Guanidinosuccinic acid

• CAS: 6133-30-8
• Catalog Number: ACM6133308
• Category: Main Products
• Molecular Weight: 175.14 g/mol
• Molecular Formula: C5H9N3O4
• Synonyms: Guanidinosuccinic acid; NSC 49078; NSC-49078; NSC49078; L-N-Amidinoaspartic acid
• IUPAC Name: carbamimidoyl-L-aspartic acid
• SMILES: O=C(O)C[C@@H](C(O)=O)NC(N)=N
• InChI: InChI=1S/C5H9N3O4/c6-5(7)8-2(4(11)12)1-3(9)10/h2H,1H2,(H,9,10)(H,11,12)(H4,6,7,8)/t2-/m0/s1
• InChI Key: VVHOUVWJCQOYGG-REOHCLBHSA-N
• Boiling Point: 366.9ºC at 760 mmHg
• Flash Point: 175.7ºC
• Density: 1.74g/cm³
• Appearance: Solid powder
• Shelf Life: >2 years if stored properly
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• Drug Formulation: This drug may be formulated in DMSO
• Elemental Analysis: C, 34.29; H, 5.18; N, 23.99; O, 36.54
• Exact Mass: 175.0593
• HS Tariff Code: 2934.99.9001
• Shipping: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
• Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Case Study

Guanidinosuccinic Acid as an Intercalation Modifier for Self-Healing Anticorrosion Coatings

Li, Ji, et al. Applied Surface Science 480 (2019): 384-394.

2-Guanidinosuccinic acid (GSA) is synthesized from L-aspartic acid and intercalated into lithium-aluminum layered double hydroxide films as an environmentally friendly corrosion inhibitor that confers self-repairing and self-antibacterial functions on aluminum alloy surfaces.
Experimental Protocol: GSA is prepared by reacting L-aspartic acid (13.1 g) with O-methylisourea sulfate in 2 mol/L sodium hydroxide at pH 10.1 for about 40 h, followed by acidification to pH 3.4. A6N01-T5 aluminum alloy is immersed in a conversion solution containing lithium nitrate, lithium hydroxide and 0.9-3.6 g/L GSA at 60°C for 20 min to grow films about 100 nm thick; corrosion performance is assessed in 3.5 wt% sodium chloride solution by polarization curves, electrochemical impedance and neutral salt spray for 300 h, and antibacterial efficiency is measured against Escherichia coli and Bacillus subtilis.
Performance Evaluation: The corrosion current density falls from 2.092 to 0.010 microampere cm^-2 for the GSA-modified film, and artificial scratches 25 micrometers wide self-repair within 18 days of immersion. Antibacterial efficiency reaches 96.42% against E. coli and 95.1% against B. subtilis, remaining at 97.55% after the self-repairing process, demonstrating sustained multifunctional corrosion protection.

Guanidinosuccinic Acid as a Uremic Toxin for Blood-Cerebrospinal Fluid Pharmacokinetics

Kasai, Yasuyuki, et al. Drug Metabolism and Pharmacokinetics 29.1 (2014): 97-100.

Guanidinosuccinic acid (GSA), a guanidino uremic toxin, serves as the study analyte for quantifying how renal failure alters its elimination from circulating blood and how the blood-cerebrospinal fluid barrier controls its distribution to the central nervous system.
Experimental Protocol: GSA (1 micromol/kg) is administered intravenously to normal rats and to rats with cisplatin-induced renal failure induced by 5 mg/kg intraperitoneal injection 3 days earlier, and plasma concentrations are measured by liquid chromatography-tandem mass spectrometry. Blood-to-cerebrospinal fluid influx clearance is derived by integration plot analysis after a 12.5 micromol/kg dose, while efflux is characterized after intracerebroventricular administration of 0.05 micromol/kg in normal rats.
Performance Evaluation: In cisplatin-treated rats the area under the curve and half-life of GSA are 7.3-fold greater than in normal rats, and total body clearance falls by 88%, from 867 to 107 microliters per minute per rat, whereas the distribution volume at steady state is unchanged. Cerebrospinal fluid elimination clearance (15.5 microliters per minute per rat) exceeds the blood-to-cerebrospinal fluid influx clearance (0.176) by 88-fold, explaining the low cerebrospinal fluid-to-plasma ratio of GSA and the transporter-mediated maintenance of low central nervous system levels.

Guanidinosuccinic Acid as a Neurotoxic Metabolite in Argininosuccinate Lyase Deficiency

Diez-Fernandez, Carmen, et al. Journal of inherited metabolic disease 42.6 (2019): 1077-1087.

Guanidinosuccinic acid (GSA) is investigated as a putatively neurotoxic metabolite accumulating in argininosuccinate lyase deficiency, and its effects on developing brain cells are examined to clarify the pathophysiology of neurological complications in this urea cycle disorder.
Experimental Protocol: Rat 3D organotypic brain cell aggregates are exposed to GSA at 1, 10, 30 or 100 micromolar, alone or combined with argininosuccinic acid (100 micromolar), ammonium chloride (5 mM) or creatine (1 mM), during days in vitro 5-13 (immature) and 14-22 (mature); cultures are harvested on day 13 and 22 for western blotting, immunohistochemistry and metabolite analysis.
Performance Evaluation: Exposure to 100 micromolar GSA is highly toxic in mature cultures, causing massive lactate dehydrogenase release, undetectable glucose, and near-complete loss of the astrocytic marker glial fibrillary acidic protein; 30 micromolar GSA also aggravates argininosuccinic acid-induced astrocyte damage. Oligodendrocytes remain largely unaffected, consistent with their lack of argininosuccinate lyase expression. Creatine supplementation reverts the toxicity of both GSA and argininosuccinic acid toward astrocytes and neurons. GSA does not alter intracellular arginine, creatine or guanidinoacetate levels, whereas argininosuccinic acid exerts an anti-apoptotic effect, revealing distinct mechanisms by which guanidino metabolites may contribute to neurotoxicity.

Custom Q&A

What is the molecular formula of Guanidinosuccinic acid?

The molecular formula of Guanidinosuccinic acid is C5H9N3O4.

What are the synonyms for Guanidinosuccinic acid?

The synonyms for Guanidinosuccinic acid are N-Amidino-L-aspartic acid and Guanidinosuccinate.

What is the molecular weight of Guanidinosuccinic acid?

The molecular weight of Guanidinosuccinic acid is 175.14 g/mol.

What is the IUPAC name of Guanidinosuccinic acid?

The IUPAC name of Guanidinosuccinic acid is (2S)-2-(diaminomethylideneamino)butanedioic acid.

In which organisms is Guanidinosuccinic acid found?

Guanidinosuccinic acid is found in Diospyros virginiana, Malus pumila, and other organisms.

What type of compound is Guanidinosuccinic acid in terms of uremic toxins?

Guanidinosuccinic acid is a uremic toxin.

How does Guanidinosuccinic acid arise metabolically?

Guanidinosuccinic acid arises from the oxidation of argininosuccinic acid (ASA) by free radicals.

What is the effect of uremic toxins like Guanidinosuccinic acid on the body?

Chronic exposure to uremic toxins like Guanidinosuccinic acid can lead to conditions such as renal damage, chronic kidney disease, and cardiovascular disease.

How can the build-up of Guanidinosuccinic acid be reduced in end-stage renal disease?

The build-up of Guanidinosuccinic acid in end-stage renal disease can be reduced by replacing specific amino acid mixtures and monitoring serum levels of related toxins.

What is another name for Guanidinosuccinic acid in the Toxin and Toxin Target Database?

In the Toxin and Toxin Target Database, Guanidinosuccinic acid is also referred to as (2S)-2-(diaminomethylideneamino)butanedioic acid.

Synthetic Use

Upstream Synthesis Route 1

• 56-84-8
• 2986-19-8

• 6133-30-8

Reference: [1]Ratner et al.
[Journal of Biological Chemistry, 1953, vol. 204, p. 95,108]

Upstream Synthesis Route 2

• 56-84-8
• 2440-60-0

• 6133-30-8

Reference: [1]Walker
[Archives of Biochemistry, 1955, vol. 59, p. 233,234, 240]

Upstream Synthesis Route 3

• 56-84-8
• 867-44-7

• 6133-30-8

Reference: [1]Pant,E.
[Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1964, vol. 335, p. 272 - 274]