| Identification | Back Directory | [Name]
Arginine | [CAS]
7004-12-8 | [Synonyms]
ARGININE
FMOC-L-ARG(PBF)-OPFP
FMOC-ARGININE(PBF)-OPFP
5-Guanidino-2-aminopentanoic acid
FMOC-N-OMEGA-(2,2,4,6,7-PENTAMETHYLDIHYDROBENZOFURAN-5-SULFONYL)-L-ARGININE PENTAFLUOROPHENYL ESTER
N-ALPHA-FMOC-N'-2,2,4,6,7-PENTAMETHYLDIHYDROBENZOFURAN-5-SULFONYL-L-ARGININE PENTAFLUORPHENYL ESTER
N-ALPHA-FMOC-NG-(2,2,4,6,7-PENTAMETHYLDIHYDROBENZOFURAN-5-SULFONYL)-L-ARGININE PENTAFLUOROPHENYL ESTER | [Molecular Formula]
C40H39F5N4O7S | [MDL Number]
MFCD00237040 | [MOL File]
7004-12-8.mol | [Molecular Weight]
814.82 |
| Chemical Properties | Back Directory | [storage temp. ]
-15°C | [pka]
1.82(at 25℃) | [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) | [InChIKey]
ODKSFYDXXFIFQN-UHFFFAOYSA-N | [SMILES]
C(C(N)C(=O)O)CCNC(=N)N | [Uses]
Arginine is a nonessential amino acid that exists as white crystals or
powder. it is soluble in water. it is used to improve the biological
quality of the total protein in a food which contains naturally occur-
ring primarily intact proteins and as a nutrient and dietary
supplement. |
| Hazard Information | Back Directory | [Chemical Properties]
Prisms from water containing two molecules of H2O, anhydrous plates from alcohol solution. Dehydrates at 105C, decomposes at 244C. Sparingly soluble in alcohol; insoluble in ether. | [Definition]
An essential amino acid for rats, occurring naturally in the l(+) form. Available as glutamate and hydrochloride. | [Description]
Arginine (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 people do not need to take arginine supplements because the body usually produces enough. | [Physical properties]
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.
With a pKa 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. | [Occurrence]
Dietary sources
Arginine is a conditionally nonessential amino acid, meaning 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 who have 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, 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 tri phosphate (ATP) to adenosine mono phosphate (AMP), i.e., two ATP equivalents.
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. | [Biological Functions]
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)
Reduces healing time of injuries (particularly bone)
Quickens repair time of damaged tissue
Helps decrease blood pressure in clinical hypertensive subjects. | [Synthesis Reference(s)]
Tetrahedron, 44, p. 805, 1988 DOI: 10.1016/0040-4039(96)01716-9
Tetrahedron Letters, 37, p. 7557, 1996 DOI: 10.1016/0040-4039(96)01716-9
Chemical and Pharmaceutical Bulletin, 29, p. 2825, 1981 DOI: 10.1248/cpb.29.2825 |
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