A very-long-chain fatty acid (VLCFA) is a
fatty acid
In chemistry, in particular in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated and unsaturated compounds#Organic chemistry, saturated or unsaturated. Most naturally occurring fatty acids have an ...
with 22 or more carbons. Their biosynthesis occurs in the
endoplasmic reticulum
The endoplasmic reticulum (ER) is a part of a transportation system of the eukaryote, eukaryotic cell, and has many other important functions such as protein folding. The word endoplasmic means "within the cytoplasm", and reticulum is Latin for ...
. 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 cells of most eukaryotes, such as animals, plants and fungi. Mitochondria have a double membrane structure and use aerobic respiration to generate adenosine triphosphate (ATP), which is us ...
, in the
endoplasmic reticulum
The endoplasmic reticulum (ER) is a part of a transportation system of the eukaryote, eukaryotic cell, and has many other important functions such as protein folding. The word endoplasmic means "within the cytoplasm", and reticulum is Latin for ...
(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 perox ...
s.
Certain peroxisomal disorders, such as
adrenoleukodystrophy
Adrenoleukodystrophy (ALD) is a genetic disorder, disease linked to the X chromosome. It is a result of fatty acid buildup caused by failure of peroxisome#Metabolic functions, peroxisomal fatty acid beta oxidation which results in the accumulation ...
and
Zellweger syndrome
Zellweger syndrome is a rare congenital disorder characterized by the reduction or absence of functional peroxisomes in the cells of an individual. It is one of a family of disorders called Zellweger spectrum disorders which are leukodystrophy, l ...
, can be associated with an accumulation of VLCFAs.
Enzymes that produce VLCFAs are the targets of
herbicide
Herbicides (, ), also commonly known as weed killers, 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 f ...
s including
pyroxasulfone.
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).
See also
*
ACADVL
*
SLC27A2
*
SLC27A5
*
Cerotic acid, the fatty acid associated with adrenoleukodystrophy
References
Bibliography
*
Fatty acids
{{OrganicAcid-stub