Isolation and structural characterization of a new non-phosphorylated lipoamino acid from Mycobacterium phlei.
A new non-phosphorylated lipoamino acid was extracted from Mycobacterium phlei, strain IST. It is particularly sensitive to alkaline hydrolysis, and contains a lysine residue joined to a 1,2-diglyceride via an ester linkage. The FAB-positive mass spectrum shows the presence of various molecular species of which the most abundant contains a palmitic and a tuberculostearic acid residue. An analogue of this lipid was synthesized, 1,2-dipalmitoyl 3-lysyl glycerol. Both its chromatographic behavior (TLC), and the decomposition pathways of the MH+ ions, studied by FAB MS and MIKE spectroscopy, were identical to the natural product.
Lerouge
P
P
Centre de Recherche de Biochimie et Génétique cellularie, Toulouse, France.
Lebas
M H
MH
Agapakis-Caussé
C
C
Promé
J C
JC
D000596:Amino Acids / Q000138:chemical synthesis / Q000302:isolation & purification*; D002849:Chromatography, Gas; D002855:Chromatography, Thin Layer; D008055:Lipids / Q000138:chemical synthesis / Q000302:isolation & purification*; D013058:Mass Spectrometry; D015394:Molecular Structure; D009161:Mycobacterium / Q000032:analysis*; D009168:Mycobacterium phlei / Q000032:analysis*
D000596:Amino Acids; D008055:Lipids