Chemistry:Very long chain fatty acid

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Short description: Fatty acid with 22 or more carbons

A very-long-chain fatty acid (VLCFA) is a fatty acid with 22 or more carbons. 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]

See also

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. http://www.x-ald.nl/biochemistry-genetics/vlcfa/. 
  4. ↑ "Very long-chain acyl-CoA dehydrogenase deficiency". Genetics Home Reference, National Institutes of Health. http://ghr.nlm.nih.gov/condition/very-long-chain-acyl-coa-dehydrogenase-deficiency. 
  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. 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. doi:10.1073/pnas.0404600101. PMID 15277688. Bibcode: 2004PNAS..10111903T. 
  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. 




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