Recent Progress in the Synthesis of Naturally Occurring Siderophores

被引:9
作者
Garzon-Posse, Fabian [1 ,3 ]
Quevedo-Acosta, Yovanny [1 ,2 ]
Mahecha-Mahecha, Camilo [1 ]
Acosta-Guzman, Paola [1 ]
机构
[1] Univ Andes, Lab Organ Synth, Bio & Organocatalysis Chem Dept, Cra 1 18A-12 Q 305, Bogota 111711, Colombia
[2] Univ Estadual Campinas, Inst Chem, Rua Monteiro Lobato 270, BR-13083862 Campinas, SP, Brazil
[3] Univ Nacl Colombia, Lab Nat Prod, Carrera 45 26-85, Bogota, Colombia
关键词
Siderophores; Total synthesis; Iron chelators; STRUCTURE ELUCIDATION; STEREOCHEMICAL ASSIGNMENT; ABSOLUTE-CONFIGURATION; 2'-DEOXYMUGINEIC ACID; BACTERIAL SIDEROPHORE; BIOLOGICAL-ACTIVITY; VIBRIO-ANGUILLARUM; STRUCTURE REVISION; CHEMICAL-SYNTHESIS; HYDROXAMIC ACIDS;
D O I
10.1002/ejoc.201901257
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Iron is an indispensable element for the development of almost all living things, and its acquisition is a key process for organisms. However, the low solubility of Fe3+ in aqueous systems causes its reduced bioavailability. Thus, organisms confronted with low iron availability have developed several iron scavenging strategies, and one of these ways is to use low molecular-weight organic molecules, which are specific ferric ion chelators called siderophores. These compounds exhibit an extremely high affinity and specificity for Fe3+ and are produced and secreted by bacteria, fungi, and plants. Recently, siderophores have attracted much attention due to their applications in areas such as microbial ecology, specific crop production, detoxification of heavy metal-contaminated samples, biodetection of metals, and the selective delivery of antibiotics to resistant bacterial strains. Nevertheless, the limited supply of these natural products has been an obstacle that needs to be overcome. This review provides an overview of the contemporary developments in the total synthesis of naturally occurring siderophores during the last two decades.
引用
收藏
页码:7747 / 7769
页数:23
相关论文
共 83 条
  • [1] CHARACTERIZATION OF ANGUIBACTIN, A NOVEL SIDEROPHORE FROM VIBRIO-ANGUILLARUM 775(PJM1)
    ACTIS, LA
    FISH, W
    CROSA, JH
    KELLERMAN, K
    ELLENBERGER, SR
    HAUSER, FM
    SANDERSLOEHR, J
    [J]. JOURNAL OF BACTERIOLOGY, 1986, 167 (01) : 57 - 65
  • [2] SYNTHESIS AND BIOLOGICAL-ACTIVITY OF PYOCHELIN, A SIDEROPHORE OF PSEUDOMONAS-AERUGINOSA
    ANKENBAUER, RG
    TOYOKUNI, T
    STALEY, A
    RINEHART, KL
    COX, CD
    [J]. JOURNAL OF BACTERIOLOGY, 1988, 170 (11) : 5344 - 5351
  • [3] [Anonymous], 2007, ANGEW CHEM
  • [4] Petrobactin, a photoreactive siderophore produced by the oil-degrading marine bacterium Marinobacter hydrocarbonoclasticus
    Barbeau, K
    Zhang, GP
    Live, DH
    Butler, A
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (03) : 378 - 379
  • [5] A BIOSENSOR FOR FERRIC ION
    BARRERO, JM
    MORENOBONDI, MC
    PEREZCONDE, MC
    CAMARA, C
    [J]. TALANTA, 1993, 40 (11) : 1619 - 1623
  • [6] Synthesis of heterobactins A and B and Nocardia heterobactin
    Bergeron, Raymond J.
    Singh, Shailendra
    Bharti, Neelam
    [J]. TETRAHEDRON, 2011, 67 (18) : 3163 - 3169
  • [7] Total synthesis and structure revision of petrobactin
    Bergeron, RJ
    Huang, GF
    Smith, RE
    Bharti, N
    McManis, JS
    Butler, A
    [J]. TETRAHEDRON, 2003, 59 (11) : 2007 - 2014
  • [8] Bacterial siderophore mimicking iron complexes as DNA targeting antimicrobials
    Boda, Sunil Kumar
    Pandit, Subhendu
    Garai, Aditya
    Pal, Debnath
    Basu, Bikramjit
    [J]. RSC ADVANCES, 2016, 6 (45): : 39245 - 39260
  • [9] Enhanced phytoextraction of an agricultural Cr- and Pb-contaminated soil by bioaugmentation with siderophore-producing bacteria
    Braud, Armelle
    Jezequel, Karine
    Bazot, Stephane
    Lebeau, Thierry
    [J]. CHEMOSPHERE, 2009, 74 (02) : 280 - 286
  • [10] Sideromycins: tools and antibiotics
    Braun, Volkmar
    Pramanik, Avijit
    Gwinner, Thomas
    Koeberle, Martin
    Bohn, Erwin
    [J]. BIOMETALS, 2009, 22 (01) : 3 - 13