L-arginine

L-アルギニン

関

arginine

WordNet

1. the 12th letter of the Roman alphabet (同)l
2. a bitter tasting amino acid found in proteins and necessary for nutrition; its absence from the diet leads to a reduced production of spermatozoa

PrepTutorEJDIC

1. lira(イタリアの貨幣単位リラ)
2. liter[s]

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/10/13 16:27:07」(JST)

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Arginine
Other names 2-Amino-5-guanidinopentanoic acid
Identifiers
CAS number	7200-25-1 N, 157-06-2 R Y, 74-79-3 S Y
PubChem	232, 71070 R, 6322 S
ChemSpider	227 Y, 64224 R Y, 6082 S Y
UNII	94ZLA3W45F Y
EC number	230-571-3
DrugBank	DB00125
KEGG	C02385 N
MeSH	Arginine
ChEBI	CHEBI:29016 Y
ChEMBL	CHEMBL212301 N, CHEMBL1485 N
IUPHAR ligand	721
RTECS number	CF1934200 S
ATC code	B05XB01 S
Beilstein Reference	1725411, 1725412 R, 1725413 S
Gmelin Reference	364938 R
3DMet	B01331
Jmol-3D images	Image 1 Image 2
SMILES NC(CCC[nH]:c(:[nH]):[nH2])c(:[o]):[oH] NC(CCCNC(N)=N)C(O)=O
InChI InChI=1S/C6H14N4O2/c7-4(5(11)12)2-1-3-10-6(8)9/h4H,1-3,7H2,(H,11,12)(H4,8,9,10) Y Key: ODKSFYDXXFIFQN-UHFFFAOYSA-N Y
Properties
Molecular formula	C6H14N4O2
Molar mass	174.20 g mol−1
Appearance	White crystals
Odor	Odourless
Melting point	260 °C; 500 °F; 533 K
Boiling point	368 °C (694 °F; 641 K)
Solubility in water	14.87 g/100 mL (20 °C)
Solubility	slightly soluble in ethanol insoluble in ethyl ether
log P	−1.652
Acidity (pKa)	2.488
Basicity (pKb)	11.509
Thermochemistry
Specific heat capacity C	232.8 J K−1 mol−1 (at 23.7 °C)
Std molar entropy So298	250.6 J K−1 mol−1
Std enthalpy of formation ΔfHo298	−624.9–−622.3 kJ mol−1
Std enthalpy of combustion ΔcHo298	−3.7396–−3.7370 MJ mol−1
Hazards
MSDS	External MSDS
GHS pictograms
GHS signal word	WARNING
GHS hazard statements	H319
GHS precautionary statements	P305+351+338
EU classification	Xi
R-phrases	R36
S-phrases	S26
LD50	5110 mg/kg (rat, oral)
Related compounds
Related alkanoic acids	N-Methyl-D-aspartic acid beta-Methylamino-L-alanine Guanidinopropionic acid Theanine Pantothenic acid
Related compounds	Panthenol
Supplementary data page
Structure and properties	n, εr, etc.
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
N (verify) (what is: Y/N?)
Infobox references

Arginine (/ˈɑrdʒɨniːn/, abbreviated as Arg or R) is an α-amino acid. It was first isolated in 1886. The L-form is one of the 20 most common natural amino acids. At the level of molecular genetics, in the structure of the messenger ribonucleic acid mRNA, CGU, CGC, CGA, CGG, AGA, and AGG, are the triplets of nucleotide bases or codons that code for arginine during protein synthesis. In mammals, 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. There are some conditions that put an increased demand on the body for the synthesis of L-arginine, including surgical or other trauma, sepsis and burns. Arginine was first isolated from a lupin seedling extract in 1886 by the Swiss chemist Ernst Schultze.

In general, most healthy people do not need to supplement with arginine because the body usually produces sufficient amounts.

Structure

The amino acid side-chain of arginine consists of a 3-carbon aliphatic straight chain, the distal end of which is capped by a complex guanidinium group.

Delocalization of charge in guanidinium group of L-Arginine

With a pK_a of 12.48, the guanidinium group is positively charged in neutral, acidic, and even most basic environments, and thus imparts basic chemical properties to arginine. Because of the conjugation between the double bond and the nitrogen lone pairs, the positive charge is delocalized, enabling the formation of multiple H-bonds.

Sources

Dietary sources

Arginine is a conditionally nonessential amino acid, meaning that most of the time it can be manufactured by the human body, and does not need to be obtained directly through the diet. The biosynthetic pathway, however, does not produce sufficient arginine, and some must still be consumed through diet. 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, including:

• Animal sources

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, tuna)

• Plant sources

wheat germ and flour, lupins, buckwheat, granola, oatmeal, peanuts, nuts (coconut, pecans, cashews, walnuts, almonds, Brazil nuts, hazelnuts, pinenuts), seeds (pumpkin, sesame, sunflower), chickpeas, cooked soybeans, Phalaris canariensis (canaryseed or alpiste)

Biosynthesis

Arginine is synthesized from citrulline 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 stage.

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 requirement.

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.

Function

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 benefits and functions attributed to oral supplementation of L-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.

Proteins

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.

Precursor

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 endothelium.

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.

Possible increased risk of death after supplementation following heart attack

A clinical trial found that patients taking an L-arginine supplement following a heart attack found no change in the heart's vascular tone or decrease in the symptoms of congestive heart failure (the heart's ability to pump). In fact, six more patients that were taking L-arginine died than those taking a placebo, resulting in early termination of the study with the recommendation that the supplement not be used by heart attack patients. These findings suggest L-arginine is not beneficial post-heart-attack. It has since been found that this research was significantly flawed as the patients did not have raised blood Arginine levels because the source of Arginine used was a cheap internet provider and the Arginine content of the capsules were much lower than the stated 500mg. Therefore the resultant deaths were not likely to be due to Arginine but other factors

Potential medical uses

Lung inflammation and asthma

Inhalation of L-arginine can increase lung inflammation and worsen asthma.

Growth hormone

Intravenously-administered arginine stimulates the secretion of growth hormone, and is used in growth hormone stimulation tests. Two studies have found that oral L-arginine supplementation is also effective at increasing resting GH levels. The first study found that oral preparations of L-arginine are effective at increasing growth hormone levels. In fact, the 9-gram dose resulted in mean peak GH levels of 6.4 (+/- 1.3) microg/L versus placebo levels of 2.9 (+/- 0.7). Another study found similar results. It included resting versus exercise and oral L-arginine versus oral placebo. The authors concluded that "Oral arginine alone (7 g) stimulated GH release, but a greater GH response was seen with exercise alone. The combined effect of arginine before exercise attenuates the GH response... GH production: Ex > Arg+Ex > Arg > placebo" suggesting against supplementing with arginine alone prior to exercise if the goal is to raise GH levels, but concurring with the previous study that oral L-arginine increases GH on days free of significant exercise. In contrast to these two studies that found increased resting GH due to oral arginine supplementation, a third study did not find increase in resting GH levels from oral supplementation. In that study, oral preparations of L-arginine were ineffective at increasing growth hormone levels despite being effective at increasing plasma levels of L-arginine.

MELAS syndrome

Several trials delved into effects of L-arginine in MELAS syndrome, a mitochondrial disease.

Sepsis

Cellular arginine biosynthetic capacity determined by activity of argininosuccinate synthetase (AS) is induced by the same mediators of septic response — endotoxin and cytokines — that induce nitric oxide synthase (NOS), the enzyme responsible for nitric oxide synthesis.

Malate salt

The malate salt of arginine can also be used during the treatment of alcoholic hepatitis and advanced cirrhosis.

Pre-eclampsia

A preliminary study of supplementation with L-arginine and antioxidant vitamins showed that this combination may help to combat abnormally high blood pressure during high-risk pregnancies.

Hypertension

Intravenous infusion of arginine reduces blood pressure in patients with hypertension as well as normal subjects.

A recent meta-analysis showed that L-arginine reduces blood pressure with pooled estimates of 5.4/2.7 mmHg for SBP/DBP.

Erectile dysfunction

Arginine taken in combination with proanthocyanidins or glutamic acid and yohimbine, has also been used as a treatment for erectile dysfunction.

Anxiety

Dietary supplementation of L-arginine taken in combination with L-lysine has been shown potentially useful in treating people subjected to high levels of mental stress and anxiety, in a double-blind, placebo controlled and randomized study, involving 108 Japanese adults. Trait anxiety and state anxiety induced by cognitive stress battery was significantly reduced, and basal levels of the stress hormone cortisol were decreased. The study was funded by Ajinomoto, Co. Inc., an industrial manufacturer of lysine and arginine.

See also

• Arginine glutamate
• AAKG
• Canavanine and canaline are toxic analogs of arginine and ornithine.

References

External links

• NIST Chemistry Webbook
• Mayo Clinic discussion of Arginine.
• National Institute of Health discussion of Arginine.

UpToDate Contents

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• 1. 内皮細胞機能不全 endothelial dysfunction
• 2. 成人における成長ホルモン欠乏症 growth hormone deficiency in adults
• 3. アテローム性動脈硬化症の病因 pathogenesis of atherosclerosis
• 4. 重症患者における栄養補給：経腸栄養 nutrition support in critically ill patients enteral nutrition
• 5. 尿素サイクル障害：管理 urea cycle disorders management

English Journal

• Design and pharmacodynamics of recombinant NZ2114 histidine mutants with improved activity against methicillin-resistant Staphylococcus aureus.

• Chen H1,2,3, Mao R4,5, Teng D2,3, Wang X2,3, Hao Y2,3, Feng X6, Wang J7,8.
• AMB Express.AMB Express.2017 Dec;7(1):46. doi: 10.1186/s13568-017-0345-x. Epub 2017 Feb 22.
• PMID 28229435

• CLK-dependent exon recognition and conjoined gene formation revealed with a novel small molecule inhibitor.

• Funnell T1,2, Tasaki S3, Oloumi A1,2,4, Araki S3, Kong E1,2, Yap D1,2, Nakayama Y3, Hughes CS5, Cheng SG5, Tozaki H3, Iwatani M3, Sasaki S3, Ohashi T3, Miyazaki T3, Morishita N3, Morishita D3, Ogasawara-Shimizu M3, Ohori M3, Nakao S3, Karashima M3, Sano M3, Murai A3, Nomura T3, Uchiyama N3, Kawamoto T3, Hara R3,6, Nakanishi O3,7, Shumansky K1,2, Rosner J1,2,8, Wan A1,2, McKinney S1,2, Morin GB5,9, Nakanishi A3, Shah S1,2, Toyoshiba H10, Aparicio S11,12.
• Nature communications.Nat Commun.2017 Dec;8(1):7. doi: 10.1038/s41467-016-0008-7. Epub 2017 Feb 23.
• PMID 28232751

• Curcumin-loaded nanoliposomes linked to homing peptides for integrin targeting and neuropilin-1-mediated internalization.

• Kangarlou S1, Ramezanpour S2, Balalaie S2, Roudbar Mohammadi S3, Haririan I1,4.
• Pharmaceutical biology.Pharm Biol.2017 Dec;55(1):277-285.
• PMID 27937055

Japanese Journal

• 〔研究ノート〕卵巣摘除された慢性腎臓病モデルラットの骨代謝維持に 対する食餌アルギニンあるいは大豆イソフラボン抽出物 投与の有効性評価に関する基礎的研究

• 学苑 = Gakuen (914), ６-14, 2016-12-01
• NAID 120005903973

• Structure-based molecular design for thermostabilization of N-acetyltransferase Mpr1 involved in a novel pathway of L-arginine synthesis in yeast

• The journal of biochemistry 159(2), 271-277, 2016-02
• NAID 40020763303

• メタノール合成用銅マンガン系触媒へのシリカコートの効果

• Journal of the Society of Inorganic Materials, Japan : セッコウ・石灰・セメント・地球環境の科学 23(380), 11-14, 2016-01
• NAID 40020708151

Related Pictures

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★リンクテーブル★

リンク元	「アルギニン」「L-アルギニン」
拡張検索	「N omega-nitro-L-arginine methyl ester」「L-arginine hydrochloride」「NG-monomethyl-L-arginine」
関連記事	「L」

「アルギニン」

　　[★]

英

arginine, Arg, L-arginine, R

関

アミノ酸、リジン、ヒスチジン、オルニチン回路、オルニチン、アミジノ基。グルタミン酸アルギニン

• 極性、塩基性
• 側鎖：

　-CH2-CH2-CH2-NH-C-(NH2)NH

• グアニジウム基がついている(グアニジンはNH=C(NH2)2)
• ヒゲ三本＋グアニジウム基と覚える。
• 生体内ではグルタミン酸からオルニチン(-CH2-CH2-CH2-NH2, リジンより炭素が1つ少ない)から尿酸サイクルを経て合成される。側鎖の根もとからの炭素源期の数は３つ

「L-アルギニン」

　　[★]

英

L-arginine

化

塩酸L-アルギニン L-arginine hydrochloride

商

アルギU

ESポリタミン、アミカリック、アミグランド、アミノレバンEN、アルギニン、イムネース 、イワコールラブ、セフェピム塩酸塩、セフォチアム、テルフィス、トリゾンラブ、トロンビン、パセトクール、パンスポリン、ヒカリレバン、フィブリノゲンHT、プロテアミン、マキシピーム、ユニカリックＬ

関

アルギニン

「N omega-nitro-L-arginine methyl ester」

　　[★]

Nω-ニトロ-L-アルギニンメチルエステル

関

L-NAME、N(G)-nitro-L-arginine methyl ester、NG-nitro-L-arginine methyl ester、NG-nitroarginine methyl ester

「L-arginine hydrochloride」

　　[★]

塩酸L-アルギニン、塩酸アルギニン

関

arginine hydrochloride

「NG-monomethyl-L-arginine」

　　[★]

NG-モノメチル-L-アルギニン

関

L-NMMA、omega-N-methylarginine

「L」

　　[★]

• リシジン
• リンキング数
• ロイシン
• free ligand concentration