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DL-Arginine

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Arginine is an alpha-amino acid that is glycine in which the alpha-is substituted by a 3-guanidinopropyl group. It has a role as a fundamental metabolite. It is an alpha-amino acid, a member of guanidines and a polar amino acid. It contains a 3-carbamimidamidopropyl group. It is a conjugate base of an argininium(1+). It is a conjugate acid of an argininate.

Category

DL-Amino Acids

Catalog number

BAT-007649

CAS number

7200-25-1

Molecular Formula

C6H14N4O2

Molecular Weight

174.20

IUPAC Name

2-amino-5-(diaminomethylideneamino)pentanoic acid

Synonyms

H-DL-Arg-OH; (±)-Arginine; 2-Amino-5-(carbamimidamido)pentanoic Acid; 2-Amino-5-guanidinopentanoic Acid; D(-)-Arginine; arginin; (2S)-2-amino-5-(diaminomethylideneamino)pentanoic acid; H DL Arg OH

Related CAS

74-79-3 (L-isomer)

Appearance

White to off-white powder

Purity

97.0%-102.0% (Assay)

Density

1.460 g/cm3

Melting Point

228-232 °C

Boiling Point

409.1 °C at 760 mmHg

Storage

Store at RT

Solubility

water, 1e+006 mg/L @ 25 °C (est)

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)

InChI Key

ODKSFYDXXFIFQN-UHFFFAOYSA-N

Canonical SMILES

C(CC(C(=O)O)N)CN=C(N)N

DL-Arginine, a derivative of the amino acid arginine, finds diverse applications across various fields. Here are the key applications presented with a high degree of perplexity and burstiness:

Nutritional Supplements: Integral to dietary supplementation, DL-Arginine plays a crucial role in protein synthesis and nitric oxide generation. Athletes and bodybuilders leverage DL-Arginine to enhance performance, accelerate recovery, and stimulate muscle hypertrophy. Furthermore, it bolsters cardiovascular well-being by enhancing blood circulation and mitigating blood pressure, showcasing its multifaceted benefits.

Pharmaceutical Industry: Within the pharmaceutical domain, DL-Arginine serves as a valuable component in formulating medications targeted at cardiovascular ailments. Through its vasodilatory properties, it aids in the management of conditions like hypertension and angina. Moreover, ongoing research explores its potential in augmenting wound healing processes and fortifying immune responses, highlighting its therapeutic potential.

Cosmetic Industry: Embraced by the cosmetic sector, DL-Arginine features prominently in skincare formulations due to its hydrating and anti-aging attributes. It fosters collagen synthesis, thereby preserving skin suppleness and diminishing wrinkles. Additionally, DL-Arginine facilitates skin barrier restoration and shields against environmental aggressors, making it an indispensable ally in skincare regimes.

Biotechnology Research: In the realm of biotechnology, DL-Arginine assumes a pivotal role in cell culture media, nurturing the growth of diverse cell lineages. Its involvement in metabolic pathways renders it indispensable for scrutinizing cellular metabolism and protein biosynthesis. Researchers harness DL-Arginine to fine-tune cell cultivation conditions, optimizing the production yield of recombinant proteins, elucidating its significance in advancing biotechnological endeavors.

1.Ontogenetic Variation in Biological Activities of Venoms from Hybrids between Bothrops erythromelas and Bothrops neuwiedi Snakes.

Santoro ML1, do Carmo T1, Cunha BH1, Alves AF1, Zelanis A2, Serrano SM2, Grego KF3, Sant'Anna SS3, Barbaro KC4, Fernandes W3. PLoS One. 2015 Dec 29;10(12):e0145516. doi: 10.1371/journal.pone.0145516. eCollection 2015.

Lance-headed snakes are found in Central and South America, and they account for most snakebites in Brazil. The phylogeny of South American pitvipers has been reviewed, and the presence of natural and non-natural hybrids between different species of Bothrops snakes demonstrates that reproductive isolation of several species is still incomplete. The present study aimed to analyze the biological features, particularly the thrombin-like activity, of venoms from hybrids born in captivity, from the mating of a female Bothrops erythromelas and a male Bothrops neuwiedi, two species whose venoms are known to display ontogenetic variation. Proteolytic activity on azocoll and amidolytic activity on N-benzoyl-DL-arginine-p-nitroanilide hydrochloride (BAPNA) were lowest when hybrids were 3 months old, and increased over body growth, reaching values similar to those of the father when hybrids were 12 months old. The clotting activity on plasma diminished as hybrids grew; venoms from 3- and 6-months old hybrids showed low clotting activity on fibrinogen (i.

2.Effect of chlorhexidine chip in the treatment of chronic periodontitis.

Kumar AJ1, Ramesh Reddy BV1, Chava VK1. J Nat Sci Biol Med. 2014 Jul;5(2):268-72. doi: 10.4103/0976-9668.136159.

AIMS: The evaluation of clinical and specific microbiological changes associated with chlorhexidine chip in the chronic periodontitis patients.

3.Effect of midgut proteolytic activity on susceptibility of lepidopteran larvae to Bacillus thuringiensis subsp. Kurstaki.

Talaei-Hassanloui R1, Bakhshaei R1, Hosseininaveh V1, Khorramnezhad A1. Front Physiol. 2014 Jan 16;4:406. doi: 10.3389/fphys.2013.00406. eCollection 2013.

Bacillus thuringiensis (Bt) is the most effective microbial control agent for controlling numerous species from different insect orders. All subspecies and strains of B. thuringiensis can produce a spore and a crystalline parasporal body. This crystal which contains proteinaceous protoxins is dissolved in the alkaline midgut, the resulting molecule is then cleaved and activated by proteolytic enzymes and acts as a toxin. An interesting aspect of this activation process is that variations in midgut pH and protease activity have been shown to account for the spectrum of some Bt proteins activity. Thus, an important factor that could be a determinant of toxin activity is the presence of proteases in the midgut microenvironment of susceptible insects. Reciprocally, any alteration in the midgut protease composition of the host can result in resistance to Bt. Here in this paper, we reviewed this processes in general and presented our assays to reveal whether resistance mechanism to Bt in Diamondback Moth (DbM) larvae could be due to the function of the midgut proteases? We estimated LC50 for both probable susceptible and resistant populations in laboratory and greenhouse tests.

4.Kinetics of trypsin-catalyzed hydrolysis determined by isothermal titration calorimetry.

Maximova K1, Trylska J2. Anal Biochem. 2015 Oct 1;486:24-34. doi: 10.1016/j.ab.2015.06.027. Epub 2015 Jun 25.

Isothermal titration calorimetry (ITC) was applied to determine enzymatic activity and inhibition. We measured the Michaelis-Menten kinetics for trypsin-catalyzed hydrolysis of two substrates, casein (an insoluble macromolecule substrate) and Nα-benzoyl-dl-arginine β-naphthylamide (a small substrate), and estimated the thermodynamic parameters in the temperature range from 20 to 37°C. The inhibitory activities of reversible (small molecule benzamidine) and irreversible (small molecule phenylmethanesulfonyl fluoride and macromolecule α1-antitrypsin) inhibitors of trypsin were also determined. We showed the usefulness of ITC for fast and direct measurement of inhibition constants and half-maximal inhibitory concentrations and for predictions of the mechanism of inhibition. ITC kinetic assays could be an easy and straightforward way to estimate Michaelis-Menten constants and the effectiveness of inhibitors as well as to predict the inhibition mechanism.