A progressive synthetic strategy for class B synergimycins

被引:6
作者
Robinson, JL [1 ]
Taylor, RE [1 ]
Liotta, LA [1 ]
Bolla, ML [1 ]
Azevedo, EV [1 ]
Medina, I [1 ]
McAlpine, SR [1 ]
机构
[1] San Diego State Univ, Dept Chem, San Diego, CA 92182 USA
关键词
class B; synergimycin; antibiotic; virginiamycin;
D O I
10.1016/j.tetlet.2004.01.048
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Described are the syntheses of four macrocyclic peptides that are the core structure of class B synergimycins, and the synthesis of a final class B derivative. Our synthetic route to these synergimycin derivatives allows the incorporation of amino acid substitutions Lit all points in the macrocycle, leading to structurally diverse class B analogs. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2147 / 2150
页数:4
相关论文
共 16 条
[1]   SOLUTION CONFORMATION OF VIRGINIAMYCINS (STAPHYLOMYCINS) [J].
ANTEUNIS, MJO ;
CALLENS, REA ;
TAVERNIER, DK .
EUROPEAN JOURNAL OF BIOCHEMISTRY, 1975, 58 (02) :259-268
[2]  
ANTEUNIS MJO, 1988, B SOC CHIM BELG, V97, P281
[3]  
ANTEUNIS MJO, 1988, B SOC CHIM BELG, V97, P135
[4]   Novel antibiotics: Macrocyclic peptides designed to trap Holliday junctions [J].
Bolla, ML ;
Azevedo, EV ;
Smith, JM ;
Taylor, RE ;
Ranjit, DK ;
Segall, AM ;
McAlpine, SR .
ORGANIC LETTERS, 2003, 5 (02) :109-112
[5]   Specific inhibition of 50S ribosomal subunit formation in Staphylococcus aureus cells by 16-membered macrolide, lincosamide, and streptogramin B antibiotics [J].
Champney, WS ;
Tober, CL .
CURRENT MICROBIOLOGY, 2000, 41 (02) :126-135
[7]   Mutation in 23S rRNA responsible for resistance to 16-membered macrolides and streptogramins in Streptococcus pneumoniae [J].
Depardieu, F ;
Courvalin, P .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 2001, 45 (01) :319-323
[8]  
DIGIAMBATTISTA M, 1990, B SOC CHIM BELG, V99, P195
[9]  
DIGIAMBATTISTA M, 1984, J BIOL CHEM, V259, P6334
[10]  
ENNIS HL, 1965, J BACTERIOL, V90, P1102