SB-203207 and SB-203208, two novel isoleucyl tRNA synthetase inhibitors from a Streptomyces sp II.: Structure determination

被引:47
作者
Houge-Frydrych, CSV [1 ]
Gilpin, ML [1 ]
Skett, PW [1 ]
Tyler, JW [1 ]
机构
[1] SmithKline Beecham Pharmaceut, Harlow CM19 5AW, Essex, England
关键词
D O I
10.7164/antibiotics.53.364
中图分类号
Q81 [生物工程学(生物技术)]; Q93 [微生物学];
学科分类号
071005 ; 0836 ; 090102 ; 100705 ;
摘要
Two novel isoleucyl tRNA synthetase inhibitors, SE-203207 and SE-203208 have been isolated from a Streptomyces sp. and found to be structurally related to altemicidin. Structures of SE-203207 and SE-203208 have been deduced by a combination of spectroscopic techniques, derivatisation, hydrolysis studies and found to be 4-(aminocarbonyl)-7-{[(2-amino-3 -methylpentanoyl)aminosulphonyl]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.
引用
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页码:364 / 372
页数:9
相关论文
共 9 条
  • [1] BIRNBAUM GI, 1987, HETEROCYCLES, V25, P493
  • [2] STUDIES OF UNUSUAL AMINO-ACIDS AND THEIR PEPTIDES .6. SYNTHESES AND OPTICAL RESOLUTIONS OF BETA-METHYLPHENYLALANINE AND ITS DIPEPTIDE PRESENT IN BOTTROMYCIN
    KATAOKA, Y
    SETO, Y
    YAMAMOTO, M
    YAMADA, T
    KUWATA, S
    WATANABE, H
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1976, 49 (04) : 1081 - 1084
  • [3] TOTAL SYNTHESIS OF (-)-ALTEMICIDIN - A NOVEL EXPLOITATION OF THE POTIER-POLONOVSKI REARRANGEMENT
    KENDE, AS
    LIU, K
    BRANDS, KMJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (42) : 10597 - 10598
  • [4] APPLICATIONS OF FAST-ATOM-BOMBARDMENT MASS-SPECTROMETRY AND FAST-ATOM-BOMBARDMENT MASS-SPECTROMETRY - MASS-SPECTROMETRY TO THE MADURAMICINS AND OTHER POLYETHER ANTIBIOTICS
    SIEGEL, MM
    MCGAHREN, WJ
    TOMER, KB
    CHANG, TT
    [J]. BIOMEDICAL AND ENVIRONMENTAL MASS SPECTROMETRY, 1987, 14 (01): : 29 - 38
  • [5] SB-203207 and SB-203208, two novel isoleucyl tRNA synthetase inhibitors from a Streptomyces sp I.: Fermentation, isolation and properties
    Stefanska, AL
    Cassels, R
    Ready, SJ
    Warr, SR
    [J]. JOURNAL OF ANTIBIOTICS, 2000, 53 (04) : 357 - 363
  • [6] ALTEMICIDIN, A NEW ACARICIDAL AND ANTITUMOR SUBSTANCE .1. TAXONOMY, FERMENTATION, ISOLATION AND PHYSICOCHEMICAL AND BIOLOGICAL PROPERTIES
    TAKAHASHI, A
    KURASAWA, S
    IKEDA, D
    OKAMI, Y
    TAKEUCHI, T
    [J]. JOURNAL OF ANTIBIOTICS, 1989, 42 (11) : 1556 - 1561
  • [7] ALTEMICIDIN, A NEW ACARICIDAL AND ANTITUMOR SUBSTANCE .2. STRUCTURE DETERMINATION
    TAKAHASHI, A
    IKEDA, D
    NAKAMURA, H
    NAGANAWA, H
    KURASAWA, S
    OKAMI, Y
    TAKEUCHI, T
    IITAKA, Y
    [J]. JOURNAL OF ANTIBIOTICS, 1989, 42 (11) : 1562 - 1566
  • [8] STRUCTURE DETERMINATION OF ALTEMICIDIN BY NMR SPECTROSCOPIC ANALYSIS
    TAKAHASHI, A
    NAGANAWA, H
    IKEDA, D
    OKAMI, Y
    [J]. TETRAHEDRON, 1991, 47 (22) : 3621 - 3632
  • [9] SYNTHESIS OF (S,S)-2-AMINO-3-PHENYLBUTYRIC ACID
    TSUCHIHASHI, G
    MITAMURA, S
    OGURA, K
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1979, 52 (07) : 2167 - 2168