Cyclization of several linear penta- and heptapeptides with different metal ions studied by CD spectroscopy†

  1. M. Liu,
  2. Y.-C. Tang,
  3. K.-Q Fan,
  4. X. Jiang,
  5. L.-H Lai,
  6. Y.-H Ye

Article first published online: 22 DEC 2004

DOI: 10.1111/j.1399-3011.2004.00199.x

Issue

The Journal of Peptide Research

The Journal of Peptide Research

Volume 65, Issue 1, pages 55–64, January 2005

Additional Information

How to Cite

Liu, M., Tang, Y.-C., Fan, K.-Q., Jiang, X., Lai, L.-H. and Ye, Y.-H. (2005), Cyclization of several linear penta- and heptapeptides with different metal ions studied by CD spectroscopy. The Journal of Peptide Research, 65: 55–64. doi: 10.1111/j.1399-3011.2004.00199.x

Author Information

  1. M. Liu, Y.-C. Tang and Y.-H.Ye Key Laboratory of Bioorganic Chemistry and Molecular Engineering, Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing, China K.-Q. Fan and L.-H. Lai, State Key Laboratory for Structural Chemistry Studies of Stable and Unstable Species, Institute of Physical Chemistry, College of Chemistry and Molecular Engineering, Peking University, Beijing, China X. Jiang, Accelrys, San Diego, CA, USA

*Prof. Yun-hua Ye College of Chemistry and Molecular Engineering Peking University, Beijing 100871 China E-mail: yhye@pku.edu.cn

  • †

    This paper is dedicated to the memory of Dr. Murray Goodman, an outstanding and enthusiastic scientist, professional colleague, and friend.

Publication History

  1. Issue published online: 5 DEC 2008
  2. Article first published online: 22 DEC 2004
  3. Dates: Received 29 September 2004 Accepted 31 October 2004

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Keywords:

  • CD spectra;
  • cyclic peptide;
  • cyclization;
  • DEPBT;
  • linear peptide;
  • metal ions

Abstract:  A cyclic pentapeptide c(Tyr-Leu-Ala-Gly-Pro) (I), which was isolated and identified from Pseudostellaria heterophylla medicinal herbs, and two cyclic heptapeptides, c(Gly-Tyr-Gly-Gly-Pro-Phe-Pro) (II) and c(Gly-Ile-Pro-Tyr-Ile-Ala-Ala) (III), which were isolated and identified from Stellaria yunnanensis Franch (M), were synthesized by using 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3 H)-one (DEPBT) as a coupling reagent in solution, and mediated by different metal ions, from their linear peptide precursors H-Tyr-Leu-Ala-Gly-Pro-OH (I-1) and H-Ala-Gly-Pro-Tyr-Leu-OH (I-2), H-Gly-Tyr-Gly-Gly-Pro-Phe-Pro-OH (II-1) and H-Gly-Ile-Pro-Tyr-Ile-Ala-Ala-OH (III-1), respectively. The results show that alkali metal ions can improve the cyclization yields and/or the cyclization rates of linear peptide precursors, such as Na+ ion is favorable for the cyclization of linear pentapeptides and Cs+ ion is favorable for the cyclization of linear heptapeptides, while some bivalent and trivalent metal ions, such as Mg2+, Ca2+, Zn2+, Fe2+, Ni2+ and Cr3+ reduced/inhibited both the cyclization yields and the cyclization rates of the linear peptide precursors. The circular dichroism spectra of I-1, II-1 and III-1 with different metal ions were studied to elucidate the changes in their secondary structures. It is shown that Cs+ can induce and stabilize the type I β-turn conformation in the linear heptapeptide II-1 and the type II β-turn conformation in the linear heptapeptide III-1.

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