Synthesis, Conformation, and Chemical Properties of New Mini Parallel Double-Stranded Peptides Conjugated with -Phe-Phe- and -Phe-Phe-X- Sequences

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概要

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• To investigate the chemical conformations and functions of the -Phe-Phe-Val- or -Phe-Phe- sequences contained in the Alzheimer's disease related β-amyloid peptide, a series of mini parallel double-stranded peptides conjugated with two peptide residues to one spacer were designed and prepared. The structure of the compounds was elucidated by circular dichroism (CD) spectrum and NMR two dimensional (2D) nuclear Overhauser enhancement and exchange spectroscopy (NOESY) measurments. The structure of 1,2-ethano-bis(L-Phe-L-Phe-L-Leu), 1,12-dodecano-bis(L-Phe-L-Phe-L-Leu), 1,12-dodecano-bis(L-Phe-L-Phe-L-Val), and 1,12-dodecano (D-Phe-D-Phe-D-Leu) conjugated with L-Leu and L-Val residues show a β-turn-like nucleation. The dihedral angles (θ=+75°, +180°, ω=+90°, φ=-87°, ψ=+180°) obtained from experimental coupling constant (J) data, etc. support that 1,12-dodecano-bis(L-Phe-L-Phe) adopts β-turn mimic nucleation. The 1,12-dodecano-bis(L-Leu-L-Leu-L-Phe), 1,12-dodecano-bis(L-Ile-L-Phe-L-Leu), and 1,12-dodecano-bis(L-Phe-L-Val-L-Leu), etc. adopt most probably a random structure by CD studies.It was found by titration spectrum that an inclusion complex of 1 : 1 ratio (association constant;K_a=1.0×10^4M^<-1>) is formed between 1,12-dodecano-bis(L-Phe-L-Phe-L-Leu) and azobenzene (guest, [L_0]=1.758×10^<-5>M^<-1>). Moreover, the stability of the complexes was increased in order of 1,12-dodecano-bis(L-Phe-L-Phe-L-Leu)・azobenzene>1,12-dodecano-bis(L-Phe-L-Phe-L-Val)・azobenzene>1,12-dodecano-bis(L-Phe-L-Val-L-Leu)・azobenzene. The data show that X-Phe-L-Phe-L-spacer(S)-L-Phe-L-Phe-X (X=amino acids;S=1,2-ethano- and 1,12-dodecano-) plays an important role as a binding site of the artificial receptor. The hydrophobic interaction of the four Phes in the two strands is a very interesting issue in the physiological action of proteins as well as the conformation of the backbone of X-L-Phe-L-Phe-spacer(S)-L-Phe-L-Phe-X.

• 公益社団法人日本薬学会の論文
• 2000-07-01

著者

• 西田 昌代

  Meiji College of Pharmacy

• 宮田 直樹

  名古屋市立大学

• MIYATA Naoki

  Division of Organic Chemistry, National Institute of Health Sciences

• Kobayashi Shigeki

  Department of Medicine and Clinical Science, Yamaguchi University Graduate School of Medicine

• YAMAGUCHI KENTARO

  Chemical Analytical Center, Chiba University

• Nishida Makiko

  崇城大学 薬学部薬学科

• Yamaguchi K

  Analysis Center Chiba University

• Kobayashi Hisayoshi

  Institute Of Molecular And Cellular Biosciences The University Of Tokyo

• Tanaka Akira

  Department of Health and Nutrition, College of Human and Environmental Studies, Kanto-Gakuin Univers

• Komatsu H

  School Of Agriculture Kyushu Tokai University

• KURIHARA Masaaki

  Division of Organic Chemistry, National Institute of Health Sciences

• Miyata Naoki

  Division Of Organic Chemistry National Institute Of Health Sciences

• Tanaka A

  Faculty Of Pharmaceutical Sciences Tokyo University Of Science

• Komatsu H

  Kyoto Pharmaceutical University

• Kobayashi S

  Eisai Research Institute Of Boston Inc.

• Kobayashi Shoichi

  Laboratory Of Food And Health Science Department Of Agro-bioscience Faculty Of Agriculture Iwate Uni

• Kobayashi Hiroki

  Department Of Analytical Chemistry Of Medicines Showa Phamaceutical University

• Yamaguchi Kentaro

  Chemical Analysis Center Chiba University

• Kobayashi Shigeki

  Department Of Analytical Chemistry Of Medicines Showa Phamaceutical University

• Yamaguchi T

  Tsumura Res. Laboratories Tsumura & Co.

• Kobayashi Shigeki

  Department Of Analytical Chemistry Of Medicines Showa Pharmaceutical University

• YAMAGUCHI Takatoshi

  Department of Analytical Chemistry of Medicines, Showa Pharmaceutical University

• NISHIDA Miharu

  Department of Analytical Chemistry of Medicines, Showa Pharmaceutical University

• Kobayashi H

  Institute Of Molecular And Cellular Biosciences The University Of Tokyo

• Kobayashi Shigeki

  Div. Of Analytical Chemistry Of Medicines Showa Pharmaceutical Univ.

• Nishida Miharu

  Department Of Analytical Chemistry Of Medicines Showa Pharmaceutical University

• Kurihara M

  Division Of Organic Chemistry National Institute Of Health Sciences

• Kurihara Masaaki

  Division Of Organic Chemistry National Institute Of Health Sciences

• Yamaguchi Takatoshi

  Department Of Analytical Chemistry Of Medicines Showa Pharmaceutical University

• Miyata Naoki

  Division Of Organic Chemistry

• Yamaguchi Kentaro

  Chemical Analysis Center Chiba Univ. Chiba 263-8522 Jpn

• Tanaka Akira

  Department Of Diagnostic Pathology Jichi Medical University

• TANAKA Akira

  Department of Agricultural Chemistry, Faculty of Agriculture, Tohoku University

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