Synthesis and structure of mycolactone E isolated from frog mycobacterium.
The structure of mycolactone E, isolated from the frog pathogen Mycobacterium liflandii, was established via organic synthesis. Within the mycolactone family of metabolites, a structural variation has been seen only at the unsaturated fatty acid moiety thus far, and mycolactone E follows this observation. Interestingly, the absolute configuration of its unsaturated fatty acid matches that of the mycolactones from human mycobacteria, rather than the structurally more closely related mycolactone F from fish mycobacteria.
Aubry
Sylvain
S
Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, USA.
Lee
Richard E
RE
Mahrous
Engy A
EA
Small
Pam L C
PL
Beachboard
Dia
D
Kishi
Yoshito
Y
D000818:Animals; D001001:Anura / Q000382:microbiology*; D005231:Fatty Acids, Unsaturated / Q000138:chemical synthesis* / Q000737:chemistry* / Q000302:isolation & purification; D006801:Humans; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry* / Q000302:isolation & purification; D009682:Magnetic Resonance Spectroscopy; D009161:Mycobacterium / Q000737:chemistry*; D053719:Tandem Mass Spectrometry
D005231:Fatty Acids, Unsaturated; D007783:Lactones; C552499:mycolactone E