weak interactions for the studied systems gave the reasons why the AP and IP enantiomers are identified by the corresponding cyclopeptides. Molecular dynamics simulated results further support the above conclusions. The investigation provides detailed information at a molecular level about the recognition of the two chiral drug molecules by the four cyclodecapeptides. The integrated computation protocol proposed in this work provides people a feasible way to study interaction of hosts and guests, molecular recognition, and chiral separation.


Molecular recognition Cyclodecapeptide Ibuprofen Naproxen Host-guest Inclusion 



This work was financially supported by the National Natural Science Foundation of China (No. 21001095 and J1210060), University Key Research Programs of Department of Education in Henan Province (No. 15A150082 and 14A150033), and Undergraduate Innovative Training Program of Zhengzhou University (2016xjxm264).

Supplementary material

11224_2017_929_MOESM1_ESM.docx (598 kb)
Figure S1 Electrostatic potential maps for the host molecules of CDP, I-CDP, E-CDP and H-CDP calculated at the B3LYP/6–311++G(d,p) level of theory (red = less positive potential, blue = more positive potential). (DOCX 597 kb)


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Copyright information

© Springer Science+Business Media New York 2017

Authors and Affiliations

  • Xue Li
    • 1
  • Yanyan Zhu
    • 1
  • Chunmei Liu
    • 1
  • Xincheng Lin
    • 1
  • Wenjing Zhang
    • 1
  • Mingsheng Tang
    • 1
  1. 1.College of Chemistry and Molecular EngineeringZhengzhou UniversityZhengzhouPeople’s Republic of China

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