A New Practical Strategy for the Synthesis of Long-Chain Phosphopeptide

スポンサーリンク

概要

• 論文の詳細を見る

• A new practical strategy has been developed for the synthesis of long-chain phosphopeptide. Both the 2-chlorobenzyloxycarbonyl (ClZ) group for Lys and methyl (Me) for phosphoamino acids remained intact, while other commonly used side-chain protecting groups were cleaved quantitatively, during the reaction using a highly acidic trifluoromethanesulfonic acid (TFMSA)-based reagent system (High TFMSA : TFMSA-TFA-m-cresol=1 : 9 : 1,v/v). Selective deprotection of the ClZ and Me group-containing protected phosphopeptide resin with the High TFMSA gave a partially protected phosphopeptide fragment suitable for thioester-mediated fragment condensation. A deprotection protocol of the 9-fluorenylmethyloxycarbonyl (Fmoc) group, which evades significant side reaction toward the protected phosphoamino acid, was also developed. These two new findings enabled us to synthesize long-chain phosphopeptide via thioester-mediated fragment condensation.

• 2000-08-01

著者

• Otaka Akira

  Graduate School Of Pharmaceutical Sciences Kyoto University

• Omagari Akane

  Graduate School Of Pharmaceutical Sciences Kyoto University

• Fujii N

  Graduate School Of Pharmaceutical Sciences Kyoto University

• Fujii Nobutaka

  Graduate School Of Pharmaceutical Sciences Kyoto University

• Tamamura Hirokazu

  Graduate School Of Pharmaceutical Sciences Kyoto University

• Miyoshi K

  秋田県立大学生物資源科学部

• Otaka Akira

  Univ. Tokushima Tokushima Jpn

• MIYOSHI Kengo

  Graduate School of Pharmaceutical Sciences, Kyoto University

• KANEKO Midori

  Graduate School of Pharmaceutical Sciences, Kyoto University

関連論文

• 猫乳腺腫瘍の転移におけるケモカインとケモカイン受容体の役割の検討(生化学)
• Stereodivergent Synthesis of Chiral 2-Alkenylaziridines : Palladium(0)-Catalyzed 2,3-cis-Selective Aziridination and Base-Mediated 2,3-trans-Selective Aziridination
• Synthesis of a CC Chemokine, vMIP-II, Encoded by Kaposi's Sarcoma-Associated Herpesvirus and Its Biological Activity
• Development of Chemical Probes for the Chemokine Receptor CXCR4 Involving Radiolabeled T140 Analogs
• Development of the Chemokine Receptor CXCR4 Antagonists as Multi-Pharmaceutical Agents Involving a New Class of Low Molecular Weight Antagonists
• P-423 Structure-Activity Relationship Studies on Cyclic Peptide-Based CXCR4 Antagonists
• Synthesis and Biological Evaluation of Peptidomimetic Analogs of the CXCR4 Antagonist FC131
• The Chemokine Receptor CXCR4 as a Therapeutic Target for Several Diseases Including AIDS, Cancer and Rheumatoid Arthritis
• New Leads of Low Molecular Weight CXCR4 Antagonists Based on Enhancement of the T140-based Pharmacophores
• A New Strategy for Molecular-size Reduction of Bioactive Peptide, Using Two Orthogonal Libraries of Cyclic peptides
• CXCR4 Antagonists Identified as Anti-Cancer-Metastatic Agents
• Synthesis of Novel Anti-HIV Peptides Based on a CXCR4 Antagonist, T140, and Their SAR Study
• Development of Specific CXCR4 Inhibitors Based on an Anti-HIV Peptide, T140, and Their Structure-Activity Relationships Study
• Increase of R5 HIV-1 infection and CCR5 expression in T cells treated with high concentrations of CXCR4 antagonists and SDF-1
• HIV-cell Fusion Inhibitors Targeted to the HIV Second Receptor : T22 and Its Downsized Analogs with High Activity
• Design, Synthesis and Activity of Shortened Analogs of an Anti-HIV Peptide, T22
• リン酸化ペプチドの化学合成 (構造生物学のフロンティア--シグナル伝達とDNAトランスアクション) -- (構造生物学の方法論の新しい展開)
• Helix Inducible Motifs Affect Helicity and Bioactivity of Anti-HIV Peptides
• Molecular Size of an Anti-HIV Peptide, T22, Can Be Reduced without Loss of the Activity
• STRUCTURE-ACTIVITY RELATIONSHIPS OF TACHYPLESIN ANALOGS AS ANTI-HIV AGENT
• Synthesis of CXCR4 Antagonists, T140 Derivatives with Improved Biostability, and Their SAR Study
• Development of Fusion-inhibiting Anti-HIV-1 Peptides Based on the Structure of Molecular Complex Involved in HIV-1-cell Fusion
• Synthesis and Biological Activity of Bombesin Analogues Containing (E)-Alkene Dipeptide Isosteres
• Development of Stimulus-Responsive Amino Acid with Peptide Bond-Cleavage Ability and Its Application to a Nucleocytoplasmic Shuttle Peptide
• Efficient Synthesis of Cyclic RGD Pseudopeptide with (E)-Alkene Dipeptide Isostere and Its Biological Activity
• Identification of a Polyphemusin Analog(T22)-Zn(II) Complex by Mass Spectrometric Analysis and Its Anti-HIV Activity
• Identification of Binding Proteins of an Anti-HIV Peptide, T22
• Synthesis and Application of Novel Fluorescence-Labeled CXCR4 Antagonists
• Design and Synthesis of Highly Active Anti-HIV Peptide Based on Gp41-C34 Peptide
• P-467 Structure-activity relationship study on GPR54 agonists
• Synthesis of Alkene Type Dipeptide Isosteres and Their Use to Probe the Structural Requirements of Peptide Transporter (PEPT1)
• Structure-Activity Relationship Study on hOT7T175 Agonist with RW-Amide
• Synthesis of (Z)-Alkene cis-Ala-Pro Mimetics Using Organocopper Reagents
• Endeavors for Highly Stereoselective Synthesis of Functionalized Fluoroalkene Dipeptide Isosteres
• Stereoselective Synthesis of Diketopiperazine Mimetics as Promising Scaffolds for Drug Discovery Utilizing Organocopper-Mediated anti-S_N2' Reaction
• Synthesis of ψ[(E)-CH=CMe]- and ψ[(Z)-CH=CMe]-type Dipeptide Isosteres and their Application to a Cyclic RGD Peptide
• Synthesis of ψ[(E)-CMe=CMe]- and ψ[(E)-CMe=CH]-type Alkene Dipeptide Isosteres from a Chiral Amino Acid
• Properties of Intracellular Fragment Peptides of Mouse Prostaglandin E_2 Receptor EP3 Isoform
• Inhibitory Effect of Newly Developed CXC-Chemokine Receptor 4 Antagonists on the Infection with Feline Immunodeficiency Virus(Virology)
• 難治性疾患をターゲットとしたペプチド創薬
• Antimicrobial Activity and Conformation of Tachyplesin I and Its Analogs
• Acceleration of the N^α-Deprotection Rate by the Addition of m-Cresol to Diluted Methanesulfonic Acid and Its Application to the Z(OMe)-Based Solid-Phase Syntheses of Human Pancreastatin-29 and Magainin 1
• Synthetic Studies of Tokaramide A and Miraziridine A Isolated from Marine Sponge Theonella aff. mirabilis
• A New Practical Strategy for the Synthesis of Long-Chain Phosphopeptide
• Synthesis of Nonhydrolyzable Phosphothreonine Derivatives and Their Practical Application to Peptide Synthesis
• Practical Phosphoeptides Synthesis Using Dimenthylphosphono Amino Acids (No.2)
• Specific Fluorescence Labeling of Membrane Receptors in Living Cells using Coiled-coil Tag
• Identification of Biologically Active Peptides in Laminin-1
• Fluoroalkene Skeleton as a Peptide Bond Mimetic : Its Scope and Limitations
• Establishment and Clinical Application of an Enzyme Immunoassay for Metastin to Determination of the Human Plasma Levels
• A Novel Oxazolidine Linker for the Synthesis of Peptide Aldehydes
• Structure-Activity Relationship Studies on GPR54 Agonists
• Development of Low Molecular Weight CXCR4 Antagonists by Exploratory Structural Tuning of Cyclic Tetrapeptide-scaffolds
• Biological Activity of a Cyclic Peptide from Laminin α1 Chain Loop Region
• HSP47-Binding Structural Epitopes in Triple Helical Collagen
• Synthesis of (Z)-Alkene cis-Xaa-Pro Type Dipeptide Isosteres Using Organocopper-Mediated Anti-S_N2' Reactions
• 4-(Dimethylamino)phenacyl Group : New Photoremovable Protecting Group for Amines and Carboxylic Acids
• Acid-catalyzed Ring-opening Reactions of β-Aziridinyl-α, β-enoates and Their Application
• Structure-Activity Relationship Study of CXCR4 Antagonists on the Cyclic Pentapeptide Scaffold : Identification of New Pharmacophore Moieties
• Application of Ring Closing Olefin Metathesis to the Conformational Restriction of Biologically Active Peptide. Part 1
• Identification of Novel HIV-1 Fusion Inhibitors by Template-Assisted Peptide Aldehyde Ligation
• Structure Activity Relationship Study of the Helix-inducible Motifs in HIV Fusion Inhibitors
• X-ray Crystallographic Study of the HIV-1 Fusion Inhibitor against the Drug-Resistant N43D Variant
• Bioorganic Synthesis of End-capped HIV-1 Fusion Inhibitor SC35EK
• Effect of a New Bombesin Receptor Antagonist, (E)-Alkene Bombesin Isostere, on Amylase Release from Rat Pancreatic Acini
• Stereoselective Synthesis of CF_2 or CHF-Substituted Phosphoamino Acids and Their Incorporation into Peptides
• Synthesis of β-Secretase Inhibitors Containing a Hydroxyethylamine Dipeptide Isostere and their Structure-activity Relationship Studies
• Synthesis of Peptide Thioesters using N-Substituted Aniline Derivatives
• Interactions between Local Anesthetics and Na^+ Channel Inactivation Gate Peptides in Phosphatidylserine Suspensions as Studied by ^1H-NMR Spectroscopy
• Translocation of Basic Peptides through Human Cell Membranes
• Development of Novel GPR54 Agonists with Resistance to Degradation by MMP
• Diastereoselective Synthesis of (Z)-Fluoroalkene Dipeptide Isostere and the Application to a HIV Membrane Fusion Inhibitor
• Diastereoselective Synthesis of Trifluoromethylalkene Dipeptide Isosteres Based on Nucleophilic Trifluoromethylation
• Synthesis of Peptide Thioester Based on N-S Acyl Transfer Utilizing Cysteine-derived Acyloxazolidinone with Practical Application to Peptide Synthesis
• A Highly Stereoselective Synthesis of the Functionalized (E)-Alkene Dipeptide Isostere of Trp-Val via Organocyanocopper-Lewis Acid Mediated Reaction
• A Highly Stereoselective Synthesis of The Functionalized (E)-Alkene Dipeptide Isostere of Trp-Val via Organocyanocopper-Lewis Acid Mediated Reaction
• New Strategy for The Synthesis of Aspartyl Protease Inhibitor Based on "Aza-Payne Rearrangement"
• Synthetic Studies on 7TM-GPCR (I) : Lipid Bilayer Assisted Membrane Peptide Ligation
• Utility of Plasma Bioactive Peptides Levels as Biomarkers
• Synthesis of (E)-Alkene trans-Xaa-Pro Mimetics Using Organocopper Reagents
• Stereoselective Synthesis of Peptidomimetics with Hydroxyethylamine Dipeptide Isosteres Utilizing Aza-Payne Rearrangement and O, N-Acyl Transfer Reactions
• Influence of an Amino Acid Sequence on Kinetics of Peptide Bond Cleavage Reaction Induced by a Stimulus-responsive Amino Acid
• Application of Peptide Thioacids to NCL-type Sequential Condensation of Peptide Fragments
• Development of Potent β-Secretase Inhibitors Containing a Hydroxyethylamine Dipeptide Isostere
• Stereoselective Synthesis of Tyr-Orn Type Alkene Dipeptide Isosteres and Their Application to Bioactive Peptides
• Functional Characterization of Kisspeptin Receptor Ligands : Activation of Neuropeptide FF Receptors
• Development of Stimulus Responsive Thiol Releasing System for Controlling Activity of Cysteine Protease
• P-202 DEVELOPMENT OF PHOTO-TRIGGERED SELF-PROCESSING PEPTIDES
• Development of Recapturable Cleavable Linker for Efficient Enrichment and Specific Labeling of Target Proteins
• Native Chemical Ligation Using N-peptidyl Anilide as Crypto-thioester
• Enantioselective Synthesis of Stimulus-responsive Amino Acid via Pyrrolidinyl Tetrazole Catalyzed Asymmetric α-Amination of Aldehyde
• Synthesis and Biological Evaluation of CXCL14 and Its Derivatives
• Synthesis of Fluoroalkene Dipeptide Isosteres Utilizing Organocopper or SmI_2 Reagents
• 高付加価値ペプチド合成のための最終脱保護法の開発と細胞内情報伝達機構解明への展開研究
• Synthetic Studies on Coibamide A
• High-Throughput Turbidimetric Screening for Heparin-Neutralizing Agents and Low-Molecular-Weight Heparin Mimetics
• Chronic Peripheral Administration of Kappa-Opioid Receptor Antagonist Advances Puberty Onset Associated with Acceleration of Pulsatile Luteinizing Hormone Secretion in Female Rats
• Enhanced Plasmid DNA Transfer into Tumor Cells by Nanoparticle Composed of Cholesteryl Triamine and Diamine
• Effects of Full-Length Kisspeptin Administration on Follicular Development in Japanese Black Beef Cows
• Synthesis and Investigation of Novel Metal Complexes of Deferriferrichrysin

もっと見る 閉じる

スポンサーリンク