76 免疫増強作用を有する微生物代謝産物Gludapcin(FK-156)の合成
スポンサーリンク
概要
- 論文の詳細を見る
For structural confirmation of FK-156(1), a new immunostimulating peptide isolated from a Streptomyces strain, 1 was synthesized starting from di-Z-meso-diaminopimelic acid(3) via a sequence of reactions involving, as key steps, an enzyme-mediated asymmetric hydrolysis (5→6), followed by carbobenzyloxylation using a copper chalate procedure (6→7). Derivatization of 7 to the dipeptide 13 by the usual procedures and condensation of 13 with the appropriately protected lactoyldipeptide 16, derived via a selective benzylation (14→15), gave 17, which was finally deprotected to afford 1. For acquisition of the sample necessary for detailed biological testing, an improved synthesis of 1 was also established by the enzymatic hydrolysis of 18 to 19, followed by coupling process (20→23) via the N-carboxyanhydride(21), whose preparation simultaneously permitted a selective amino-protection with proper differentiation between the two amino groups in meso-diaminopimelic acid.
- 天然有機化合物討論会の論文
- 1981-09-10
著者
-
宮崎 義雄
藤沢薬品中研
-
岡田 達
Exploratory Research Laboratories Fujisawa Pharmaceutical Co. Ltd.
-
橋本 眞志
Exploratory Research Laboratories Fujisawa Pharmaceutical Co. Ltd.
-
武野 秀一
Exploratory Research Laboratories Fujisawa Pharmaceutical Co. Ltd.
-
Hemmi K
Exploratory Research Laboratories Fujisawa Pharmaceutical Co. Ltd.
-
逸見 恵次
Exploratory Research Laboratories Fujisawa Pharmaceutical Co. Ltd.
-
北浦 良彦
(Present address)Pfizer Central Research
-
中口 修
Exploratory Research Laboratories, Fujisawa Pharmaceutical Co., Ltd.
-
中口 修
藤沢薬品中研
-
橋本 眞志
藤沢薬品中研
-
逸見 恵次
藤沢薬品中研
-
武野 秀一
藤沢薬品中研
-
岡田 達
藤沢薬品中研
-
北浦 良彦
藤沢薬品中研
-
Hashimoto M
Exploratory Research Laboratories Fujisawa Phamaceutical Co. Ltd. :(present Address)tsukuba Research
-
中口 修
藤沢薬品工業
関連論文
- Synthesis of Kifunensine, an Immunomodulating Substrate Isolated from a Microbial Source
- 22 Kifunensineおよび8-epi-kifunensineの合成(口頭発表の部)
- Structure and Synthesis of Nectrisine, a New Immunomodulator Isolated from a Fungus
- Structure of Kifunensine, a New Immunomodulator Isolated from an Actinomycete
- Structure and Synthesis of an Immunoactive Lipopeptide, WS1279,of Microbial Origin
- STRUCTURE AND SYNTHESIS OF AN IMMUNOACTIVE LIPOPEPTIDE, WS1279,OF MICROBIAL ORIGIN
- 4-(1-Benzoylindol-3-yl)butyric Acids and FK143 : Novel Nonsteroidal Inhibitors of Steroid 5α-Reductase (II)
- (1-Benzylinodole-3-yl)alkanoic Acids : Novel Nonsteroidal Inhibitors of Steroid 5α-Reductase (I)
- Flash Photolysis of Allyl Phenyl Ethers
- 4-Azabicyclo [5,2,2] undeca-8,10-dien-3-ones. Photochemical Formations and Novel Rearrangements
- DIASTEREOSELECTIVE SYNTHESIS OF AN α, β-DIAMINOCARBOXYLIC ACID : AN EFFICIENT SYNTHESIS OF FR900490,AN IMMUNOMODULATING PEPTIDE ISOLATED FROM A FUNGUS
- SYNTHESIS OF 1-DEOXYNOJIRIMYCIN AND 1-DEOXYMANNOJIRIMYCIN
- Synthesis and Aldose Reductase-Inhibitory Activities of Structural Analogues of WF-3681,a Novel Aldose Reductase Inhibitor
- Enantioselective Synthesis of Monocyclic β-Lactams Related to Nocardicins via a [2+2] Cycloaddition Reaction(Organic,Chemical)
- Preparation of 3-Aminonocardicinic Acid and Its Acyl Derivatives(Organic,Chemical)
- AN EFFICIENT SYNTHESIS OF WF-3681, A NOVEL ALDOSE REDUCTASE INHIBITOR, AND ITS RELATED COMPOUNDS(Communications to the Editor)
- 43 ペニシリンよりModified β-lactam Antibioticsへの変換
- Synthesis of Some Polyhydroxylated Pyrrolidine Derivatives(Organic,Chemical)
- SYNTHESIS AND ADJUVANT ACTIVITY OF FK-156 ANALOGUES : ACYL DERIVATIVES OF N-[N^2-(L-ALANYL-γ-D-GLUTAMYL)-2 (L), 2'(D)-DIAMINO-1-PIMELOYL] GLYCINE
- Studies on Structure-Activity Relationships of FK-156,an Immunostimulating Peptide, and Related Compounds. II. Synthesis of N^2-(γ-D-Glutamyl)-2 (L), 2' (D)-diaminopimelic Acid as the Minimal Essential Structure of FK-156
- Studies on Structure-Activity Relationships of FK-156,an Immunostimulating Peptide, and Related Compounds. I. Synthesis of Stereoisomeric Analogues of FK-156
- SYNTHESIS AND IMMUNOSTIMULATING ACTIVITY OF FK-156 ANALOGUES : FATTY ACID DERIVATIVES OF N-[N^α-(γ-D-GLUTAMYL)-L-LYSYL]-D-ALANINE
- Studies on Phosphonic Acid Antibiotics. IV. Synthesis and Antibacterial Activity of Analogs of 3-(N-Acetyl-N-hydroxyamino)-propylphosphonic Acid (FR-900098)
- 76 免疫増強作用を有する微生物代謝産物Gludapcin(FK-156)の合成
- Studies on Phosphonic Acid Antibiotics. III. Structure and Synthesis of 3-(N-Acetyl-N-hydroxyamino) propylphosphonic Acid (FR-900098) and 3-(N-Acetyl-N-hydroxyamino)-2 (R)-hydroxypropyl-phosphonic Acid (FR-33289)
- STRUCTURE OF LAVENDOMYCIN, A NEW PEPTIDE ANTIBIOTIC
- Synthesis 8-epi-Kifunensine
- SYNTHESIS OF 8-EPI-KIFUNENSINE
- Synthesis and Characterization of Orally Active Nonpeptide Vasopressin V_2 Receptor Antagonists
- SYNTHESIS OF OPTICALLY ACTIVE β-METHYLTRYPTOPHANS FROM AZIRIDINE-2-CARBOXYLATES
- Photocyclization of N-Chloroacetyl-3-methoxyphenethylamine and N-Chloroacetyl-3,5-dimethoxyphenethylamine.
- SYNTHESIS OF N^7-HYDROXY- AND N^7-METHOXYCEPHALOSPORINS