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.