Very long chain fatty acid

In the field of biology, very-long-chain fatty acid (VLCFA) is a fatty acid with 22 or more carbons. In chemistry, these are more commonly knowns as wax acids, a subgroup of saturated unbranched alkanoic acids. The frontier between fatty acids (strictly defined) and wax acids is fluid.

Biological importance

Their biosynthesis occurs in the endoplasmic reticulum. ^[1] VLCFA's can represent up to a few percent of the total fatty acid content of a cell. ^[2]

Unlike most fatty acids, VLCFAs are too long to be metabolized in the mitochondria, in the endoplasmic reticulum (ER) in plants and must be metabolized in peroxisomes.

Certain peroxisomal disorders, such as adrenoleukodystrophy and Zellweger syndrome, can be associated with an accumulation of VLCFAs. ^{[3] [4]} Enzymes that produce VLCFAs are the targets of herbicides including pyroxasulfone. ^{[5] [6]}

Major VLCFAs

Some of the more common saturated VLCFAs: lignoceric acid (C24), cerotic acid (C26), montanic acid (C28), melissic acid (C30), lacceroic acid (C32), ghedoic acid (C34), and the odd-chain fatty acid ceroplastic acid (C35). Several monounsaturated VLCFAs are also known: nervonic acid (Δ15-24:1), ximenic acid (Δ17-26:1), and lumequeic acid (Δ21-30:1). ^[7]

The edge case wax acid is behenic acid (C-22).

See also

• ACADVL
• SLC27A2
• SLC27A5
• Cerotic acid, the fatty acid associated with adrenoleukodystrophy

References

1. Jakobsson, Andreas; Westerberg, Rolf; Jacobsson, Anders "Fatty acid elongases in mammals: their regulation and roles in metabolism" Progress in Lipid Research 2006, volume 45, pp. 237–249. doi : 10.1016/j.plipres.2006.01.004
2. "Very-long-chain fatty acids from the animal and plant kingdoms" Rezanka, Tomas Progress in Lipid Research 1989, volume 28, pp. 147–87. doi : 10.1016/0163-7827(89)90011-8
3. Kemp, Stephan and Watkins, Paul. "Very long-chain fatty acids". X-ald Database. Retrieved 5 January 2013.
4. "Very long-chain acyl-CoA dehydrogenase deficiency". Genetics Home Reference, National Institutes of Health. Retrieved 5 January 2013.
5. Nakatani, Masao; Yamaji, Yoshihiro; Honda, Hisashi; Uchida, Yukio (2016). "Development of the novel pre-emergence herbicide pyroxasulfone". Journal of Pesticide Science. 41 (3): 107–112. doi: 10.1584/jpestics.J16-05 . PMC   6140635 . PMID   30363083.
6. Trenkamp, S.; Martin, W.; Tietjen, K. (10 August 2004). "Specific and differential inhibition of very-long-chain fatty acid elongases from Arabidopsis thaliana by different herbicides". Proceedings of the National Academy of Sciences. 101 (32): 11903–11908. Bibcode:2004PNAS..10111903T. doi: 10.1073/pnas.0404600101 . PMC   511072 . PMID   15277688.
7. Řezanka, Tomáš; Sigler, Karel (2009). "Odd-Numbered Very-Long-Chain Fatty Acids from the Microbial, Animal and Plant Kingdoms". Progress in Lipid Research. 48 (3–4): 206–238. doi:10.1016/j.plipres.2009.03.003. PMID   19336244.

Bibliography

• Moser, H. W.; Moser, A. B.; Frayer, K. K.; Chen, W.; Schulman, J. D.; O'Neill, B. P.; Kishimoto, Y. (1981). "Adrenoleukodystrophy: Increased plasma content of saturated very long chain fatty acids". Neurology . 31 (10): 1241–9. doi: 10.1212/WNL.31.10.1241 . ISSN   0028-3878. PMID   7202134.