Solution-Phase Synthesis of an Anti-human Immunodeficiency Virus Peptide, T22 ([Tyr^<5,12>, Lys^7]-Polyphemusin II), and the Modification of Trp by the p-Methoxybenzyl Group of Cys during Trimethylsilyl Trifluoromethanesulfonate Deprotection
スポンサーリンク
概要
- 論文の詳細を見る
T22 ([Tyr^<5,12>, Lys^7]-polyphemusin II) was previously synthesized by a solid-phase method and was found to have a strong anti-human immunodeficiency virus (HIV) activity, comparable to that of 3'-azido-2', 3'-dideoxy-thymidine (AZT). In the present study, the solution-phase synthesis of T22 was attempted in order to produce this peptide on a large scale. An 18-residue peptide amide corresponding to the entire amino acid sequence of T22 was synthesized by assembling four peptide fragments and two amino acid derivatives, followed by thioanisole-mediated deprotection with 1 M trimethylsilyl trifluoromethanesulfonate (TMSOTf) in trifluoroacetic acid followed by air-oxidation. During this deprotection, a significant by-product derived from the transfer of the p-methoxybenzyl (MBzl) group from the sulfhydryl group of the cysteine residue to the side chain of the tryptophan residue was formed. This side reaction was found to be efficiently suppressed by adopting a two-step deprotection procedure using silver trifluoromethanesulfonate (AgOTf)-TMSOTf or trimethylsilyl bromide (TMSBr)-TMSOTf.
- 社団法人日本薬学会の論文
- 1995-01-15
著者
-
山本 直樹
感染研
-
井深 俊郎
Faculty of Pharmaceutical Sciences, Kyoto University
-
中島 秀喜
Department Of Microbiology Yamanashi Medical University
-
玉村 啓和
Faculty of Pharmaceutical Sciences, Kyoto University
-
大高 章
Faculty of Pharmaceutical Sciences, Kyoto University
-
高田 渉
Faculty of Pharmaceutical Sciences, Kyoto University
-
寺川 良司博
Faculty of Pharmaceutical Sciences, Kyoto University
-
吉澤 秀則
Faculty of Pharmaceutical Sciences, Kyoto University
-
増田 正雄
Faculty of Pharmaceutical Sciences, Kyoto University
-
村上 努
Department of Microbiology, Tokyo Medical and Dental University, School of Medicine
-
脇 道典
SEIKAGAKU Corporation
-
松本 章義
SEIKAGAKU Corporation
-
山本 直樹
Department of Microbiology, Tokyo Medical and Dental University, School of Medicine
-
藤井 信孝
Faculty of Pharmaceutical Sciences, Kyoto University
-
玉村 啓和
東医歯大生材工研
-
玉村 啓和
東京医歯大・生材研
-
大高 章
徳島大学大学院ヘルスバイオサイエンス研究部
-
大高 章
京都大学 薬
-
藤井 信孝
京都大学大学院薬学研究科 医薬創成情報科学専攻
-
WAKI Michinori
SEIKAGAKU Corp.
-
大高 章
京大 大学院薬学研究科
-
増田 正雄
Faculty Of Pharmaceutical Sciences Kyoto University
-
井深 俊郎
Faculty Of Pharmaceutical Sciences Kyoto University
-
Nakashima H
Department Of Microbiology Yamanashi Medical University
-
Tamamura Hirokazu
Faculty Of Pharmaceutical Sciences Kyoto University
-
Tamamura Hirokazu
Dept. Of Molecular Recognition Inst. Of Biomaterials And Bioengineering Tokyo Medical And Dental Uni
-
Murakami T
Department Of Microbiology Tokyo Medical And Dental University School Of Medicine
-
高田 渉
Faculty Of Pharmaceutical Sciences Kyoto University
-
Tamamura H
Faculty Of Pharmaceutical Sciences Kyoto University
-
Nakashima H
Faculty Of Pharmaceutical Sciences Nagoya City University
-
Yoshizawa H
Faculty Of Pharmaceutical Sciences Kyoto University
-
吉澤 秀則
Faculty Of Pharmaceutical Sciences Kyoto University
-
脇 道典
Seikagaku Corp.
-
Tamamura H
Graduate School Of Pharmaceutical Sciences Kyoto University
-
寺川 良司博
Faculty Of Pharmaceutical Sciences Kyoto University
関連論文
- Studies on Morphine Alkaloids. III. Indolinocodeine. II. 9α-Methoxyindolinocodeine
- Solution-Phase Synthesis of an Anti-human Immunodeficiency Virus Peptide, T22 ([Tyr^, Lys^7]-Polyphemusin II), and the Modification of Trp by the p-Methoxybenzyl Group of Cys during Trimethylsilyl Trifluoromethanesulfonate Deprotection
- Molecular Parameters for the Anti-Human Immunodeficiency Virus Activity of T22 ([Tyr^, Lys^7]-Polyphemusin II)
- これからの抗エイズ薬 (エイズと小児科臨床)
- LIGNIFIED MATERIALS AS MEDICINAL RESOURCES. VI. ANTI-HIV ACTIVITY OF DEHYDROGENATION POLYMER OF p-COUMARIC ACID, A SYNTHETIC LIGNIN, IN A QUASI-IN-VIVO ASSAY SYSTEM AS AN INTERMEDIARY STEP TO CLINICAL TRIALS
- 抗HIV薬としてのアンチセンスDNA
- 66 ツバキおよび近縁植物の抗HIV作用を有するタンニン(ポスター発表の部)
- Lignified Materials as Medicinal Resources. V. Anti-HIV (Human Immunodeficiency Virus) Activity of Some Synthetic Lignins)
- New Substances against Human Immunodeficienty Virus : Sulfated 5'-Nucleotidase Inhibitory Polyphenols
- 感染症--新しい視点から--微生物感染症の分子病理学-1-宿主の過剰応答によりひき起こされる感染症--HIV感染症における宿主因子による病態の増悪と防御について
- どんな候補薬が開発されているか,また有望か (エイズ最前線) -- (ここまで進んだエイズ治療薬)
- 抗エイズ薬開発のストラテジ- (エイズ最前線) -- (ここまで進んだエイズ治療薬)
- Antiviral Activities of Glycyrrhizin and Its Modified Compounds against Human Immunodeficiency Virus Type 1 (HIV-1) and Herpes Simplex Virus Type 1 (HSV-1) in Vitro
- 2P055 ドッキングシミュレーションによるHIV-1インテグラーゼ阻害活性を有するペプチドの分子設計(蛋白質(構造・構造機能相関),ポスター発表,第45回日本生物物理学会年会)
- New Substances against Human Immunodeficienty Virus : Sulfated 5'-Nucleotidase Inhibitory Polyphenols
- New Substances against Human Immunodeficienty Virus : Sulfated 5'-Nucleotidase Inhibitory Polyphenols
- New Substances against Human Immunodeficienty Virus : Sulfated 5'-Nucleotidase Inhibitory Polyphenols
- New Substances against Human Immunodeficienty Virus : Sulfated 5'-Nucleotidase Inhibitory Polyphenols
- SARS治療薬の展望 (特集 ウイルス感染症--基礎と臨床) -- (基礎)
- 新しい抗HIV薬剤の開発--HIVのコレセプタ-(セカンドレセプタ-)に作用する薬剤
- HIV-1のセカンドレセプタ-の発見とその意義
- ヒトCD4発現マウスT細胞株EL-4へのHIV-1感染
- Synthesis of Protegrin-Related Peptides and Their Antibacterial and Anti-human Immunodeficiency Virus Activity
- New Substances against Human Immunodeficienty Virus : Sulfated 5'-Nucleotidase Inhibitory Polyphenols
- New Substances against Human Immunodeficienty Virus : Sulfated 5'-Nucleotidase Inhibitory Polyphenols
- Studies on Peptides. CXXXVI. : Solution-Phase Synthesis of a 37-Residue Peptide Amide Corresponding to the Entire Amino Acid Sequence of Human Calcitonin Gene-Related Peptide (hCGRP)
- Studies on Peptides. LXXVI. Synthesis of Kassinin, a New Frog Skin Peptide
- Studies on Peptides. LXXIII. Examination of the Methanesulphonic Acid Procedure for the Synthesis of Peptides containing Methionine
- Studies on Peptides. LXIX. Selective Removal of Acid Labile α-Amino Protecting Groups with Dilute Sulfonic Acids
- Studies on Peptides. XLVIII. Application of the Trifluoromethanesulphonic Acid Procedure to the Synthesis of Tuftsin
- Studies on Peptides. CXLI. : Synthesis of a 42-Residue Peptide Corresponding to the Entire Amino Acid Sequence of Porcine GIP (Glucose-Dependent Insulinotropic Polypeptide)
- Studies on Peptides. CXXXIX. : Solution Synthesis of a 42-Residue Peptide Corresponding to the Entire Amino Acid Sequence of Human Glucose-Dependent Insulinotropic Polypeptide (GIP)
- Studies on Peptides. CXXXIII. : Synthesis and Biological Activity of Galanin, a Novel Porcine Intestinal Polypeptide
- Studies on Peptides. CXXXI. Synthesis of Adrenorphin and Enkephalin Analogs
- Studies on Peptides. CXXXIV. : Evaluation of S-1-Adamantylcysteine for Peptide Synthesis
- 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
- Enzyme Immunoassay of Somatostatin (SS)-like Immunoreactive Substance in Bovine Milk
- Studies on Peptides. CLVI. Synthesis of Second Human Calcitonin Gene-Related Peptide (β-hCGRP) by Application of a New Disulfide-Bonding Reaction with Thallium(III) Trifluoroacetate(Organic,Chemical)
- Studies on Peptides. CXLII. : Synthesis of Des-1-Ala-des-α-amino-Human Calcitonin Gene-Related Peptide
- Synthesis of Optically Pure 2-Aziridinemethanols : Versatile Synthetic Building Blocks
- Studies on Peptides. CXLVI. : Synthesis of Gln^-Motilin and Examination of Its Immunological Properites
- Studies on Peptides. CXXX. Convenient Procedure for the Reduction of Methionine Sulfoxide
- Molecular Size of an Anti-HIV Peptide, T22, Can Be Reduced without Loss of the Activity
- Studies on Peptides. CLI. Syntheses of Cystine-Peptides by Oxidation of S-Protected Cysteine-Peptides with Thallium(III) Trifluoroacetate(Organic,Chemical)
- Studies on Peptides. CXLIII. : Evaluation of β-Methylaspartate for Peptide Synthesis
- A Stereoselective Synthesis of dl-Pumiliotoxin C
- exo-Adduct Predominance in the Diels-Alder Reaction of Novel 1,3-Bis-(trimethylsiloxy) cyclohexa-1,3-dienes with Acrylonitrile
- Synthesis of a Heptacosapeptide Amide corresponding to the Entire Amino Acid Sequence of Chicken Gastrin Releasing Peptide (GRP)
- Synthesis of a Heptacosapeptide Amide corresponding to the Entire Amino Acid Sequence of Gastric Gastrin Releasing Peptide
- Studies on the Alkaloids of Menispermaceous Plants. CCXX. Mass Spectra of Benzylisoquinoline Alkaloids
- Selective Transport of the Salts of Amino Acid Esters through an Organic Liquid Membrane with Antamanide as a Carrier
- Studies on Peptides. CXLVIII. : Application of a New Deprotecting Procedure with Trimethylsilyl Trifluoromethanesulfonate for the Syntheses of Two Porcine Spinal Cord Peptides, Neuromedin U-8 and Neuromedin U-25(Amaryllidaceae)(Organic,Chemical)
- 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
- Studies on Peptides. CLXVI. : Solid-Phase Syntheses and Immunological Properties of Fragment Peptides Related to Human Hepatitis B Virus Surface Antigen (HBsAg) and Its Pre-S2 Gene
- Studies on Peptides. CLVII. : Synthesis of a Frog-Skin Peptide, Sauvagine
- Studies on Peptides. CXXXII. : Evaluation of Two β-Carboxyl Protecting Groups of Aspartic Acid, Cycloheptyl and Cyclooctyl, for Peptide Synthesis
- Studies on Peptides. CXXXV. : Preparation of Seven Peptide Fragments for the Synthesis of Human Calcitonin Gene-Related Peptide (hCGRP)
- Studies on Peptides. CXXIV. Solution Synthesis of the Hentetracontapeptide Amide Corresponding to the Entire Amino Acid Sequence of Human Corticotropin Releasing Factor (hCRF)
- Studies on Peptides. CXXIII. Preparations of Nine Peptide Fragments for the Synthesis of Human Corticotropin Releasing Factor (hCRF)
- SYNTHESIS OF A HENTETRACONTAPEPTIDE AMIDE CORRESPONDING TO THE ENTIRE AMINO ACID SEQUENCE OF HUMAN CORTICOTROPIN RELEASING FACTOR (hCRF)
- Studies on Peptides. CXVII. Solution Synthesis of the Tetratetracontapeptide Amide Corresponding to the Entire Amino Acid Sequence of Growth Hormone Releasing Factor, Somatocrinin
- SOLUTION SYNTHESIS OF A TETRATETRACONTAPEPTIDE AMIDE WITH GROWTH HORMONE RELEASING ACTIVITY
- Total Synthesis of the Alkaloid (±)-Dendrobine
- Studies on Peptides. CXXXVIII. : Conventional Solution Synthesis of Bovine Hypothalamic Growth Hormone Releasing Factor (bGRF)
- Studies on Peptides. CXXXVII. : Conventional Solution Synthesis of Porcine Hypothalamic Growth Hormone Releasing Factor (pGRF)
- STEPHADIAMINE, A NEW SKELETAL ALKALOID FROM STEPHANIA JAPONICA : THE FIRST EXAMPLE OF A C-NORHASUBANAN ALKALOID
- 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
- Immuno-affinity Purification of Specific Antibodies against Vasoactive Intestinal Polypeptide (VIP) on VIP (1-10)-Linked Polydimethylacrylamide Resin
- S-BENZYLOXYMETHYLCYSTEINE, ITS PROPERTIES AND APPLICATION IN THE SYNTHESIS OF PORCINE BRAIN NATRIURETIC PEPTIDE (pBNP)
- Studies on Peptides. CLXII. : Synthesis of Chicken Calcitonin-Gene-Related Peptide (cCGRP) by Application of Sulfoxide-Directed Disulfide-Bond-Forming Reaction
- Total Synthesis of dl-Cepharamine
- Studies on the Alkaloids of Menispermaceous Plants. CCXXXIX. Synthesis of Hasubanan Derivative from Sinomenine.
- Studies on the Alkaloids of Menispermaceous Plants. CCXXXVII. Alkaloids of Stephania japonica MIERS. (Suppl. 17). Structure of Homostephanoline. (3).
- Studies on the Alkaloids of Menispermaceous Plants. CCXXXVIII. Alkaloids of Stephania japonica MIERS. (Suppl. 18). Structure of Hasubanonine (Supplement 1).
- Enzyme Immunoassay of Thyrotropin Releasing Hormone (TRH)
- Syntheses and Biological Activities of Selenium Analogs of α-Rat Atrial Natriuretic Peptide
- Investigation of the Dimethylsulfoxide-Trifluoroacetic Acid Oxidation System for the Synthesis of Cystine-Containing Peptides
- Synthetic Study on Selenocystine-Contaning Peptides
- New Synthetic Routes to (±)-Perhydrohistrionicotoxin. Stereoselective Synthesis of (6S^*, 7S^*, 8S^*)-7-Butyl-8-hydroxy-1-azaspiro [5.5]-undecan-2-one and Its (6R^*)-Isomer
- Synthesis of dl-Pumiliotoxin C Hydrochloride and Its Crystal Structure
- Total Synthesis of the Alkaloid (±)-Metaphanine
- Total Synthesis of the Alkaloid, (±)-Hasubanonine
- Highly Regio- and Stereoselective 1,4-Addition Reaction of β-Cyclopropyl-α, β-enones with Organocopper (I)-Aluminum Trichloride
- Chemical Conversion of Stepinonine to Bisbenzylisoquinoline Alkaloids
- Structure of Stepinonine : a New Dimeric Benzylisoquinoline-2-phenyl-s-homotetrahydroisoquinoline Alkaloid
- Synthesis of Trilobine, Isotrilobine, and Obaberine
- Studies on the Alkaloids of Menispermaceous Plants. CCXV. Alkaloids of Stephania japonica MIERS. (Suppl. 13). Structure of Metaphanine. (2).
- Studies on the Alkaloids of Menispermaceous Plants. CCXIV. Alkaloids of Stephania japonica MIERS. (Suppl. 12). Structure of Metaphanine. (1)
- Studies on the Alkaloids of Menispermaceuos Plants. CCX. Alkaloids of Stephania japonica MIERS. (Suppl. 9). Structure of Hasubanonine and Homostephanoline
- 1,3,8,10,11,14-HEXAZAPENTAPHENE-2,4,7,9(14H___-, 3H___-, 8H___-, 11H___-)-TETRAONES (BENT DOUBLE-HEADED 5-DEAZAFLAVINS) WITH STRONG OXIDIZING POWER
- Reduction-Alkylation with Organocopper(I) Reagents-Alkyl Halides : Highly Regioselective α-Alkylation of γ-Acetoxy-α, β-enoates with Lithium Dibutylcuprate-Alkyl Halides and Difference in the Reactivity of Electron-Deficient Olefins with Organocopper(I)-L
- A New Stereoselective Synthesis of (±)-Perhydrogephyrotoxin
- A CONVENIENT LEWIS ACID CATALYZED PREPARATION OF CARBAMATES FROM SECONDARY ALCOHOLS AND ISOCYANATES
- 有機銅を用いた不斉誘起反応
- Studies on the alkaloids of menispermaceous plants.-237,239-
- 抗HIV薬としてのアンチセンスDNA