Tauramamide, a lipopeptide antibiotic produced in culture by Brevibacillus laterosporus isolated from a marine habitat: structure elucidation and synthesis.
Tauramamide (1), a new lipopeptide antibiotic, is produced by cultures of the marine bacterial isolate Brevibacillus laterosporus PNG276 obtained from Papua New Guinea. Tauramamide was isolated as its methyl and ethyl esters 2 and 3, whose structures were elucidated by analysis of NMR, MS, and chemical degradation data. A total synthesis of tauramamide (1) and tauramamide ethyl ester (3) confirmed the structure proposed from spectroscopic analysis and provided the natural product for antimicrobial testing. Tauramamide (1) and ethyl ester 3 show potent and relatively selective inhibition of pathogenic Enterococcus sp.
Desjardine
Kelsey
K
Department of Chemistry, University of British Columbia, Vancouver, British Columbia, Canada.
Pereira
Alban
A
Wright
Helen
H
Matainaho
Teatulohi
T
Kelly
Michael
M
Andersen
Raymond J
RJ
D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D001407:Bacillus / Q000737:chemistry*; D016983:Enterococcus / Q000187:drug effects*; D055666:Lipopeptides; D008074:Lipoproteins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D008386:Marine Biology; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D010219:Papua New Guinea
D000900:Anti-Bacterial Agents; D055666:Lipopeptides; D008074:Lipoproteins; C526654:tauramamide