A very-long-chain fatty acid (VLCFA) is a
fatty acid with 22 or more carbons. Their biosynthesis occurs in the
endoplasmic reticulum
The endoplasmic reticulum (ER) is, in essence, the transportation system of the eukaryotic cell, and has many other important functions such as protein folding. It is a type of organelle made up of two subunits – rough endoplasmic reticulum ( ...
. VLCFA's can represent up to a few percent of the total fatty acid content of a cell.
Unlike most fatty acids, VLCFAs are too long to be metabolized in the
mitochondria
A mitochondrion (; ) is an organelle found in the Cell (biology), cells of most Eukaryotes, such as animals, plants and Fungus, fungi. Mitochondria have a double lipid bilayer, membrane structure and use aerobic respiration to generate adenosi ...
, in the
endoplasmic reticulum
The endoplasmic reticulum (ER) is, in essence, the transportation system of the eukaryotic cell, and has many other important functions such as protein folding. It is a type of organelle made up of two subunits – rough endoplasmic reticulum ( ...
(ER) in plants and must be metabolized in
peroxisome
A peroxisome () is a membrane-bound organelle, a type of microbody, found in the cytoplasm of virtually all eukaryotic cells. Peroxisomes are oxidative organelles. Frequently, molecular oxygen serves as a co-substrate, from which hydrogen pero ...
s.
Certain peroxisomal disorders, such as
adrenoleukodystrophy and
Zellweger syndrome, can be associated with an accumulation of VLCFAs.
Enzymes that produce VLCFAs are the targets of
herbicide
Herbicides (, ), also commonly known as weedkillers, are substances used to control undesired plants, also known as weeds.EPA. February 201Pesticides Industry. Sales and Usage 2006 and 2007: Market Estimates. Summary in press releasMain page fo ...
s including
pyroxasulfone
Pyroxasulfone is a Herbicide#Timing_of_application, pre-emergence herbicide that inhibits the production of very long chain fatty acids in plants. The structure of the existing herbicide thiobencarb served as the basis for development but pyroxasul ...
.
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
Geddic acid, or tetratriacontanoic acid, is a 34-carbon-long carboxylic acid and saturated fatty acid. It occurs in cotton, carnauba, candelilla wax, and in ghedda wax (wild beeswax), from which its common name is derived.
See also
* List of ...
(C34), and the
odd-chain fatty acid ceroplastic acid
Ceroplastic acid (or pentatriacontanoic acid) is a saturated aliphatic carboxylic acid.
The name is derived from the Latin word ''cerotus'', which in turn was derived from the Ancient Greek word κηρός (keros), meaning beeswax or honeycomb, ...
(C35). Several monounsaturated VLCFAs are also known:
nervonic acid (Δ15-24:1),
ximenic acid (Δ17-26:1), and
lumequeic acid (Δ21-30:1).
See also
*
ACADVL
Very long-chain specific acyl-CoA dehydrogenase, mitochondrial (VLCAD) is an enzyme that in humans is encoded by the ACADVL gene.
Mutations in the ACADVL are associated with very long-chain acyl-coenzyme A dehydrogenase deficiency. The protein ...
*
SLC27A2
Very long-chain acyl-CoA synthetase is an enzyme that in humans is encoded by the ''SLC27A2'' gene.
The protein encoded by this gene is an isozyme of long-chain fatty-acid-coenzyme A ligase family. Although differing in substrate specificity, subc ...
*
SLC27A5
Bile acyl-CoA synthetase is an enzyme that in humans is encoded by the ''SLC27A5'' gene.
The protein encoded by this gene is an isozyme of very long-chain acyl-CoA synthetase (VLCS). It is capable of activating very long-chain fatty-acids contain ...
*
Cerotic acid, the fatty acid associated with adrenoleukodystrophy
References
Bibliography
*
Fatty acids
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