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Structure determination of mycolic acids by using charge remote fragmentation
A Savagnac1, H Aurelle, C Casas
1Centre de Recherche de Biochimie et Génétique Cellulaires C.N.R.S., Toulouse, France.
Chemistry and Physics of Lipids
|July 1, 1989
Summary
Collision-induced remote site fragmentation is a powerful tool for fatty acid structural determination. This method identified a novel tri-unsaturated mycolic acid in Mycobacterium fallax.
Area of Science:
- Analytical Chemistry
- Organic Chemistry
- Biochemistry
Background:
- Collision-induced remote site fragmentation of carboxylate anions is crucial for fatty acid structural analysis.
- Direct analysis of Corynebacterium diphtheriae mycolic acids is possible, but mycobacterial mycolic acids require preliminary chemical modification.
Purpose of the Study:
- To develop and apply an improved analytical method for the structural determination of complex mycolic acids.
- To characterize novel mycolic acid structures from mycobacteria.
Main Methods:
- Mycolic acids were chemically cleaved via oxidation to beta-keto esters, followed by a retro-Claisen reaction.
- Fatty acids were converted to pentafluorobenzyl derivatives for analysis.
- High-pressure ion source with negative ion mode and helium collision-induced dissociation (CID) were employed for gas-phase carboxylate anion fragmentation.
Main Results:
- The method successfully characterized M3-mycolic acids from Mycobacterium fallax.
- A new tri-unsaturated mycolic acid was identified, featuring specific spacing between double bonds.
- The fragmentation patterns provided detailed structural information, including the location of unsaturation.
Conclusions:
- The developed method enhances the structural elucidation of mycolic acids from mycobacteria.
- This technique is valuable for identifying novel fatty acid structures and understanding microbial lipid diversity.
- Further application of this method can aid in the study of complex lipid structures in various biological systems.