Studies on Peptides. XXVII. Synthesis of the Decapeptide, ACTH-(5-14), as an Example of Peptide-Fragment Condensation on the Polymer Support
スポンサーリンク
概要
- 論文の詳細を見る
As an example of peptide fragment condensation on the polymer support, synthesis of the tryptophan-containing decapeptide, ACTH-(5-14) was undertaken. First, suitable conditions to esterify Boc-Lys (Z)-Pro-Val-Gly-OH onto the copolymer of styrene and 2% divinylbenzene were examined. At room temperature, fairly good esterification of this tetrapeptide was achieved by the use of the bromomethylated copolymer and dicyclohexylamine. The peptide-resin was then treated with 1N HCl and triethylamine. To the resulting free tetrapeptide-resin, Z-Glu (OBzl)-His-Phe-Arg (NO_2)-Trp-Gly-OH was condensed by means of DCC and the growing peptide resin was treated with HF. The product, H-Glu-His-Phe-Arg-Trp-Gly-Lys-Pro-Val-Gly-OH was obtained simply by column chromatography on CM-cellulose.
- 公益社団法人日本薬学会の論文
- 1970-07-25
著者
-
渡辺 英彦
Faculty of Pharmaceutical Sciences, Kyoto University
-
河谷 紘樹
Faculty of Pharmaceutical Sciences, Kyoto University
-
矢島 治明
Faculty Of Pharmaceutical Sciences Kyoto University
関連論文
- 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
- 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. 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. 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
- SYNTHESIS OF A 42 RESIDUE PEPTIDE CORRESPONDING TO THE ENTIRE AMINO ACID SEQUENCE OF HUMAN GIP
- Studies on Peptides. CL. Syntheses of [D-His^2]-Analogs of Enkephalin and Adrenorphin and Several [D-Arg^2]enkephalin Analogs(Organic,Chemical)
- Studies on Peptides. CXXXIV. : Evaluation of S-1-Adamantylcysteine for Peptide Synthesis
- Studies on Peptides. LXXX. N^G-Mesitylene-2-sulfonylarginine
- Studies on Peptides. LX. Synthesis of the Nonatriacontapeptide corresponding to the Entire Amino Acid Sequence of Bovine Adrenocorticotropic Hormone
- Studies on Peptides. XCVII. Synthesis of Porcine Glu^8-Vasoactive Intestinal Polypeptide (VIP)
- Studies on Peptides. XLI. Synthesis of the Protected Hexadecapeptide Corresponding to Positions 13 to 28 of the Basic Trypsin Inhibitor from Bovine Pancreas (Kunitz and Northrop)
- Studies on Peptides. XXIV. Some Observation on the Urethan Formation during the Mixed Anhydride Procedure in Peptide Synthesis
- Studies on Peptides. XXIII. Total Synthesis of Monkey β-Melanocyte-stimulating Hormone
- Studies on Peptides. XXII. Synthesis of the partially Protected Pentadecapeptide related to Monkey and Human β-Melanocyte-stimulating Hormones
- Studies on Peptides. XVI. Regeneration of Lysine from N^ε-Formyllysine by Aqueous Hydrazine or Hydroxylamine and Their Application to the Synthesis of α-Melanocyte-stimulating Hormone
- Studies on Peptides. XV. Synthesis of Prolyltyrosylarginylmethionine, the Tetrapeptide situated within the Amino Acid Sequences of Monkey and Human β-Melanocyte-stimulating Hormones.
- Studies on Peptides. XIV. Synthesis of Lysyl-S-benzylcysteinylalanylglutaminyl-S-benzyl-cysteinylhistidine, a Peptide related to Horse Heart Cytochrome C.
- Studies on Peptides. XII.Synthesis of the Decapeptide corresponding to the C-Terminal Portion of β-Melanocyte-stimulating Hormone
- Studies on Peptides. VI. Synthesis of Three Stereoisomeric Pentapeptides of Histidylphenyl-alanylarginyltryptophylglycine Possessing D-Phenylalanyl-D-arginyl Moiety within the Sequence and Their Melanocyte-stimulating Activities in vitro
- 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 [27-Tyr]-Cholecystokinin-Pancreozymin (CCK-PZ)
- Studies on Peptides. LVII. Synthesis of the Octadecapeptide corresponding to the Entire Amino Acid Sequence of Equine β-Melanocyte-stimulating Hormone
- Studies on Peptides. LIII. Synthesis of the Docosapeptide Corresponding to the Entire Amino Acid Sequence of Porcine ACTH-Like Intermediate Lobe Peptide (CLIP)
- Studies on Peptides. XLIV. Synthesis of the Basic Trypsin Inhibitor from Bovine Pancreas (Kunitz and Northrop) by the Fragment Condensation Procedure on Polymer Support
- Studies on Peptides. XLIII. Synthesis of Two Protected Peptides Related to the C-Terminal Portion of the Basic Trypsin Inhibitor from Bovine Pancreas (Kunitz and Northrop)
- Studies on Peptides. XLII. Synthesis of the Protected Nonapeptide Corresponding to Positions 29 to 37 of the Basic Trypsin Inhibitor from Bovine Pancreas (Kunitz and Northrop)
- Studies on Peptides. XL. Synthesis of the Protected Dodecapeptide corresponding to Positions 1 to 12 of the Basic Trypsin Inhibitor from Bovine Pancreas (Kunitz and Northrop)
- Studies on Peptides, XXXIX. N-Isobutoxycarbonyl-2-alkoxy-1,2-dihydroquinoline Derivatives, as Coupling Reagents in Peptide Synthesis
- Studies on Peptides. XXXV. Some p-Methoxybenzyloxycarbonyl-Amino Acid Derivatives
- Studies on Peptides. XXXI. Synthesis of Two Model Pentapeptides related to Clostridial Ferredoxin
- Studies on Peptides. XXX. Trichloroethyloxycarbonylhydrazine
- Studies on Peptides. XXIX. p-Methoxybenzyl Mixed Carbonates
- Studies on Peptides. Warning for the Explosive Carbazide Formation during the Direct Preparation of t-Butyl Azidoformate or p-Methoxybenzyl Azidoformate
- Studies on Peptides. XXV. A Convenient Procedure for the Preparation of p-Methoxybenzyl Azidoformate
- Studies on Peptides. CXLVI. : Synthesis of Gln^-Motilin and Examination of Its Immunological Properites
- Studies on Peptides. CXLV. : Synthesis of a 27-Residue Peptide Amide Corresponding to the Entire Amino Acid Sequence of Canine Gastrin-Releasing Polypeptide (cGRP)
- Studies on Peptides. CXL. : Synthesis of Human Gastrin-Releasing Polypeptide (hGRP)
- Studies on Peptides. CXXX. Convenient Procedure for the Reduction of Methionine Sulfoxide
- SYNTHESIS OF A 27-RESIDUE PEPTIDE CORRESPONDING TO THE ENTIRE AMINO ACID SEQUENCE OF HUMAN GASTRIN-RELEASING PEPTIDE (hGRP)
- Studies on Peptides. CV. Synthesis of Chicken Neurotensin
- Synthesis and Biological Activity of 8-L-Ala-Motilin and 8-D-Ala-Motilin
- 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
- Studies on Peptides. CI. Synthesis of a Wasp Venom, Mastoparan M
- Synthesis of Granuliberin-R and Various Fragment Peptides and Their Histamine-Releasing Activities
- Synthesis of the Dodecapeptide Amide corresponding to the Entire Amino Acid Sequence of Granuliberin-R, a New Frog Skin Peptide from Rana rugosa
- Synthesis of Granuliberin-R, a New Frog Skin Peptide from Rana rugosa
- Circular Dichroism of Active Fragments of α-Melanocyte-stimulating Hormone
- Studies on Peptides. CX. Solution Synthesis of the Tetratriacontapeptide Amide corresponding to Positions 1 to 34 of Human Parathyroid Hormone
- Studies on Peptides. CIX. Synthesis of the Octatriacontapeptide Corresponding to Positions 1 to 38 of Human Parathyroid Hormone
- Synthesis of the Nonacosapeptide corresponding to Mammalian Glucagon
- Synthesis of Porcine Motilin and Its D-Phe^1-Analog by the Use of Methanesulfonic Acid
- 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
- 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)
- 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. CXXXVII. : Conventional Solution Synthesis of Porcine Hypothalamic Growth Hormone Releasing Factor (pGRF)
- Further Synthesis of Enkephalinol Analogs containing the Dipeptide Unit Tyr-Arg (Kyotorphin)
- Convenient Procedure for the Preparation of α-Amino Alcohols
- Enkephalin Analogs Containing the Dipeptide Unit Tyr-Arg (Kyotorphin)
- Synthesis of Two Peptides corresponding to α-Endorphin and γ-Endorphin by the Methanesulfonic Acid Deprotecting Procedure
- Synthesis of the Untriacontapeptide corresponding to the Entire Amino Acid Sequence of Human β-Endorphin
- Synthesis of the Protected Octadecapeptide corresponding to the Amino Acid Sequence [14-31] of Human β-Endorphin
- Synthesis of the Pentadecapeptide corresponding to the Entire Amino Acid Sequence of Salmon α-Melanotropin II (α-MSH II)
- Solution Synthesis of a Heptacosapeptide known as Bovine γ_3-Melanotropin (γ_3-MSH)
- Studies on Peptides. XXVIII. Synthesis of the Docosapeptide which Embodies the Entire Amino Acid Sequence of β-Melanocyte-stimulating Hormone from Human Pituitary Gland
- Studies on Peptides. LXI. Alternate Synthesis of Human Corticotropin (ACTH)
- Studies on Peptides. XXXIII. N^ε-β, β, β-Trichloroethyloxycarbonyllysine
- Studies on Peptides. XLVI. Synthesis of Human Type Corticotropinlike Intermediate Lobe Peptide (CLIP)
- Studies on Peptides. LIV. Synthesis of the Protected Tetradecapeptide corresponding to Positions 9 through 22 of Porcine Motilin, a Gastric Motor Activity Stimulating Polypeptide
- Studies on Peptides. XLV. Synthesis of the Bovine Type Corticotropin-like Intermediate Lobe Peptide (CLIP)
- Studies on Peptides. XXXII. The Use of N-Ethoxycarbonyl-2-ethoxy-1,2-dihydro-quinoline as a Coupling Reagent of Peptide-Fragments on Polymer Support
- Studies on Peptides. XXVII. Synthesis of the Decapeptide, ACTH-(5-14), as an Example of Peptide-Fragment Condensation on the Polymer Support
- Studies on Peptides. XXVI. Application of the Solid Phase Peptide Synthesis to the Screening Test of an Active Fragment proposed for Parathyroid Hormone
- A Convenient Method for the Preparation of tert-Butyl Azidoformate