87 高等植物由来の鉄輸送キレート剤ムギネ酸類の合成研究(ポスター発表の部)

スポンサーリンク

概要

• 論文の詳細を見る

• Mugineic acid (1) is a typical phytosiderophore that is excreted from roots of barley and promotes uptake and transport of iron in higher plants. Interestingly, it is reported that mugineic acid (1) exerts an inhibitory effect aganist angiotensin-converting enzyme. Mugineic acid (1) is required in quantities for the physiological studies of higher plants since it is produced only a minute amount in Nature. Similar iron-chelating amino acids have been also isolated from some species of gramineous plants: 3-epihydroxymugineic acid (2) and disticonic acid A (3) from beer barley and have the same iron-chelating activity as that of mugineic acid (1). Although the synthesis of mugineic acid (1) have been reported from our laboratories, their synthetic routes are not suitable for the large scale production of 1, because of their low yields and selectivity. Herein, we report an efficient stereoselective total synthesis of 1 and the first total synthesis of 2 and 3, which started from readily available (2R,3R)- and (2S,3S)-epoxycinnamyl alcohol employing the phenyl group as the carboxylic synthon. Preparation of β-hydroxyhomoserine derivative 14 was performed in 10 steps from (2R,3R)-epoxy alcohol 7, utilizing the ruthenium tetroxide oxidation as a key reaction. The aldehyde 17, the right constituent of 1, was prepared from (2S,3S)-epoxy alcohol 8 by the similar methodology as the preparation of 14. (S)- Azetidine carboxylic acid (4) was transformed to its tert-butyl ester acetate 18. The above three components were stepwisely coupled by the reductive N-alkylation with sodium cyanoborohydride. After deprotection and purification, we succeeded in the synthesis of mugineic acid (1). 3-Epi-hydroxymugineic acid (2) and disticonic acid A (3) were also prepared from the key intermediate 14 through the analogeous reaction sequences by use of the β-hydroxyhomoserine derivative 26 and glycine tert-butyl ester acetate 31, respectively, instead of azetidine carboxylic acid derivative 18.

• 天然有機化合物討論会の論文
• 1992-09-10

著者

• 濱田 康正

  名市大・薬

• 塩入 孝之

  名市大・薬

• 塩入 孝之

  名城大院・総合学術

• 塩入 孝之

  名古屋市大・薬

• 濱田 康正

  Faculty of Pharmaceutical Sciences, Nagoya City University

• 松浦 史義

  名市大・薬

• 濱田 康正

  Faculty Of Pharmaceutical Sciences Nagoya City University

関連論文

• 82 海洋産抗腫瘍活性物質カリクリン類の合成研究(口頭発表の部)
• Total Synthesis of Avellanins A and B, New Fungal Metabolites from Hamigera avellanea with Pressor Effect
• New Methods and Reagents in Organic Synthesis. 43. A New Synthesis of tert-Butyl Peroxycarboxylates Using Diethyl Phosphorocyanidate (DEPC)
• New Methods and Reagents in Organic Synthesis. 15. Epoxidation of Olefins with Diethyl Phosphorocyanidate (DEPC) and Hydrogen Peroxide
• 9-4 鉄欠乏オオムギ根で誘導されるアルコールデヒドロゲナーゼ遺伝子について(9.植物の無機栄養)
• 16 鉄欠乏オオムギ根で発現するムギネ酸鉄トランスポーター遺伝子のスクリーニング法の検討(関東支部講演会)
• Molecular Conformation of Patellamide A, a Cytotoxic Cyclic Peptide from the Ascidian Lissoclinum patella, by X-Ray Crystal Analysis
• 36 海洋産抗腫瘍性環状ペプチドパテラマイド類の全合成
• 15 Evans-Aldol反応を鍵工程とするドラスタチン10の立体選択的全合成(口頭発表の部)
• ムギネ酸生合成経路の研究 : ニコチアナミンアミノ基転移酵素の精製
• 19 環状ヘミアミナール構造を有する大環状デプシペプチドの合成研究 : 海洋藍藻由来のソママイドAの全合成(口頭発表の部)
• 94(P-51) 海洋産微生物由来抗炎症活性環状ペプチド、サイクロマリンAの合成研究(ポスター発表の部)
• 116(P-48) 海産藍藻由来神経毒カルキトキシンの全合成研究(ポスター発表の部)
• 30 海洋ラン藻Lyngbya majusculaから得られた神経毒kalkitoxin(口頭発表の部)
• 海産藍藻由来魚毒活性物質アンチラトキシンの全合成
• 1 海洋産チアゾール含有ポリケチド,マイコチアゾールの合成研究(口頭発表の部)
• 異常アミノ酸を含有するペプチドの合成--ドラスタチン10を例として (生命科学を指向したペプチド合成の進歩)
• 17 カリクリン類の合成研究(口頭発表の部)
• 87 高等植物由来の鉄輸送キレート剤ムギネ酸類の合成研究(ポスター発表の部)
• 海洋起源生物活性ペプチドの合成 (化学で探る海洋生物の謎) -- (海洋に医薬をもとめて)
• 新規有機合成反応剤の開発とその生理活性天然有機化合物合成への応用
• New Methods and Reagents in Organic Synthesis. 69. A New Synthesis of α-Amino Acid and Peptide Amides of Aromatic Amines Using a Modified Curtius Reaction with Diphenyl Phosphorazidate(Organic,Chemical)
• 海洋産抗腫瘍活性環状ペプチドの合成研究
• NEW METHODS AND REAGENTS IN ORGANIC SYNTHESIS. 57. A STEREOSELECTIVE SYNTHESIS OF A DERIVATIVE OF D-RISTOSAMINE
• 62 ティリバリンの立体選択的全合成
• 37 Sulfobacin類の全合成(口頭発表の部)
• NEW METHODS AND REAGENTS IN ORGANIC SYNTHESIS. 47. A GENERAL, EFFICIENT, AND CONVENIENT SYNTHESIS OF DIARYLHEPTANOIDS
• Formation and Decomposition of 1,2,3-Triazolines Prepared from Diphenyl Phosphorazidate (DPPA) and Enamines of Diaryl-Type Ketones
• NEW METHODS AND REAGENTS IN ORGANIC SYNTHESIS. 44. A NEW GENERAL EFFICIENT SYNTHESIS OF DL-[N]-GINGEROLS AND RELATIVES THROUGH DIRECT C-ACYLATION USING DIETHYL PHOSPHOROCYANIDATE (DEPC)
• New Methods and Reagents in Organic Synthesis. 35. A New Synthesis of Some Non-Steroidal Anti-Inflammatory Agents with the 2-Arylpropionic Acid Skeleton by the Use of Diphenyl Phosphorazidate (DPPA) as a 1,3-Dipole
• A Resin-promoted Williamson's Alkyl Aryl Ether Synthesis. Methylation of 2-tert-Butyl-5-methylphenol with Methyl Chloride
• 異常アミノ酸を含有するペプチドの合成-ドラスタチン10を例として-
• 海洋産抗腫瘍活性環状ペプチドの合成研究
• CYANOPHOSPHORYLATION OF KETONES AND ALDEHYDES USING DIETHYL PHOSPHOROCYANIDATE (DEPC)
• An Extensive Survey by the Use of High Performance Liquid Chromatography on Racemization during the Coupling of Benzyloxycarbonyl-L-phenylalanyl-L-valine with L-Proline tert-Butyl Ester
• NEW METHODS AND REAGENTS IN ORGANIC SYNTHESIS. 29. A PRACTICAL METHOD FOR THE PREPARATION OF OPTICALLY ACTIVE n-PROTECTED α-AMINO ALDEHYDES AND PEPTIDE ALDEHYDES
• 78 ジフェニルリン酸アジド、ジエチルリン酸シアニドを用いるC-アシル化反応 : 2,4-ジアミノ糖プルマイシン合成への応用
• New Methods and Reagents in Organic Synthesis. 9. C-Acylation of Nitromethane with Aromatic Carboxylic Acids using Diethyl Phosphorocyanidate (DEPC)
• チオシアネートの合成法最近の進歩
• Amino Acids and peptides. XXVI. Phosphorus in Organic Synthesis. XV. Application of Diphenyl Phosphorazidate (DPPA) and Diethyl Phosphorocyanidate (DEPC) to the Synthesis of the N-Terminal Decapeptide of Gastric Inhibitory Polypeptide
• Amino Acids and Peptides. XXV. Phosphorus in Organic Synthesis. XIV. Application of Diphenyl Phosphorazidate (DPPA) to the Synthesis of the N-Terminal Hexapeptide of the Vasoactive Intestinal Peptide
• タイトル無し

もっと見る 閉じる

スポンサーリンク