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DFT studies on inclusion complexes of 1-phenyl-1-propanol enantiomers with modified cyclic decapeptides

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Abstract

The inclusion complexes of two modified cyclic decapeptides with 1-phenyl-1-propanol (PP) enantiomers were first studied using the density functional theory B3LYP method. Our calculated results indicated that modified cyclic decapeptide (CM-CDP and DA-CDP) could form stable inclusion complexes. Significantly, based on the structural characteristics and hydrogen bond analyses, we found that the primary driving force of inclusion complex formation is a cooperative work of hydrogen bonds, steric effect, and electronic interactions, which facilitates the enhancement of binding affinity of the PP enantiomers with CM-CDP and DA-CDP. The current study shows that modified cyclic decapeptide is a desirable host molecule for chiral and molecular recognition.

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References

  1. Lehn JM (1988) Angew Chem Int Ed Engl 27:89

    Article  Google Scholar 

  2. Cram DJ (1009) Angew Chem Int Ed Engl 1988:27

    Google Scholar 

  3. Chankvetadze B, Endresz G, Blaschke G (1996) Chem Soc Rev 25:141

    Article  CAS  Google Scholar 

  4. Chankvetadze B (1997) J Chromatogr A 792:269

    Article  CAS  Google Scholar 

  5. Fanali S (2000) J Chromatogr A 875:89

    Article  CAS  Google Scholar 

  6. Armstrong DW, Nair UB (1997) Electrophoresis 18:2331

    Article  CAS  Google Scholar 

  7. Ward TJ, Oswald TM (1997) J Chromatogr A 792:309

    Article  CAS  Google Scholar 

  8. Haginaka J (2000) J Chromatogr A 875:235

    Article  CAS  Google Scholar 

  9. Otsuka K, Terabe S (2000) J Chromatogr A 875:163

    Article  CAS  Google Scholar 

  10. Kobayashi J, Tsuda M, Nakamura T, Mikami Y, Shigemori H (1993) Tetrahedron 49:2391

    Article  CAS  Google Scholar 

  11. Gulavita NK, Gunasekera SP, Pomponi SA, Robinson EV (1992) J Org Chem 57:1767

    Article  CAS  Google Scholar 

  12. Yuan LM, Fu RN, Tan NH, Ai P, Zhou J, Wu P, Zi M (2002) Anal Lett 35:203

    Article  CAS  Google Scholar 

  13. Lewis JP, Pawley NH, Sankey OF (1997) J Phys Chem B 101:10576

    Article  CAS  Google Scholar 

  14. De Lorenzi E, Massolini G, Molinari P, Galbusera C, Longhi R, Marinzi C, Consonni R, Chiari M (2001) Electrophoresis 22:1373

    Article  Google Scholar 

  15. Marinzi C, Longhi R, Chiari M, Consonni R (2001) Electrophoresis 22:3257

    Article  CAS  Google Scholar 

  16. Cao YJ, Xiao XH, Lu RH, Guo QX (2003) J Incl Phenom Mol Recognit Chem 46:195

    CAS  Google Scholar 

  17. Ranganathan D (2001) Acc Chem Res 34:919

    Article  CAS  Google Scholar 

  18. Kubik S, Bitta J, Goddard R, Kubik D, Pohl S (2001) Mater Sci Eng C 18:125

    Article  Google Scholar 

  19. Park K-H, Kurth MJ (2002) Tetrahedron 58:8629

    Article  CAS  Google Scholar 

  20. Abell AD (2002) Lett Pept Sci 8:267

    Article  CAS  Google Scholar 

  21. Hrnby VJ, Balse PM (2000) Curr Med Chem 7:945

    Article  Google Scholar 

  22. Katrin B, Lorenz UD (2003) Lett Pept Sci 10:111

    Article  Google Scholar 

  23. Garcia ME, Gavin JA, Deng N, Andrievsky AA, Mallouk TE (1996) Tetrahedron Lett 37:8313

    Article  CAS  Google Scholar 

  24. Gavin JA, Garcia ME, Benesi AJ, Mallouk TE (1998) J Org Chem 63:7663

    Article  CAS  Google Scholar 

  25. Ranganathan D, Haridas V, Karle IL (1998) J Am Chem Soc 120:2695

    Article  CAS  Google Scholar 

  26. Hu X, Chan AS, Han X, He J, Cheng JP (1999) Tetrahedron Lett 40:7115

    Article  CAS  Google Scholar 

  27. Zhao HG, Zhu YY, Tong MQ, He J, Liu CM, Tang MS (2012) J Mol Model 18:851

    Article  CAS  Google Scholar 

  28. Zhang XX, Bradshaw JS, Izatt RM (1997) Chem Rev 97:3313

    Article  CAS  Google Scholar 

  29. Kataoka H, Hanawa T, Katagi T (1992) Chem Pharm Bull 40:570

    Article  CAS  Google Scholar 

  30. Cao YJ, Xiao XH, Lu RH, Guo QX (2003) J Incl Phenom Mol Recognit Chem 46:195

    CAS  Google Scholar 

  31. Yoshida A, Arima H, Uekama K, Pitha J (1988) Int J Pharm 46:217

    Article  CAS  Google Scholar 

  32. Chen G, Su S, Liu R (2002) J Phys Chem B 106:1570

    Article  CAS  Google Scholar 

  33. Okamoto H, Nakanishi T, Nagai Y, Kasahara M, Takeda K (2003) J Am Chem Soc 125:2756

    Article  CAS  Google Scholar 

  34. Yan CL, Li XH, Xiu ZL, Hao C (2006) J Mol Struct Theochem 764:95

    Article  CAS  Google Scholar 

  35. Becke AD (1993) J Chem Phys 98:5648

    Article  CAS  Google Scholar 

  36. Lee C, Yang W, Parr RG (1988) Phys Rev B 37:785

    Article  CAS  Google Scholar 

  37. Aki H, Niiya T, Iwase Y, Kawasaki Y, Kumai K, Kimura T (2004) Thermochim Acta 416:87

    Article  CAS  Google Scholar 

  38. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr., Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2004) Gaussian 03, Revision C.01. Gaussian, Inc. Wallingford, CT

  39. Khattabi S, Cherrak DE, Mihlbachler K, Guiochon G (2000) J Chromatogr A 893:307

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The work described in this paper was supported by the National Natural Science Foundation of China (Nos. 21001095 and J1210060).

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Authors and Affiliations

  1. The College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou, 450001, Henan Province, People’s Republic of China

    Yanyan Zhu, Hongge Zhao, Chunmei Liu, Donghui Wei, Xue Li, Shijun Li & Mingsheng Tang

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  1. Yanyan Zhu
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  2. Hongge Zhao
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  3. Chunmei Liu
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  4. Donghui Wei
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  5. Xue Li
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  6. Shijun Li
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  7. Mingsheng Tang
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Correspondence to Yanyan Zhu or Donghui Wei.

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Zhu, Y., Zhao, H., Liu, C. et al. DFT studies on inclusion complexes of 1-phenyl-1-propanol enantiomers with modified cyclic decapeptides. Struct Chem 25, 699–705 (2014). https://doi.org/10.1007/s11224-013-0333-y

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  • DOI: https://doi.org/10.1007/s11224-013-0333-y

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