|Formula||C 6H14 N4O 2|
Arginine (abbreviated as Arg or R) encoded by the codons CGU, CGC,
CGA, CGG, AGA, and AGG is an α-amino acid that is used in the
biosynthesis of proteins. It contains an α-amino group (which is in
the protonated −NH3+ form under biological conditions), an
α-carboxylic acid group (which is in the deprotonated −COO− form
under biological conditions), and a side chain of a 3-carbon
aliphatic straight chain capped by a complex guanidinium,
classifying it as a charged (at physiological pH), aliphatic amino
acid. Arginine is classified as a semiessential or conditionally
essential amino acid, depending on the developmental stage and
health status of the individual. Preterm infants are unable to
synthesize or create arginine internally, making the amino acid
nutritionally essential for them. Most healthy people do not
need to supplement with arginine because their body produces
sufficient amounts. Arginine was first isolated from a lupin
seedling extract in 1886 by the German chemist Ernst Schultze.
A conditionally essential amino acid is one that may be required
depending on the health status or life cycle of the individual.
Arginine is one such conditionally essential amino acid. The
biosynthetic pathway, however, does not produce sufficient
arginine, and some must still be consumed through diet.[citation
needed] Individuals with poor nutrition or certain physical
conditions may be advised to increase their intake of foods
containing arginine. Arginine is found in a wide variety of foods,
dairy products (e.g., cottage cheese, ricotta, milk, yogurt, whey
protein drinks), beef, pork (e.g., bacon, ham), gelatin, poultry
(e.g. chicken and turkey light meat), wild game (e.g. pheasant,
quail), seafood (e.g., halibut, lobster, salmon, shrimp, snails,
wheat germ and flour, lupins, buckwheat, granola, oatmeal, peanuts,
nuts (coconut, pecans, cashews, walnuts, almonds, Brazil nuts,
hazelnuts, pinenuts), seeds (hemp, pumpkin, sesame, sunflower),
chickpeas, cooked soybeans, Phalaris canariensis (canaryseed or
Arginine is synthesized from citrulline in arginine and proline
metabolism by the sequential action of the cytosolic enzymes
argininosuccinate synthetase (ASS) and argininosuccinate lyase
(ASL). In terms of energy, this is costly, as the synthesis of each
molecule of argininosuccinate requires hydrolysis of adenosine
triphosphate (ATP) to adenosine monophosphate (AMP), i.e., two ATP
equivalents. In essence, taking an excess of arginine gives more
energy by saving ATPs that can be used elsewhere.
Citrulline can be derived from multiple sources:
- from arginine via nitric oxide synthase (NOS)
- from ornithine via catabolism of proline or glutamine/glutamate
- from asymmetric dimethylarginine (ADMA) via DDAH
The pathways linking arginine, glutamine, and proline are
bidirectional. Thus, the net utilization or production of these
amino acids is highly dependent on cell type and developmental
On a whole-body basis, synthesis of arginine occurs principally via
the intestinal–renal axis, wherein epithelial cells of the small
intestine, which produce citrulline primarily from glutamine and
glutamate, collaborate with the proximal tubule cells of the
kidney, which extract citrulline from the circulation and convert
it to arginine, which is returned to the circulation. As a
consequence, impairment of small bowel or renal function can reduce
endogenous arginine synthesis, thereby increasing the dietary
Synthesis of arginine from citrulline also occurs at a low level in
many other cells, and cellular capacity for arginine synthesis can
be markedly increased under circumstances that also induce iNOS.
Thus, citrulline, a coproduct of the NOS-catalyzed reaction, can be
recycled to arginine in a pathway known as the citrulline-NO or
arginine-citrulline pathway. This is demonstrated by the fact that,
in many cell types, citrulline can substitute for arginine to some
degree in supporting NO synthesis. However, recycling is not
quantitative because citrulline accumulates along with nitrate and
nitrite, the stable end-products of NO, in NO-producing cells.
Arginine plays an important role in cell division, the healing of
wounds, removing ammonia from the body, immune function, and the
release of hormones.
The roles of arginine include:
Precursor for the synthesis of nitric oxide (NO) Non-L-arginine
derived NO can be generated by the nitrate-nitrite-nitric oxide
pathway that is monitored through saliva testing.
Reduces healing time of injuries (particularly bone)
Quickens repair time of damaged tissue
Helps decrease blood pressure in clinical hypertensive subjects
NO-mediated decrease in blood pressure is influenced by both the
L-arginine-dependent nitric oxide synthase pathway and
non-L-arginine or alternative pathway through nitrate-rich foods
such as beets and spinach.
The distributing basics of the moderate structure found in
geometry, charge distribution, and ability to form multiple H-bonds
make arginine ideal for binding negatively charged groups. For this
reason, arginine prefers to be on the outside of the proteins,
where it can interact with the polar environment.
Incorporated in proteins, arginine can also be converted to
citrulline by PAD enzymes. In addition, arginine can be methylated
by protein methyltransferases.
Arginine is the immediate precursor of nitric oxide (NO), urea,
ornithine, and agmatine; is necessary for the synthesis of
creatine; and can also be used for the synthesis of polyamines
(mainly through ornithine and to a lesser degree through agmatine),
citrulline, and glutamate. As a precursor of nitric oxide, arginine
may have a role in the treatment of some conditions where
vasodilation is required. The presence of asymmetric
dimethylarginine (ADMA), a close relative, inhibits the nitric
oxide reaction; therefore, ADMA is considered a marker for vascular
disease, just as L-arginine is considered a sign of a healthy
Treatment of dentin hypersensitivity
Arginine (8%) in dental products (e.g., toothpaste) provides
effective relief from sensitive teeth by depositing a dentin-like
mineral, containing calcium and phosphate, within the dentin
tubules and in a protective layer on the dentin surface.
Treatment of herpes simplex virus
An unproven claim is that a low ratio of arginine to lysine may be
of benefit in the treatment of herpes simplex virus. For more
information, refer to Herpes – Treatment also see journal article.
L-arginine is generally recognized as safe (GRAS-status) at intakes
of up to 20 g/d.
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