(2S)-2-azaniumyl-5-(carbamoylamino)pentanoate

Base Information

• Chemical Name: (2S)-2-azaniumyl-5-(carbamoylamino)pentanoate
• CAS No.: 372-75-8
• Molecular Formula: C6H13N3O3
• Molecular Weight: 175.188
• Hs Code.: 29241900
• Mol file: 372-75-8.mol

Synonyms:alpha-amino-gamma-ureidovaleric acid;(2S)-2-azaniumyl-5-(carbamoylamino)pentanoate;gamma-ureidonorvaline;L-citrulline zwitterion;CHEBI:57743

Chemical Property of (2S)-2-azaniumyl-5-(carbamoylamino)pentanoate

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 4.7E-07mmHg at 25°C
• Melting Point: 214 °C
• Refractive Index: 26 ° (C=8, 6mol/L HCl)
• Boiling Point: 386.7 °C at 760 mmHg
• PKA: 2.43(at 25℃)
• Flash Point: 187.7 °C
• PSA: 118.44000
• Density: 1.289 g/cm³
• LogP: 0.63830
• Storage Temp.: Store at 0-5°C
• Solubility.: Aqueous Acid (Sparingly). Water (Slightly)
• Water Solubility.: 200 g/L (20 ºC)
• XLogP3: -3.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 175.09569129
• Heavy Atom Count: 12
• Complexity: 166

Purity/Quality:

99.3% ^*data from raw suppliers

L-Citrulline-d7 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(CC(C(=O)[O-])[NH3+])CNC(=O)N
• Isomeric SMILES: C(C[C@@H](C(=O)[O-])[NH3+])CNC(=O)N
• Bioavailability and Properties: L-citrulline is a natural precursor of L-arginine and is more bioavailable than L-arginine due to its ability to avoid hepatic first-pass metabolism and longer circulation time. It possesses antioxidant and vasodilation properties and is an integral part of the human nitric oxide system.
• Enzymatic Regulation: The metabolism of L-citrulline involves key enzymes such as nitric oxide synthase (NOS), ornithine transcarbamylase (OTC), and argininosuccinate synthase (ASS), which are responsible for CIT synthesis and catabolism in mammals, respectively. These enzymes regulate CIT's involvement in various metabolic pathways.
• Synthesis and Sources: Citrulline is synthesized from ornithine and carbamoyl phosphate in the urea cycle and is also produced from arginine as a by-product of the reaction catalyzed by NOS family enzymes. It is found primarily in watermelon, cucumbers, and other melons, with watermelon being the most naturally rich source.
• Supplementation and Effects: L-citrulline is commonly supplemented in the form of citrulline malate, and its benefits may be attributed to the synergistic combination of L-citrulline and malate at the intramuscular metabolic level. Pharmacokinetic studies have shown that plasma citrulline reaches peak concentration between 40 and 60 minutes after ingestion, while plasma arginine peaks between 80 and 120 minutes, with elevated concentrations lasting up to 8 hours.
• Metabolic Pathways: L-citrulline plays a crucial role in the urea cycle in the liver, responsible for ammonia elimination in the form of urea. During high-intensity exercise, citrulline supplementation may aid in ammonia detoxification, decrease lactate production, and enhance aerobic utilization of pyruvate, thereby improving muscle function and reducing fatigue.
• Metabolic Characteristics: L-citrulline is an organic compound and a non-essential amino acid synthesized endogenously by the body. It is not involved in protein synthesis but is an important component of metabolic pathways such as arginine biosynthesis, the Arg-CIT-nitric oxide cycle, and the urea cycle.
• Role in Sustainable Practices: Watermelon and its by-products, such as the rind, can be utilized for citrulline extraction, promoting sustainability in the fresh-cut watermelon industry and supporting a circular economy model.

Technology Process of (2S)-2-azaniumyl-5-(carbamoylamino)pentanoate

There total 19 articles about (2S)-2-azaniumyl-5-(carbamoylamino)pentanoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

L-arginine (74-79-3,25212-18-4) → Citrulline (372-75-8)

Guidance literature:

for 46 - 120h; Product distribution / selectivity; Enzymatic reaction;

Reference yield:

L-citrulline copper complex → Citrulline (372-75-8)

Guidance literature:

With sodium sulfide; In water; Reagent/catalyst; Large scale;

Reference yield:

N-hydroxy-L-arginine → Citrulline (372-75-8)

Guidance literature:

With dihydrogen peroxide; Cl₈TPPFe(III)Cl; In various solvent(s); at 20 ℃;

DOI:10.1016/j.tetlet.2005.02.088

upstream raw materials:

L-ornithine

L-arginine

L-carglumic acid

L-arginine hydrochloride

Downstream raw materials:

N-carbamoyl-L-leucine

D-2-carbamoylamino-3-phenylpropionic acid

L-arginine

N^α-benzyloxy-carbonyl-L-citrulline

Refernces

• 1、 Tejero, Jesus,Biswas, Ashis,Haque, Mohammad Mahfuzul,Wang, Zhi-Qiang,Hemann, Craig,Varnado, Cornelius L.,Novince, Zachary,Hille, Russ,Goodwin, Douglas C.,Stuehr, Dennis J.. "Mesohaem substitution reveals how haem electronic properties can influence the kinetic and catalytic parameters of neuronal NO synthase". . p. 163 - 174. Retrieved 2011.
• 2、 Lu, Xuefeng,Galkin, Andrey,Herzberg, Osnat,Dunaway-Mariano, Debra. "Arginine Deiminase Uses an Active-Site Cysteine in Nucleophilic Catalysis of L-Arginine Hydrolysis". . p. 5374 - 5375. Retrieved 2004.
• 3、 Fang, Jianguo,Ji, Haitao,Lawton, Graham R.,Xue, Fengtian,Roman, Linda J.,Silverman, Richard B.. "L337H mutant of rat neuronal nitric oxide synthase resembles human neuronal nitric oxide synthase toward inhibitors". . p. 4533 - 4537. Retrieved 2009.
• 4、 Marmion,Murphy,Nolan. "Ruthenium(III) readily abstracts NO from L-arginine, the physiological precursor to NO, in the presence of H2O2. A remarkably simple model system for NO synthases.". . p. 1870 - 1871. Retrieved 2001.
• 5、 Kuropteva,Baider,Nagler,Bogatyrenko,Belaia. "l-Arginine and nitric oxide synthesis in the cells with inducible NO synthase". . p. 174 - 180. Retrieved 2019/04/25.
• 6、 -. "Method for preparing L-citrulline crude product and L-citrulline prepared through method". Paragraph 0033-0108. . Retrieved 2017/05/05.