Studies on Peptides. CXXI. N^<in>-Mesitylenesulfonyl-tryptophan, a New Derivative for Peptide Synthesis

スポンサーリンク

概要

• 論文の詳細を見る

• The mesitylenesulfonyl (Mts) group was introduced at the N^<in> of tryptophan by Illi's method. This group is stable under various conditions required for practical peptide synthesis, such as treatments with dil. alkali, hydrazine hydrate, TFA and even 4 N HCl-dioxane or 25% HBr-AcOH. HF is not able to remove this protecting group, but it can be smoothly cleaved by 1 M trifluoromethanesulfonic acid/TFA or methanesulfonic acid. The usefulness of this new tryptophan derivative, Trp (Mts), for practical peptide synthesis was demonstrated by the synthesis of cholecystokinin-heptapeptide as an example.

• 公益社団法人日本薬学会の論文
• 1984-07-25

著者

• 二木 史朗

  徳島大学薬学部

• 二木 史朗

  Faculty Of Pharmaceutical Sciences The University Of Tokushima

• 藤井 信孝

  Faculty of Pharmaceutical Sciences, Kyoto University

• 矢島 治明

  Faculty of Pharmaceutical Sciences, Kyoto University

• 安村 貢一

  Fujii, Memorial Research Institute, Otsuka Pharmaceutical Co., Ltd.,

• 矢島 治明

  京都大学

• 矢島 治明

  京大・薬

• 藤井 信孝

  京大 薬

• 矢島 治明

  Faculty Of Pharmaceutical Sciences Kyoto University

• 二木 史朗

  Faculty Of Pharmaceutical Sciences Kyoto University

• 安村 貢一

  Faculty of Pharmaceutical Sciences, Kyoto University

• 安村 貢一

  Fujii Memorial Research Institute Otsuka Pharmaceutical Co. Ltd.

関連論文

• 抗アレルギー薬の研究(第1報)1,2,3-三置換-2-propen-1-one類, 3,4-二置換-4-oxo-2-butenoic Acid類及び関連化合物について
• 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
• Studies on Peptides. Application of Trifluoromethanesulphonic Acid as a Deblocking Reagent to the Synthesis of Neurotensin
• Studies on Peptides. LXIV. Synthesis of the Tritetracontapeptide corresponding to the Entire Amino Acid Sequence of Porcine Gastric Inhibitory Polypeptide (GIP)
• Synthesis of Amaryllidaceae Alkaloids, (±)-Cherylline and (±)-Latifine
• Synthesis of Protegrin-Related Peptides and Their Antibacterial and Anti-human Immunodeficiency Virus Activity
• Solution Synthesis of Human Peptide YY (hPYY)
• Solution Synthesis of Human Neuropeptide Y (hNPY)
• 2-Propen-1-one 誘導体の合成と抗真菌活性^
• 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. XCIV. Synthesis and Activity of Kyotorphin and Its Analogs
• Studies on Peptides. LXXIX. : By-Products derived from N^α-Protected Tryptophan by Acids
• Studies on Peptides. LXXVIII. Synthesis of the Nonacosapeptide corresponding to the Entire Amino Acid Sequence of Avian Glucagon (Duck)
• Studies on Peptides. LXXVII. Synthesis of the Protected Heptadecapeptide corresponding to Positions 13-29 of Avian Glucagon (Duck)
• 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. LXX. Synthesis of Two Octadecapeptides corresponding to the Entire Amino Acid Sequence of Camel β-Melanocyte-stimulating Hormones
• Studies on Peptides. LXIX. Selective Removal of Acid Labile α-Amino Protecting Groups with Dilute Sulfonic Acids
• Studies on Peptides. LXIII. Synthesis of the Octacosapeptide Corresponding to Positions 1 through 28 of Porcine Gastric Inhibiting Polypeptide (GIP)
• Studies on Peptides. LXII. Synthesis of the Protected Octadecapeptide corresponding to Positions 26 through 43 of Porcine Gastric Inhibitory Polypeptide (GIP)
• Studies on Peptides. XLIX. Synthesis of the Octadecapeptide corresponding to the Entire Amino Acid Sequence of Porcine β-Melanocyte-stimulating Hormone
• 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
• 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
• 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
• 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 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)
• 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
• 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)
• Studies on Peptides. CLXIV. : Solution-Phase Synthesis of a 36-Residue Peptide Amide Corresponding to the Entire Amino Acid Sequence of Chicken Antral Peptide
• Studies on Peptides. CLX. : Synthesis of a 33-Residue Peptide Corresponding to the Entire Amino Acid Sequence of Human Cholecystokinin (hCCK-33)
• 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
• Enzyme Immunoassay of a Substance P-like Immunoreactive Substance in Human Plasma and Saliva
• Micro-Enzyme Immunoassay of Vasoactive Untestinal Polypeptide (VIP)-like Immunoreactive Substance in Bovine Milk
• Studies on Peptides. CLXVIII. : Syntheses of Three Peptides Isolated from Horseshoe Crab Hemocytes, Tachyplesin I, Tachyplesin II, and Polyphemusin I
• Studies on Peptides. CLXVII. / Solid-Phase Syntheses and Immunological Properties of Fragment Peptides Related to Human Malaria Circumsporozoite Protein
• 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. CLXV. : Combination of a New Amide-Precursor Reagent and Trimethylsilyl Bromide Deprotection for the 9-Fluorenylmenthyloxycarbonyl-Based Solid-Phase Synthesis of chicken Antral Peptide
• Studies on Peptides. CLXIII. : Synthesis of Guinea Pig Vasoactive Intestinal Polypeptide(gVIP)
• Studies on Peptides. CLXII. : Synthesis of Chicken Calcitonin-Gene-Related Peptide (cCGRP) by Application of Sulfoxide-Directed Disulfide-Bond-Forming Reaction
• Studies on Peptides. CLIX. : Preparation of a Protected 33-Residue Peptide for the Synthesis of Human Cholecystokinin (hCCK-33)
• Partical Structural Revision of Porcine Pancreatic Colipase
• Studies on Peptides. CVI. Synthesis of a Physalaemin-like Peptide, [Lys^5,Thr^6]-Physalaemin, isolated from the Skin of a Frog, Uperoleia rugosa
• Enzyme Immunoassay of Thyrotropin Releasing Hormone (TRH)
• Apparent Autolysis of the N-Terminal Tetrapeptide of Vasoactive Intesinal polypeptide (VIP)
• 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
• Studies on Peptides. CXXIX. Application of N^-Mesitylenesulfonyl-tryptophan for the Syntheses of Neuromedin B and Neuromedin C
• Studies on Peptides. CXXVII. Synthesis of a Tripentacontapeptide with Epidermal Growth Factor Activity
• Studies on Peptides. CXII. Alternative Synthesis of Heptacosapeptide, a New Gastrointestinal Polypeptide
• Studies on Peptides. LXXIV. Convenient Procedure for the Preparation of Methionine Sulphoxide Derivatives
• Studies on Peptides. LXXII. Examination of the N^ε-Alkylation of Lysine in the Methanesulphonic Acid Procedure for Peptide Synthesis
• Studies on Peptides. CXX. Synthesis of Growth Hormone Releasing Factor (GRF-37-NH_2) and N^α-Biotinyl-GRF-44-NH_2
• Studies on Peptides. CXIX. Synthesis of Growth Hormone Releasing Factor (hpGRF-40-OH)
• 第31回ペプチド化学討論会
• Facile Reduction of Methionine Sulfoxide with Sulfur Trioxide/Iodide Ion System
• Solution Syntheses of Two Enkephalin-Containing Peptides, Peptide E and Dynorphin(1-24), Using N^-(2,4,6-Triisopropylphenylsulfonyl)tryptophan
• Alternative Synthesis of Porcine Secretin and Apparent Autolysis of the Product
• Studies on Peptides. CXVI. Synthesis of the Protected Docosapeptide Corresponding to the C-Terminal Portion of Human Growth Hormone Releasing Factor (GRF, Somatocrinin)
• Studies on Peptides. XCVI. Behavior of S-Acetamidomethylcysteine Sulfoxide under Deprotecting Conditions in Peptide Synthesis
• Studies on Peptides. LXXXIII. Behavior of S-Substituted Cysteine Sulfoxides under Deprotecting Conditions in Peptide Synthesis
• Behaviour of S-Substituted Cysteine Sulfoxide under Acidolytical Deprotecting Conditions
• Studies on Peptides. L. Acidolysis of Protecting Groups in Peptide Chemistry by Fluorosulphonic Acid and Methanesulphonic Acid
• 合成ペプチドによるイオンチャネル機能の創出
• Studies on Peptides. CXXII. N-Succinimidyl-p-(2-nitrovinyl)-benzoate and Its m-Isomer, as Heterobifunctional Conjugating Reagents for Immunoassay
• Studies on Peptides. CXXI. N^-Mesitylenesulfonyl-tryptophan, a New Derivative for Peptide Synthesis
• Studies on Peptides. CXLIX. : Solid-Phase Synthesis of a Rabbit Stomach Peptide by Application of a New Polymer Support and a New Deprotecting Procedure(Organic,Chemical)
• Studies on Peptides. CXVIII. Synthesis of a Hybrid Growth Hormone Releasing Factor (GRF)-PHI Heptacosapeptide Amide
• Studies on Peptides. CVII. Synthesis of Urotensin II
• Studies on Peptides. CXXV. 3-(3-p-Methoxybenzylthiopropionyl)-thiazolidine-2-thione and Its Analogs as Reagents for the Introduction of the Mercapto Group into Peptides and Proteins
• Studies on Peptides. CXXVI. Synthesis of the Protected Tetracosapeptide Corresponding to Positions 30-53 of Mouse Epidermal Growth Factor (EGF)
• Studies on Peptides. XCIV. Thiazoline-2-thione as a Carboxyl-activating Reagent for Petide Synthesis
• Studies on Peptides. LI. Application of the Solid Phase Synthesis for the Preparation of Pro-Analogues of LH and FSH Releasing Hormone
• Fmoc固相合成法による硫酸化チロシン含有ペプチドの直接合成法の開発
• “Safety-catch”型保護基の特性を活用した硫酸化チロシン含有ペプチドの新規合成法の開発
• Evaluation of the Final Deprotection System for the Solid-Phase Synthesis of Tyr(SO_3H)-Containing Peptides with 9-Fluorenylmethyloxycarbonyl (Fmoc)-Strategy and Its Application to the Synthesis of Cholecystokinin (CCK)-12
• Studies on Peptides. CIV. Synthesis of Ribonuclease S'

もっと見る 閉じる

スポンサーリンク