SB-203207 and SB-203208, two novel isoleucyl tRNA synthetase inhibitors from a Streptomyces sp. II. Structure determination.
Two novel isoleucyl tRNA synthetase inhibitors, SB-203207 and SB-203208 have been isolated from a Streptomyces sp. and found to be structurally related to altemicidin. Structures of SB-203207 and SB-203208 have been deduced by a combination of spectroscopic techniques, derivatisation, hydrolysis studies and found to be 4-(aminocarbonyl)-7-[[(2-amino-3-methylpentanoyl)aminosul phonyl]acetamido]-2,4a,5,6,7,7a-hexahydro-6-hydroxy-2-methyl-1H-2- pyrindine-7-carboxylic acid (1) and 4-(aminocarbonyl)-7-[[(2-amino-3-methyl pentanoyl)-aminosulphonyl]acetamido]-2,4a,5,6,7,7a-hexahydro-6-(2- amino-3-phenylbutanoyl oxy)-2-methyl-1H-2-pyrindine-7-carboxylic acid (2), respectively.
Houge-Frydrych
C S
CS
SmithKline Beecham Pharmaceuticals, New Frontiers Science Park, Harlow, Essex, UK.
Gilpin
M L
ML
Skett
P W
PW
Tyler
J W
JW
D000470:Alkaloids / Q000737:chemistry*; D000903:Antibiotics, Antineoplastic / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D004791:Enzyme Inhibitors / Q000737:chemistry* / Q000494:pharmacology; D006868:Hydrolysis; D007192:Indenes / Q000737:chemistry* / Q000494:pharmacology; D007533:Isoleucine-tRNA Ligase / Q000037:antagonists & inhibitors; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011725:Pyridines; D013302:Streptomyces; D013449:Sulfonamides / Q000737:chemistry* / Q000494:pharmacology; D013457:Sulfur Compounds
D000470:Alkaloids; D000903:Antibiotics, Antineoplastic; D004791:Enzyme Inhibitors; D007192:Indenes; D011725:Pyridines; C410786:SB 203207; C410787:SB 203208; D013449:Sulfonamides; D013457:Sulfur Compounds; C061865:altemicidin; D007533:Isoleucine-tRNA Ligase