Design and synthesis of amphiphilic basic peptides with antibacterial activity and their interaction with model membrane.

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概要

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• Twelve peptides having 4 to 6 basic amino acid residues in the hydrophobic amino acid sequence were designed and synthesized by the solution method to find peptides with potential activity against Gram-positive and -negative bacteria. CD study of the peptides demonstrated that they formed α-helical structures in the presence of phospholipid liposomes consequently to have amphiphilic property along the axis of helix. The peptides also induced the leakage of the dye carboxyfluorescein from phospholipid vesicles, indicating that the peptides possess the ability to perturb the membrane structure. These peptides showed antibacterial activity against Gram-positive bacteria, and some of them were also active against Gram-negative bacteria. Relationships between the structure and antibacterial activity of the synthetic peptides were discussed.

• 公益社団法人 日本化学会の論文

著者

• Aoyagi Haruhiko

  Laboratory Of Biochemistry Faculty Of Science Kyushu University

• Lee Sannamu

  Laboratory Of Biochemistry Faculty Of Science Kyushu University

• Izumiya Nobuo

  Laboratory Of Biochemistry Faculty Of Engineering Kyushu Sangyo University

• KANMERA Tatsuhiko

  Laboratory of Biochemistry, Faculty of Science, Kyushu University

• KATO Tetsuo

  Laboratory of Biochemistry, Faculty of Science, Kyushu University

• MIHARA Hisakazu

  Laboratory of Biochemistry, Faculty of Science, Kyushu University

• Yoshida Mutsuo

  Laboratory of Biochemistry, Faculty of Science, Kyushu University 33

• Mihara Hisakazu

  Laboratory of Biochemistry, Faculty of Science, Kyushu University 33

• Lee Sannamu

  Laboratory of Biochemistry, Faculty of Science, Kyushu University 33

• Kato Tetsuo

  Laboratory of Biochemistry, Faculty of Science 33, Kyushu University

関連論文

• A Novel Amino Acid Derivative for Fluorescence-labeling of Carboxyl Groups in Proteins(Biological Chemistry)
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• Studies of bitter peptides from casein hydrolyzate. X. Synthesis and bitter taste of H-Arg-Gly-Pro-Phe-Pro-Ile-Ile-Val-OH corresponding to C-terminal portion of .BETA.-casein.
• Synthesis of unusual aromatic L-amino acids by asymmetric hydrogenation of cyclic dehydrodipeptides.
• Cyclic peptides. XXIII Synthesis of retro-enantio-AM-toxin I.
• Synthesis of a Lactam Analog of AM-Toxin I
• Racemization during the synthesis of histidine-containing peptides.
• Studies of Peptide Antibiotics. XVIII. The Synthesis of Tyrocidine E
• Facile synthesis of (2R,3R)-phenylalanine-2,3-d2 and NMR study on deuterated gramicidin S.
• Resolution of amino acids. XII. Preparation of L-2-amino-5-arylpentanoic acids, constituent amino acids in AM-toxins.
• Stereoselective synthesis of 2,4-diamino acids by asymmetric hydrogenation.
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• Design and synthesis of amphiphilic basic peptides with antibacterial activity and their interaction with model membrane.
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• Synthetic identification of bitter heptapeptide in tryptic hydrolysate of casein.
• Synthesis of Enantio AM-toxin I
• Resolution of .ALPHA.-formyl-.EPSILON.-acyl-DL-lysines by acylase.
• Studies of Peptide Antibiotics. XX. Synthesis of Tyrocidine B
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• Studies of Peptide Antibiotics. XVI. Analogs of Gramicidin S Containing β-Alanine in Place of L-Proline
• Studies on separation of amino acids and related compounds. VIII. Preparative separation of isomeric L-aspartyl-L-phenylalanine methyl esters and related dipeptide esters by ion-exchange chromatography.
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• Facile synthesis of cyclic dipeptides and detection of racemization.
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• Studies of Peptide Antibiotics. XXX. Syntheses of Gramicidin S Analogs Containing N-Methylleucine in Place of Leucine
• Studies of peptide antibiotics. XXXIII. Syntheses of gramicidin S analogs containing N-methyl-L-valine in place of L-valine.
• Synthesis of .ALPHA. substance-IB in Saccharomyces cerevisiae.
• Synthesis of cyclo-Diglycyl-L-tyrosyl-diglycyl-L-tyrosyl and Hydrolysis by Chymotrypsin
• Cyclic peptides. IV. Synthesis of diastereomeric dihydro-AM-toxin I and its analogs.
• Studies of peptide antibiotics. XXXIV. Syntheses of tyrocidine A and its analogs containing glycine.

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