Adenylosuccinic Acid ammonium salt | CAS#unknown | Purine nucleotide intermediate

MedKoo Cat#: 464806 | Name: Adenylosuccinic Acid ammonium salt

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Adenylosuccinic acid is a purine nucleotide and an intermediate in the purine nucleotide cycle. It is converted into AMP and fumarate by adenylosuccinate lyase in the cytosol. Adenylosuccinic acid (10 µM) inhibits calcium-induced activation of non-selective cation channels in isolated rat brown adipocytes in a patch-clamp assay. Adenylosuccinic acid (10 µM) increases glucose-induced insulin exocytosis in 832/13 INS-1 pancreatic β-cells. It induces contractions in isolated guinea pig uterus strips when used at a concentration of 100 µM.

Chemical Structure

Adenylosuccinic Acid ammonium salt

CAS#unknown

Theoretical Analysis

MedKoo Cat#: 464806

Name: Adenylosuccinic Acid ammonium salt

CAS#: unknown

Chemical Formula: C14H30N9O11P

Exact Mass: 0.0000

Molecular Weight: 531.42

Elemental Analysis: C, 31.64; H, 5.69; N, 23.72; O, 33.12; P, 5.83

Price and Availability

Size	Price	Availability	Quantity
50mg	USD 850.00	2 Weeks

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Related CAS #

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Synonym

Adenylosuccinic Acid ammonium salt; Adenylosuccinic-Acid ammonium salt;

IUPAC/Chemical Name

ammonium (9-((2R,3R,4S,5R)-3,4-dihydroxy-5-((phosphonatooxy)methyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)-L-aspartate

InChi Key

XCLZBEXZAOLWGA-BFHDGDRYSA-N

InChi Code

InChI=1S/C14H18N5O11P.4H3N/c20-7(21)1-5(14(24)25)18-11-8-12(16-3-15-11)19(4-17-8)13-10(23)9(22)6(30-13)2-29-31(26,27)28;;;;/h3-6,9-10,13,22-23H,1-2H2,(H,20,21)(H,24,25)(H,15,16,18)(H2,26,27,28);4*1H3/t5-,6+,9+,10+,13+;;;;/m0..../s1

SMILES Code

[O-]P(OC[C@@H](O[C@]1(N2C=NC3=C(N=CN=C32)N[C@H](C([O-])=O)CC([O-])=O)[H])[C@H]([C@H]1O)O)([O-])=O.[NH4+].[NH4+].[NH4+].[NH4+]

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

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.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

	Solvent	mg/mL	mM	comments
Solubility
	PBS (pH 7.2)	10.0	0.00

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 531.42 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Timpani CA, Goodman CA, Stathis CG, White JD, Mamchaoui K, Butler-Browne G, Gueven N, Hayes A, Rybalka E. Adenylosuccinic acid therapy ameliorates murine Duchenne Muscular Dystrophy. Sci Rep. 2020 Jan 24;10(1):1125. doi: 10.1038/s41598-020-57610-w. PMID: 31980663; PMCID: PMC6981178. 2: Rybalka E, Goodman CA, Campelj DG, Hayes A, Timpani CA. Adenylosuccinic acid: a novel inducer of the cytoprotectant Nrf2 with efficacy in Duchenne muscular dystrophy. Curr Med Res Opin. 2021 Mar;37(3):465-467. doi: 10.1080/03007995.2020.1865699. Epub 2021 Jan 29. PMID: 33331789. 3: Dewulf JP, Marie S, Nassogne MC. Disorders of purine biosynthesis metabolism. Mol Genet Metab. 2022 Jul;136(3):190-198. doi: 10.1016/j.ymgme.2021.12.016. Epub 2021 Dec 30. PMID: 34998670. 4: Liu X, Kimmey JM, Matarazzo L, de Bakker V, Van Maele L, Sirard JC, Nizet V, Veening JW. Exploration of Bacterial Bottlenecks and Streptococcus pneumoniae Pathogenesis by CRISPRi-Seq. Cell Host Microbe. 2021 Jan 13;29(1):107-120.e6. doi: 10.1016/j.chom.2020.10.001. Epub 2020 Oct 28. PMID: 33120116; PMCID: PMC7855995. 5: Dutto I, Gerhards J, Herrera A, Souckova O, Škopová V, Smak JA, Junza A, Yanes O, Boeckx C, Burkhalter MD, Zikánová M, Pons S, Philipp M, Lüders J, Stracker TH. Pathway-specific effects of ADSL deficiency on neurodevelopment. Elife. 2022 Feb 8;11:e70518. doi: 10.7554/eLife.70518. PMID: 35133277; PMCID: PMC8871376. 6: BALLIO A, SERLUPI-CRESCENZI G. Isolation of adenylosuccinic acid from Penicillium chrysogenum. Nature. 1957 Jan 19;179(4551):154. doi: 10.1038/179154a0. PMID: 13400124. 7: CARTER CE, COHEN LH. The preparation and properties of adenylosuccinase and adenylosuccinic acid. J Biol Chem. 1956 Sep;222(1):17-30. PMID: 13366975. 8: DAVEY CL. Synthesis of adenylosuccinic acid in preparations of mammalian skeletal muscle. Nature. 1959 Apr 4;183(4666):995-6. doi: 10.1038/183995a0. PMID: 13644270. 9: Jurecka A, Zikanova M, Kmoch S, Tylki-Szymańska A. Adenylosuccinate lyase deficiency. J Inherit Metab Dis. 2015 Mar;38(2):231-42. doi: 10.1007/s10545-014-9755-y. Epub 2014 Aug 12. PMID: 25112391; PMCID: PMC4341013. 10: Park KW, Tyagi AK, Cooney DA. A radiometric technique for the measurement of adenylosuccinate lyase. J Biochem Biophys Methods. 1980 May;2(5):291-7. doi: 10.1016/0165-022x(80)90053-6. PMID: 7052946. 11: FROMM HJ. On the equilibrium and mechanism of adenylosuccinic acid synthesis. Biochim Biophys Acta. 1958 Aug;29(2):255-62. doi: 10.1016/0006-3002(58)90182-3. PMID: 13572341. 12: Bonsett CA, Rudman A. The dystrophin connection--ATP? Med Hypotheses. 1992 Jun;38(2):139-54. doi: 10.1016/0306-9877(92)90087-s. PMID: 1326712. 13: Spiegel EK, Colman RF, Patterson D. Adenylosuccinate lyase deficiency. Mol Genet Metab. 2006 Sep-Oct;89(1-2):19-31. doi: 10.1016/j.ymgme.2006.04.018. Epub 2006 Jul 12. PMID: 16839792. 14: Van den Berghe G, Jaeken J. Adenylosuccinase deficiency. Adv Exp Med Biol. 1986;195 Pt A:27-33. doi: 10.1007/978-1-4684-5104-7_4. PMID: 3014834. 15: Jayaram HN, Cooney DA. Analogs of L-aspartic acid in chemotherapy for cancer. Cancer Treat Rep. 1979 Jun;63(6):1095-108. PMID: 38003. 16: Chheda GB. Isolation and characterization of N6-succinyladenosine from human urine. Nucleic Acids Res. 1977 Mar;4(3):739-46. doi: 10.1093/nar/4.3.739. PMID: 17101; PMCID: PMC342476. 17: Chen X, Wu J, Song W, Zhang L, Wang H, Liu L. Fumaric acid production by Torulopsis glabrata: engineering the urea cycle and the purine nucleotide cycle. Biotechnol Bioeng. 2015 Jan;112(1):156-67. doi: 10.1002/bit.25334. Epub 2014 Oct 10. PMID: 25060134. 18: Brosh S, Zoref-Shani E, Danziger E, Bromberg Y, Sperling O, Sidi Y. Adenine nucleotide metabolism in primary rat neuronal cultures. Int J Biochem Cell Biol. 1996 Mar;28(3):319-28. doi: 10.1016/1357-2725(95)00134-4. PMID: 8920641. 19: HAMPTON A. Studies of the action of adenylosuccinase with 6-thio analogues of adenylosuccinic acid. J Biol Chem. 1962 Feb;237:529-35. PMID: 13904242. 20: Patterson D. Biochemical genetics of Chinese hamster cell mutants with deviant purine metabolism. IV. Isolation of a mutant which accumulates adenylosuccinic acid and succinylaminoimidazole carboxamide ribotide. Somatic Cell Genet. 1976 May;2(3):189-203. doi: 10.1007/BF01538958. PMID: 1028168.