Design, modeling and synthesis of functionalized paromamine analogs

被引:34
作者
Hanessian, S [1 ]
Tremblay, M [1 ]
Kornienko, A [1 ]
Moitessier, N [1 ]
机构
[1] Univ Montreal, Dept Chem, Quebec City, PQ H3C 3J7, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
aminoglycoside; paromomycin; RNA; library; modeling;
D O I
10.1016/S0040-4020(01)00194-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Based on the published NMR structure of the antibiotic paromomycin complexed with the A-site of Escherichia coli 16S ribosomal RNA, a set of C-5 functionalized analogs of paromamine was designed and synthesized, incorporating cyclic and acyclic appendages and terminating with one or more ammonium groups. (C) 2001 Elsevier Science Ltd. Ah rights reserved.
引用
收藏
页码:3255 / 3265
页数:11
相关论文
共 48 条
  • [1] Probing the specificity of aminoglycoside ribosomal RNA interactions with designed synthetic analogs
    Alper, PB
    Hendrix, M
    Sears, P
    Wong, CH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (09) : 1965 - 1978
  • [2] Self-assembly of a water-soluble [2]rotaxane with carbohydrate stoppers
    Ashton, PR
    Everitt, SRL
    GomezLopez, M
    Jayaraman, N
    Stoddart, JF
    [J]. TETRAHEDRON LETTERS, 1997, 38 (32) : 5691 - 5694
  • [3] ATWELL GJ, 1984, SYNTHESIS-STUTTGART, P1032
  • [4] Preparations of two pivotal intermediates for the synthesis of 1-beta-methyl carbapenem antibiotics
    Berks, AH
    [J]. TETRAHEDRON, 1996, 52 (02) : 331 - 375
  • [5] NEW HYDROGEN-BOND POTENTIALS FOR USE IN DETERMINING ENERGETICALLY FAVORABLE BINDING-SITES ON MOLECULES OF KNOWN STRUCTURE
    BOOBBYER, DNA
    GOODFORD, PJ
    MCWHINNIE, PM
    WADE, RC
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (05) : 1083 - 1094
  • [6] Functional insights from the structure of the 30S ribosomal subunit and its interactions with antibiotics
    Carter, AP
    Clemons, WM
    Brodersen, DE
    Morgan-Warren, RJ
    Wimberly, BT
    Ramakrishnan, V
    [J]. NATURE, 2000, 407 (6802) : 340 - 348
  • [7] New directions in antibacterial research
    Chu, DTW
    Plattner, JJ
    Katz, L
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (20) : 3853 - 3874
  • [8] INACTIVATION OF ANTIBIOTICS AND THE DISSEMINATION OF RESISTANCE GENES
    DAVIES, J
    [J]. SCIENCE, 1994, 264 (5157) : 375 - 382
  • [9] Efficient synthesis of neomycin B related aminoglycosides
    Ding, YL
    Swayze, EE
    Hofstadler, SA
    Griffey, RH
    [J]. TETRAHEDRON LETTERS, 2000, 41 (21) : 4049 - 4052
  • [10] The aminoglycosides
    Edson, RS
    Terrell, CL
    [J]. MAYO CLINIC PROCEEDINGS, 1999, 74 (05) : 519 - 528