Synthesis and properties of a heterodetic cyclic peptide: Gramicidin S analog containing disulfide bond.
スポンサーリンク
概要
- 論文の詳細を見る
In order to investigate the relationship between the structure of a peptide backbone and the formation of an intramolecular disulfide bond (S–S) in the peptide, a linear analog (<B>1</B>) of gramicidin S and a heterodetic cyclic peptide containing an S–S bond (<B>2</B>) were synthesized by the conventional solution method. Since a disulfide bonded compound (<B>2</B>) was easily formed by a treatment of the acetamidomethyl(Acm)-protected linear peptide (<B>1</B>) with iodine in good yield (70%), it is suggested that the mutual position between Cys<SUP>1</SUP> and Cys<SUP>8</SUP> residues becomes approximate, owing to the contribution of –D-Phe–Pro– part of the sequence. A heterodetic cyclic peptide (<B>2</B>) showed about 1/16–1/8 fold activity compared to that of GS; <B>1</B> as inactive. By the construction of an S–S bridge on the peptide backbone (<B>1</B>), an inactive peptide derivative was effectively converted to an active analog (<B>2</B>). The CD spectrum pattern also suggests that the heterodetic cyclic peptide (<B>2</B>) has a GS-like structure.
- 公益社団法人 日本化学会の論文
著者
-
Okuda Hirofumi
Department Of Pediatric Cardiology The Heart Institute Of Japan Tokyo Women 's Medical College
-
Satoh Ken-ichi
Department Of Applied Physics Graduate School Of Engineering Tohoku University
-
Kodama Hiroaki
Department Of Anatomy Ohu University School Of Dentistry
-
Kondo Michio
Department Of Chemistry Faculty Of Science And Ehgineering Saga University
-
Horimoto Hideaki
Department of Chemistry, Faculty of Science and Engineering, Saga University
-
Satoh Ken-ichi
Department of Chemistry, Faculty of Science and Engineering, Saga University
-
Okuda Hirofumi
Department of Chemistry, Faculty of Science and Engineering, Saga University
関連論文
- Trans-Bilayer Ion Conduction by Proline Containing Cyclic Hexapeptides and Effects of Amino Acid Substitutions on Ion Conducting Properties
- Structure-Activity Relationship of Model Peptides Capable of Ion Channel Formation
- Hemodynamic Response to Exercise in Patients 2 to 6 Years after Rastelli Operation
- VENTRICULAR FUNCTION IN PATIENTS WITH CONGENITALLY CORRECTED TRANSPOSITION OF THE GREAT ARTERIES : Congenital Heart Disease, Kawasaki Disease : IV : 48 Annual Scientific Meeting, Japanese Circulation Society
- RIGHT VENTRICULAR FUNCTION AS A SYSTEMIC VENTRICLE : PROCEEDINGS OF THE 47th ANNUAL SCIENTIFIC MEETING OF THE JAPANESE CIRCULATION SOCIETY: Congenital Heart Disease
- Molecular evidence that most RNAs required for germination and pollen tube growth are stored in the mature pollen grain in petunia
- Modifications of Hydrophobic Value and Hydrophobic Moment Value of Cationic Model Peptides for Conversion of Peptide-Membrane Interactions
- Enhancement of Ion Channel Formation by Electrostatic Interaction Incorporated in Dimeric Helical Peptide
- Synthesis and Ion Conductance of Cervinin Peptides
- Antiadhesive Sites Present in the Fibronectin Type III-Like Repeats of Human Plasma Fibronectin(Molecular and Cell Biology)
- Comparison Study of Ion Channel Activities of Homo-Dimerized and Hetero-Dimerized Amphiphilic Helical Model Peptides
- Effect of Ring Size Alteration for Ion Channel Activities of Cyclic Peptides
- Solid-phase Synthesis of Tyrosine-containing Cyclic Peptides
- Ion-Channel Properties of Cyclic Hexapeptide cyclo(Pro-Xxx-Yyy)_2
- Synthesis and Ion-Channel Activity of Assembled Aib-Model Peptides
- Synthesis and Chemotaxis of fMLP analogs and Non-formylated peptides
- Inter-Meson Potentials in Dual Ginzburg-Landau Theory : Particles and Fields
- Effect of α,α-Dialkyl Amino Acids on the Protease Resistance of Peptides(Organic Chemistry)
- The Position of Aib Residues Defines the Antimicrobial Activity of Aib-Containing Peptides
- Synthesis and Properties of Transmembrane Domains of Uncoupling Protein, UCP-2
- Side Chain Effect on Ion Channel Characters of Aib Rich Peptides
- Pore-Forming Properties and Ion Selectivity of Amphiphilic Helical Aib-containing Model Peptides
- Interaction of Alanine-based Peptides with Fluoresceins and Their Fluorescence Quenching Behavior
- Interaction and Orientation of an α-Aminoisobutyric Acid-and Tryptophan-Containing Short Helical Peptide Pore-Former in Phospholipid Vesicles, as Revealed by Fluorescence Spectroscopy^1
- Structural Change in Elastin Model Peptides upon Interaction with Biologically Important Metal Ions
- Improvement of Fluidized State of Geldart's A-Type Particles with Smooth Surface by Ultra-Fine Powder Addition
- A Ti-plasmid-convertible λ Phage Vector System Harboring the Hygromycin B Phosphotransferase Gene
- Developmental Regulation of Genes for Microsome and Plastid ω-3 Fatty Acid Desaturases in Wheat (Triticum aestivum L.)
- cDNA Cloning of a Wounding-Inducible Gene Encoding a Plastid ω-3 Fatty Acid Desaturase from Tobacco
- Structural Profiles for Coacervation of Elastin-derived Polypeptides
- Reversible Affinity Labeling of Opioid Receptors via Disulfide Bonding: Discriminative Labeling of μ and δ Subtypes by Chemically Activated Thiol-Containing Enkephalin Analogs
- ACUTE HEMODYNAMIC EFFECTS OF DOPAMINE, DOBUTAMINE, AND ISOPROTERENOL IN CONGESTED INFANTS OR YOUNG CHILDREN WITH LARGE VENTRICULAR SEPTAL DEFECT
- BMP-2-Producing L cells induce osteogenesis in vivo and in vitro
- Synthesis and Properties of TN III Peptide Analogs Derived from Type III Repeat of Tenascin C
- Conformational Studies of Cyclo(Pro-Leu-Aib)_2 by ^1H Nuclear Magnetic Resonance Spectroscopy and Circular Dichroism^1
- Synthesis and Solution Conformations of Cyclo(Pro-Leu-Gly)_2 and Cyclo(Pro-Leu-Gly)_4
- Synthesis and Conformational Studies of Cyclic Peptides Containing the C-terminal Tripeptide Sequence of Oxytocin
- Elastin-derived Peptides : Structure, Functions and Mechanisms
- Molecular Mechanism for Pore-formation in Lipid Membranes by the Hemolytic Lectin CEL-III from Marine Invertebrate Cucumaria echinata
- Structure-Activity Relationship of Designed Ion-Channel Peptides
- Studies of the Plant Cell Cycle in Synchronous Cultures of Catharanthus roseus Cells : GROWTH AND DEVELTOPMENT
- アントシアニン合成およびクロロフィル分解を誘導しているトレニア再生シュートで発現する遺伝子のサプレッション サブトラクティブ ハイブリダイゼーション法とcDNAアレイ法,RNAi法を用いた解析
- Synthesis and Biological Activity of Synthetic Peptide MMK-1 Analogs
- Synthesis and Biological Activity of Non-Formyl Chemotactic Peptide Analogs as a Tool for Neutrophil Formyl Peptide Receptor Interaction
- Synthesis of FPR-Derived Transmembrane Peptides Containing Photoaffinity Amino Acid
- Superoxide Production in Human Neutrophils Is Enhanced by Treatment with Transmembrane Peptides Derived from Human Formyl Peptide Receptor
- Signal Transduction of Chemotactic Non-Formyl Peptide and Selective for Formyl Peptide Receptor
- Synthesis of Transmembrane Peptides Derived from Human Formyl Peptide Receptor and Influence on Biological Activities of Human Neutrophils
- L-5, 5-Difluoronorleucine as an Oxidation-Resistant Methionine Mimic : Facile Synthesis and its Application on Chemotactic Peptide, fMLP
- Synthesis and Biological Activity of Urease-related Peptides Generated from Helicobacter Pylori
- Interacions of Amphiphilic Aib-containing Helical Peptides with Phospholipid Membrane
- Synthesis and Secondary Structures of Aib Peptides Containing Tryptophan Residues
- Ion Channel Formation and Sequence Dependence of Aib-containing Peptides
- Purification and Characterization of the Antioxidative Substance Produced by Aspergillus sojae K
- The Recovery of Affinity-labeled Opioid Receptors to Their Intact Forms
- Photoaffinity Labeling of Formylpeptide Receptors by fMLP Analogs
- Synthesis and Neutrophil Activation of fMLP Analogs Containing Conformationally Constrained Tic Residues
- N-Phosphoarginine phosphatase (17kDa) and Alkaline Phosphatase as Protein Arginine Phosphatases
- Molecular Cloning of a cDNA that Encodes a Spinach Cysteine Synthase-Like Protein
- Synthesis of a Fluoroalkene Isoster of Acetyllysine
- Light Actions in the Germination of Cocklebur Seeds II. Possible Origin of the Diversity of Light Responses in Seed Germination
- Synthesis and Biological Activity of Dimeric Chemotactic Peptide Antagonist
- Insight into Methionine Side-Chain Recognition by the FPR Utilizing Sulfur Mimetics
- Synthesis and Biological Activity of Alamethicin Analogs Enhanced by Electrostatic Interaction
- Synthesis and Priming Activities of Cyclic Peptides, Hymenamides
- ACTIVATION OF HUMAN NEUTROPHILS BY fMLP ANALOGS CONTAINING 2,3-CYCLOPROPANE AMINO ACID
- Dimeric Chemotactic Peptides Discriminate between Chemotaxis and Superoxide Production of Human Neutrophils
- Solid-phase Synthesis and Chain-length Dependence of The Secondary Structure of α-Helical Model Peptides Containing Aib Residues
- A Tetrameric Enkephalin Analog for the Putative Multivalent Interaction with Opioid Receptors
- Contribution of hydrophobic side-chain in cyclic tetrapeptide forming ion channel
- Molecular Weight Determination of Synthetic Sequential Polypeptides in SDS-PAGE : Gel Staining Method Using Metal Chlorides
- Coacervation and Self-Assembly of Polypeptide Derived from Elastin : Effects of Metal Cations
- The elucidation of the conformational requirements for methionine side-chain interaction with FPR by using fluorinated fMLP analogs
- Structural modification of 2-aminoisobutylic acid containing peptides toward an acquiring of antimicrobial activities against pathogenic bacteria
- Synthesis of 3-Substituted 2,3-Dehydroprolines: Oxidative Decarboxylation of Ethy Hydrogen Acetoamidomalonate Derivatives
- New Cysteine Fluorometric Determination for Vegetables and Fruits Based on a Reaction with 2,6-Dichloro-p-benzoquinone and Using Thin-layer Densitometry
- Elastin Peptide Coacervate as a Model of Extracellular Elastomeric Matrix : Ionic Transport Study
- Biological Self-Assembly Model of Elastomeric Protein : Characteristics of Critical Processes in Coacervation of Elastin Peptides
- Design and Synthesis of Highly Specific and Selective Enkephalin Analog Containing S-Npys-Cysteine for δ Opioid Receptors
- Thiol-containing Enkephalins for Exploration of the Essential Thiol Group in Opiate Receptors
- Molecular evidence that most RNAs required for germination and pollen tube growth are stored in the mature pollen grain in petunia
- Fabrication of Epitaxial Silicon Thin Films for Solar Cells by Low-Temperature Reactive Thermal Chemical Vapor Deposition Technique
- Microcrystalline Silicon Solar Cells Fabricated using Array-Antenna-Type Very High Frequency Plasma-Enhanced Chemical Vapor Deposition System
- Synthesis and properties of a heterodetic cyclic peptide: Gramicidin S analog containing disulfide bond.
- Syntheses and properties of [1,1'-bis(.ALPHA.-aminoisobutyric acid)]gramicidin S and [1-.ALPHA.-aminoisobutyric acid]semigramicidin S.
- Studies of Peptide Antibiotics. XIX. Syntheses of 1,1′-Leucine-gramicidin S and 1-Leucine-cyclosemigramicidin S
- Structure-Activity Relationship of a Transmembrane Peptide Derived form Formyl Peptide Receptor 1
- Ion Channel Formation by Charged Cyclic Pentapeptides
- Interaction and Orientation of an .ALPHA.-Aminoisobutyric Acid- and Tryptophan-Containing Short Helical Peptide Pore-Former in Phospholipid Vesicles, as Revealed by Fluorescence Spectroscopy.