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

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

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Peptidomimetics
Melanocyte-Stimulating Hormones
Nuclear magnetic resonance
Acids
Conformations
Hydrogen
Hydrogen bonds
Rigid structures
Peptides
Molecules
Drug Design
Dimethyl Sulfoxide
Simulated annealing
Oligomers
Amides
Pharmaceutical Preparations
Nuclear magnetic resonance spectroscopy
Protons
Magnetic Resonance Spectroscopy
Oxygen

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Biology

Cite this

Cho, Min Kyu ; Kim, Sung Soo ; Lee, Myung Ryul ; Shin, Joon ; Lee, Jiyong ; Lim, Sungkil ; Baik, Ja Hyun ; Yoon, Chang Ju ; Shin, Injae ; Lee, Weon Tae. / NMR Studies on Turn Mimetic Analogs Derived from Melanocyte-stimulating Hormones. In: Journal of Biochemistry and Molecular Biology. 2003 ; Vol. 36, No. 6. pp. 552-557.
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Cho, MK, Kim, SS, Lee, MR, Shin, J, Lee, J, Lim, S, Baik, JH, Yoon, CJ, Shin, I & Lee, WT 2003, 'NMR Studies on Turn Mimetic Analogs Derived from Melanocyte-stimulating Hormones', Journal of Biochemistry and Molecular Biology, vol. 36, no. 6, pp. 552-557.

NMR Studies on Turn Mimetic Analogs Derived from Melanocyte-stimulating Hormones. / Cho, Min Kyu; Kim, Sung Soo; Lee, Myung Ryul; Shin, Joon; Lee, Jiyong; Lim, Sungkil; Baik, Ja Hyun; Yoon, Chang Ju; Shin, Injae; Lee, Weon Tae.

In: Journal of Biochemistry and Molecular Biology, Vol. 36, No. 6, 30.11.2003, p. 552-557.

Research output: Contribution to journalArticle

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T1 - NMR Studies on Turn Mimetic Analogs Derived from Melanocyte-stimulating Hormones

AU - Cho, Min Kyu

AU - Kim, Sung Soo

AU - Lee, Myung Ryul

AU - Shin, Joon

AU - Lee, Jiyong

AU - Lim, Sungkil

AU - Baik, Ja Hyun

AU - Yoon, Chang Ju

AU - Shin, Injae

AU - Lee, Weon Tae

PY - 2003/11/30

Y1 - 2003/11/30

N2 - 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.

AB - 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.

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