NMR Studies on Turn Mimetic Analogs Derived from Melanocyte-stimulating Hormones

Min Kyu Cho, Sung Soo Kim, Myung Ryul Lee, Joon Shin, Jiyong Lee, Sung Kil Lim, Ja Hyun Baik, Chang Ju Yoon, Injae Shin, Weontae Lee

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Oligomers with α-aminooxy acids are reported to form very stable turn and helix structures, and they are supposed to be useful peptidomimetics for drug design. A recent report suggested that homochiral oxa-peptides form a strong eight-member-ring structure by a hydrogen bond between adjacent aminooxy-acid residues in a CDCl3 solution. In order to design an α-MSH analog with a stable turn conformation, we synthesized four tetramers and one pentamer, based on α-MSH sequence, and determined the solution structures of the molecules by two-dimensional NMR spectroscopy and simulated annealing calculations. The solution conformations of the three peptidomimetic molecules (TLV, TDV, and TLL) in DMSO-d6 contain a stable 7-membered-ring structure that is similar to a γ-turn in normal peptides. Newly-designed tetramer TDF and pentamer PDF have a ball-type rigid structure that is induced by strong hydrogen bonds between adjacent amide protons and carbonyl oxygens. In conclusion, the aminooxy acids, easily prepared from natural or unnatural amino acids, can be employed to prepare peptidomimetic analogues with well-defined turn structures for pharmaceutical interest.

Original languageEnglish
Pages (from-to)552-557
Number of pages6
JournalJournal of Biochemistry and Molecular Biology
Volume36
Issue number6
Publication statusPublished - 2003 Nov 30
Externally publishedYes

Keywords

  • NMR
  • Peptidomimetics
  • Turn conformation
  • α-Aminooxy acids
  • γ-MSH

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology

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  • Cite this

    Cho, M. K., Kim, S. S., Lee, M. R., Shin, J., Lee, J., Lim, S. K., Baik, J. H., Yoon, C. J., Shin, I., & Lee, W. (2003). NMR Studies on Turn Mimetic Analogs Derived from Melanocyte-stimulating Hormones. Journal of Biochemistry and Molecular Biology, 36(6), 552-557.