Synthesis of a Highly Potent Analog of Luteinizing Hormone Releasing Hormone (LH-RH) : [Des-Gly-NH_2^<10>, Pro-NH-Et^9]-LH-RH

スポンサーリンク

概要

• 論文の詳細を見る

• A highly potent analog of luteinizing hormone releasing hormone (LH-RH), pGlu-His-Trp-Ser-Tyr-Gly-Leu-Arg-Pro-NHCH_2-CH_3 was synthesized by the conventional solution method. The key intermediate, H-Leu-Arg (NO_2)-Pro-NHCH_2-CH_3,which was prepared by the stepwise manner using the activated esters of the corresponding protected amino acids, was coupled with N-terminal hexapeptide, pGlu-His-Trp-Ser-Tyr-Gly-OH, by the HONB/DCC method to give the mono-protected nonapeptide ethylamide. The protected peptide was treated with stannous chloride in 60% aqueous formic acid to remove the nitro group. The purification of the resulting peptide was carried out by a column chromatography on Amberlite XAD-2 and followed by a column chromatography on carboxymethylcellulose. The synthetic method described is promising for preparing this analog of LH-RH in large quantities and good quality.

• 公益社団法人日本薬学会の論文
• 1975-01-25

著者

• 藤野 政彦

  Chemistry Laboratories Central Research Division Takeda Chemical Industries Ltd.

• 藤野 政彦

  Medicinal Research Laboratories, Central Research Division, Takeda Chemical Industries, Ltd.

• 品川 進

  Medicinal Research Laboratories, Central Research Division, Takeda Chemical Industries, Ltd.

関連論文

• Studies on Peptides. CXXXIV. : Evaluation of S-1-Adamantylcysteine for Peptide Synthesis
• The Synthesis of Serum Thymic Factor and Its Analogs
• Synthesis and Pharmacology of TRH Analogs to separate Central Nervous Action from Endocrine Activity
• New Method for Removing the S-p-Methoxybenzyl and S-t-Butyl Groups of Cysteine Residues with Mercuric Trifluoroacetate
• p-Methoxybenzenesulfonyl as a Protecting Group of Guanidino Function in Peptide Synthesis
• Synthesis of Peptides related to Corticotropin (ACTH). IX. Application of N-Hydroxy-5-norbornene-2,3-dicarboximide Active Ester Procedure to the Synthesis of Human Adrenocorticotropic Hormone (α_h-ACTH)
• Synthesis of Peptides related to Corticotropin (ACTH). VIII. Synthesis of α^-ACTH
• The Use of N-Hydroxy-5-norbornene-2,3-dicarboximide Active Esters in Peptide Synthesis
• Isobornyloxycarbonyl Function, a New Convenient Amino-Protecting Group in Peptide Synthesis. I. Synthesis and Properties of Isobornyloxycarbonylamino Acids
• Synthesis of Peptides related to Corticotropin (ACTH). VII. Syntheses and Biological Activity of Leucine^7-α^-ACTH and N^α-Methyltryptophan^9-α^-ACTH
• Synthesis of Peptides Related to Corticotropin (ACTH). VI. Syntheses and Biological Activity of the Peptides Corresponding to the Amino Acid Sequences 4-23,5-23,6-24 and 7-23 in ACTH
• Synthesis of Peptides related to Corticotropin (ACTH). V. Syntheses of Leucine^4- and Isoleucine^4-α^-ACTH
• Synthesis of Peptides related to Corticotropin (ACTH). IV. Syntheses of β-Alanine^1-, γ-Aminobutyric Acid^1-, Sarcosine^1-, Proline^1- and Lysine^1-α^-ACTH
• Synthesis of Peptides related to Corticotropin (ACTH). III. Syntheses of α^_2-ACTH and β-Alanine^1-α^_2-ACTH
• Synthesis of Peptides related to Corticotropin (ACTH). I. Synthesis of α^_2-ACTH-tricosapeptide Amide
• Synthesis of Peptides related to Corticotropin (ACTH). II. Synthesis of the Protected Peptides Corresponding to the Sequence 1-3,4-6,7-10,11-14,15-19 and 20-23 of ACTH
• The Use of Esters of Simple Ketoximes in Peptide Synthesis
• Synthesis of Some Di-and Tri-Substituted Analogs of Luteinizing Hormone Releasing Hormone (LH-RH)
• Isobornyloxycarbonyl Function, a New Convenient Amino-Protecting Group in Peptide Synthesis.IV. Synthesis of Gonadotropin-Releasing Hormone (Gn-RH or LH-RH/FSH-RH)
• Synthesis and Biological Activity of 8-L-Ala-Motilin and 8-D-Ala-Motilin
• A New Mast Cell Degranulating Peptide "Mastoparan" in the Venom of Vespula lewisii
• 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
• 4-Methoxy-2,3,6-trimethylbenzenesulfonyl (Mtr) : a New Amino and Imidazole Protecting Group in Peptide Synthesis
• Synthesis of the Heptadecapeptide corresponding to the Full Sequence of Dynorphin
• Further Studies on the Use of Multi-substituted Benzenesulfonyl Groups for Protection of the Guanidino Function of Arginine
• Use of the 4-Methoxy-2,6-dimethylbenzenesulfonyl (Mds) Group to Synthesize Dynorphin [1-13] and Related Peptides
• New Peptide Models for Studying Racemization
• New Protecting Groups for the Indole Ring of Tryptophan in Peptide Synthesis : 2,4,6-Trimethoxybenzenesulfonyl and 4-Methoxy-2,3,6-trimethylbenzenesulfonyl Groups
• Synthesis of a Wasp Venom Tetradecapeptide, Mastoparan, with a New Cleaving System for 4-Methoxy-2,3,6-trimethylbenzenesulfonyl (Mtr) Amino-Protecting Group
• A New Procedure for the Pentachlorophenylation of N-Protected Amino Acids
• A New Reagent for the tert-Butyloxycarbonylation of Amino Acids
• Synthetic Studies on Enkephalin Analogs. II. Enhanced Analgesic Activity of H-Tyr-D-Ala-Gly-Phe-NHNH-CO-CH_2CH_3 following N-Methylation of Tyr and Phe
• Synthetic Studies on Enkephalin Analogs. I. Potent Analgesic Activity of H-Tyr-D-Ala-Gly-Phe-NHNH-CO-R (R=Lower Alkyl)
• Synthesis of a Highly Potent Analog of Luteinizing Hormone Releasing Hormone (LH-RH) : [Des-Gly-NH_2^, Pro-NH-Et^9]-LH-RH
• Isobornyloxycarbonyl Function, a New Convenient Amino-Protecting Group in Peptide Synthesis. II. Synthesis of Bradykinin

もっと見る 閉じる

スポンサーリンク