Isolation and Structure of Leukotriene-A4 Hydrolase Inhibitor: 8(S)-Amino-2(R)-methyl-7-oxononanoic Acid Produced by Streptomyces diastaticus

The novel amino acid 8(S)-amino-2(R)-methyl-7-oxononanoic acid (1) was isolated from the soil-borne microorganism Streptomyces diastaticus during our screening for inhibitors of leukotriene-A4 hydrolase (LTA4H), a requisite enzyme in the biosynthesis of the potent inflammatory mediator leukotriene-B...

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Veröffentlicht in:	Journal of natural products (Washington, D.C.) D.C.), 1996-10, Vol.59 (10), p.962-964
Hauptverfasser:	Parnas, Barry L, Durley, Richard C, Rhoden, Eric E, Kilpatrick, Brian F, Makkar, Narinder, Thomas, Kristin E, Smith, Walter G, Corley, David G
Format:	Artikel
Sprache:	eng
Schlagworte:	ACIDE AMINE AMINO ACIDS AMINOACIDOS Angiotensin-Converting Enzyme Inhibitors - pharmacology Animals Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents Applied microbiology BACTERIA BIOASSAYS Biological and medical sciences BIOSINTESIS BIOSYNTHESE BIOSYNTHESIS Biotin - metabolism CHEMICAL COMPOSITION CHEMICAL STRUCTURE COMPOSICION QUIMICA COMPOSITION CHIMIQUE DOSAGE BIOLOGIQUE DOSAGE EFFECTS EICOSANOIDE EICOSANOIDES EICOSANOIDS ENSAYO BIOLOGICO ENZYME INHIBITORS Enzyme Inhibitors - chemistry Enzyme Inhibitors - isolation & purification Enzyme Inhibitors - pharmacology Epoxide Hydrolases - antagonists & inhibitors ESPECTROMETRIA ESTRUCTURA QUIMICA Fatty Acids - chemistry Fatty Acids - isolation & purification Fatty Acids - pharmacology FLORA DEL SUELO FLORE DU SOL Fundamental and applied biological sciences. Psychology General aspects HIDROLASAS Humans HYDROLASE HYDROLASES INFLAMACION INFLAMMATION INHIBIDORES DE ENZIMAS INHIBITEUR D'ENZYME Leukotriene B4 - biosynthesis Leukotriene B4 - blood LEUKOTRIENE-B4 Microbiology Protease Inhibitors - chemistry Protease Inhibitors - pharmacology Rabbits SOIL FLORA SPECTRAL ANALYSIS SPECTROMETRIE SPECTROMETRY STREPTOMYCES Streptomyces - chemistry Streptomyces - metabolism STRUCTURE CHIMIQUE Thromboxane B2 - biosynthesis Thromboxane B2 - blood
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Beschreibung
Zusammenfassung:	The novel amino acid 8(S)-amino-2(R)-methyl-7-oxononanoic acid (1) was isolated from the soil-borne microorganism Streptomyces diastaticus during our screening for inhibitors of leukotriene-A4 hydrolase (LTA4H), a requisite enzyme in the biosynthesis of the potent inflammatory mediator leukotriene-B4 (LTB4). The structure of 1 was determined by detailed spectroscopic analyses and is related to 7-keto-8-aminopelargonic acid (2), a biosynthetic precursor of biotin. The relative potency of 1 (LTA4H IC50 = 0.6 μM) warranted further biological studies.
ISSN:	0163-3864 1520-6025
DOI:	10.1021/np9603986