Solid-Phase Synthesis of Lysobactin (Katanosin B): Insights into Structure and Function

被引:10
|
作者
Hall, Edward A. [1 ]
Kuru, Erkin [1 ]
VanNieuwenhze, Michael S. [1 ]
机构
[1] Indiana Univ, Dept Chem, Bloomington, IN 47405 USA
基金
美国国家卫生研究院;
关键词
COUPLING REAGENT; REMARKABLE RESISTANCE; DEPBT;
D O I
10.1021/ol300926d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The solid phase synthesis of the cyclic depsipeptide antibiotic lysobactin is described. The natural product was synthesized via a linear approach using mostly an Fmoc-strategy solid phase peptide synthesis (SPPS) with a single purification. A lysobactin analog has also been synthesized displaying nanomolar membrane disruption activity not seen with the natural product.
引用
收藏
页码:2730 / 2733
页数:4
相关论文
共 50 条
  • [1] Structure and total synthesis of lysobactin (katanosin B)
    von Nussbaum, Franz
    Anlauf, Sonja
    Benet-Buchholz, Jordi
    Haebich, Dieter
    Koebberling, Johannes
    Musza, Laszlo
    Telser, Joachim
    Ruebsamen-Waigmann, Helga
    Brunner, Nina A.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (12) : 2039 - 2042
  • [2] Total solid-phase synthesis of depsipeptide antibiotic Katanosin B.
    Stawikowska, R.
    Stawikowski, M.
    Cudic, P.
    BIOPOLYMERS, 2007, 88 (04) : 569 - 569
  • [3] Progress toward Total Solid-Phase Synthesis of Depsipeptide Antibiotic Katanosin B
    Stawikowska, Roma
    Stawikowski, Maciej
    Cudic, Predrag
    PEPTIDES FOR YOUTH, 2009, 611 : 385 - 386
  • [4] TOTAL Fmoc SOLID-PHASE SYNTHESIS OF NATURALLY OCCURRING DEPSIPEPTIDE ANTIBIOTIC KATANOSIN B
    Cudic, M.
    Bionda, N.
    Binetti, D.
    Cudic, P.
    BIOPOLYMERS, 2009, 92 (04) : 365 - 365
  • [5] Solid phase synthesis of lysobactin and analog studies
    Hall, Edward A.
    VanNieuwenhze, Michael S.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
  • [6] Solid-phase total synthesis and structure proof of callipeltin B
    Krishnamoorthy, Ravi
    Vazquez-Serrano, Leslie D.
    Turk, Jeffrey A.
    Kowalski, Jennifer A.
    Benson, Alan G.
    Breaux, Nneka T.
    Lipton, Mark A.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (48) : 15392 - 15393
  • [7] Solid-phase synthesis
    Andreu, David
    CHEMICAL & ENGINEERING NEWS, 2007, 85 (03) : 11 - 11
  • [8] SOLID-PHASE SYNTHESIS
    NECKERS, DC
    JOURNAL OF CHEMICAL EDUCATION, 1975, 52 (11) : 695 - 702
  • [9] Solid-phase synthesis
    1600, (11):
  • [10] SOLID-PHASE SYNTHESIS
    NECKERS, DC
    CHEMTECH, 1978, 8 (02) : 108 - 116