THE TOTAL SYNTHESIS OF NANNOCHELIN - A NOVEL CINNAMOYL HYDROXAMATE-CONTAINING SIDEROPHORE

被引:35
作者
BERGERON, RJ
PHANSTIEL, O
机构
[1] Department of Medicinal Chemistry, University of Florida, J. Hillis Miller Health Center, Gainesville
关键词
D O I
10.1021/jo00052a030
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The total synthesis of nannochelin A, a siderophore isolated from Nannocystis exedens, is described. The key transformation involves the tandem oxidation-acylation of the N(epsilon)-amino group of N(alpha)-BOC-L-lysine methyl ester prior to coupling with the external carboxyls of citric acid.
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页码:7140 / 7143
页数:4
相关论文
共 18 条
  • [1] ASKOY M, 1985, HYPERTRANSFUSION IRO, P80
  • [2] Bergeron R.J., 1991, CRC HDB MICROBIAL IR, V1st ed., P271
  • [3] THE TOTAL SYNTHESIS OF ALCALIGIN
    BERGERON, RJ
    MCMANIS, JS
    PERUMAL, PT
    ALGEE, SE
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (19) : 5560 - 5563
  • [4] THE TOTAL SYNTHESIS OF BISUCABERIN
    BERGERON, RJ
    MCMANIS, JS
    [J]. TETRAHEDRON, 1989, 45 (16) : 4939 - 4944
  • [5] SYNTHESIS AND BIOLOGICAL EVALUATION OF HYDROXAMATE-BASED IRON CHELATORS
    BERGERON, RJ
    WIEGAND, J
    MCMANIS, JS
    PERUMAL, PT
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (11) : 3182 - 3187
  • [6] CHELATION THERAPY IN BETA-THALASSEMIA MAJOR .1. INTRAVENOUS AND SUBCUTANEOUS DEFEROXAMINE
    GRAZIANO, JH
    MARKENSON, A
    MILLER, DR
    CHANG, H
    BESTAK, M
    MEYERS, P
    PISCIOTTO, P
    RIFKIND, A
    [J]. JOURNAL OF PEDIATRICS, 1978, 92 (04) : 648 - 652
  • [7] ANTIBIOTICS FROM GLIDING BACTERIA .46. NANNOCHELIN-A, NANNOCHELIN-B AND NANNOCHELIN-C, NEW IRON-CHELATING COMPOUNDS FROM NANNOCYSTIS-EXEDENS (MYXOBACTERIA) PRODUCTION, ISOLATION, PHYSICOCHEMICAL AND BIOLOGICAL PROPERTIES
    KUNZE, B
    TROWITZSCHKIENAST, W
    HOFLE, G
    REICHENBACH, H
    [J]. JOURNAL OF ANTIBIOTICS, 1992, 45 (02) : 147 - 150
  • [8] NATURAL FERRIC IONOPHORES - TOTAL SYNTHESIS OF SCHIZOKINEN, SCHIZOKINEN-A, AND ARTHROBACTIN
    LEE, BH
    MILLER, MJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (01) : 24 - 31
  • [9] MICROBIAL IRON CHELATORS - TOTAL SYNTHESIS OF AEROBACTIN AND ITS CONSTITUENT AMINO-ACID, N6-ACETYL-N6-HYDROXYLYSINE
    MAURER, PJ
    MILLER, MJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (11) : 3096 - 3101
  • [10] SYNTHESIS OF SCHIZOKINEN, HOMOSCHIZOKINEN, ITS IMIDE AND THE DETECTION OF IMIDE WITH C-13-NMR-SPECTROSCOPY
    MILEWSKA, MJ
    CHIMIAK, A
    GLOWACKI, Z
    [J]. JOURNAL FUR PRAKTISCHE CHEMIE, 1987, 329 (03): : 447 - 456