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'Mycolic acids' are long fatty acids found in the cell walls of the mycolata taxon, a group of bacteria which includes ''Mycobacterium tuberculosis'', the causative agent of the disease tuberculosis. They form the major component of the cell wall of mycolata species. Despite their name, mycolic acids have no biological link to fungi; the name arises from the filamentous appearance their presence gives mycolata under high magnification. The presence of mycolic acids in the cell wall also gives mycolata a distinct gross morphological trait known as "cording." Mycolic acids were first isolated by Stodola ''et al.'' in 1938 from an extract of ''M. tuberculosis''.
Mycolic acids are comprised of a shorter beta-hydroxy chain with a longer alpha-alkyl side chain. Each molecule contains between 60 and 90 carbon atoms. The exact number of carbons varies by species and can be used as an identification aid. Most mycolic acids also contain various functional groups.

Contents

Mycolic Acids of ''M. tuberculosis''

Mycolic Acids of ''Rhodococcus'' sp.

Further reading

Mycolic Acids of ''M. tuberculosis''

''M. tuberculosis'' produces three main types of mycolic acids: alpha-, methoxy-, and keto-. Alpha-mycolic acids comprise at least 70% of the mycolic acids present in the organism and contain several cyclopropane rings. Methoxy-mycolic acids, which contain several methoxy groups, comprise between 10 and 15% of the mycolic acids in the organism. The remaining 10 to 15% of the mycolic acids are keto-mycolic acids, which contain several ketone groups.
The presence of mycolic acids gives ''M. tuberculosis'' many of its medically frustrating characteristics. They lend the organism increased resistance to chemical damage and dehydration and prevent the effective activity of hydrophobic antibiotics. Additionally, the mycolic acids allow the bacterium to grow readily inside macrophages, effectively hiding it from the host's immune system.
The exact structure of mycolic acids appears to be closely linked to the virility of the organism, as modification of the functional groups of the molecule can lead to an attenuation of growth ''in vivo''. Additionally, individuals with mutations in genes responsible for mycolic acid synthesis exhibit altered cording.
'Figure:' An example of a mycolic acid from ''Mycobacterium tuberculosis''

Mycolic Acids of ''Rhodococcus'' sp.

The mycolic acids of members of the genus ''Rhodococcus'', another member of the mycolata taxon, differ in several ways from those of ''M. tuberculosis''. They contain no functional groups, but instead may have several unsaturated bonds. Two different profiles of ''Rhodococcus'' mycolic acids exist. The first has between 28 and 46 carbon atoms with either 0 or 1 unsaturated bond. The second has between 34 and 54 carbon atoms with between 0 and 4 unsaturated bonds. Sutcliffe (1998) has proposed that they are linked to the rest of the cell wall by arabinogalactan molecules.

Further reading

★ Barry ''et al.'' (1998). "Mycolic acids: structure, biosynthesis, and physiological functions." Prog. Lipid Res. '37'(3): 143-79.

★ Nishiuchi, Baba, and Yano (1999). "Mycolic acids from ''Rhodococcus'', ''Gordonia'', and ''Dietzia''." J. Microbiol. Methods '40': 1-9.

★ Sutcliffe (1998). "Cell envelope composition and organization in the genus ''Rhodococcus''." Antonie van Leeuwenhoek '74': 49-58.

★ Takayama, Wang, and Besra (2005). "Pathway to synthesis and processing of mycolic acids in ''Mycobacterium tuberculosis''." Clin. Microbiol. Rev. '18'(1): 81-101.