4542-23-8

Basic information

• Product Name: (2S)-2-[[9-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]amino]butanedioic acid
• Synonyms: (2S)-2-[[9-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]amino]butanedioic acid;Succinyladenosine;N6-Succinyl Adenosine;(S)-N-(1,2-Dicarboxyethyl)adenosine;6-(1,2-DicarboxyethylaMino) -9-β-D-ribofuranosylpurine;N-(9-β-D-Ribofuranosyl-9H-purin-6-yl)-L-aspartic Acid;Succinoadenosine
• CAS NO: 4542-23-8
• Molecular Formula: C₁₄H₁₇N₅O₈
• Molecular Weight: 383.3135
• Product Categories: Bases & Related Reagents;Chiral Reagents;Intermediates & Fine Chemicals;Nucleotides;Pharmaceuticals
• Mol File: 4542-23-8.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 816.4°Cat760mmHg
• Flash Point: 447.6°C
• Appearance: /
• Density: 2.02g/cm³
• Vapor Pressure: 3.44E-28mmHg at 25°C
• Refractive Index: 1.826
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated)
• CAS DataBase Reference: (2S)-2-[[9-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]amino]butanedioic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-2-[[9-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]amino]butanedioic acid(4542-23-8)
• EPA Substance Registry System: (2S)-2-[[9-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]amino]butanedioic acid(4542-23-8)

Safety Data

• Hazardous Substances Data: 4542-23-8(Hazardous Substances Data)

Usage

Description

(2S)-2-[[9-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]amino]butanedioic acid, also known as Succinyladenosine (S-Ado), is an aspartic acid derivative that plays a significant role as a biochemical marker for adenylosuccinase deficiency. This genetic defect is associated with the impairment of purine de novo synthesis. S-Ado is typically undetectable in the cerebrospinal fluid (CSF) of children without this defect, making it a valuable diagnostic tool.

Uses

1. Used in Diagnostic Applications:
(2S)-2-[[9-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]amino]butanedioic acid is used as a biochemical marker for the detection of adenylosuccinase deficiency in the cerebrospinal fluid (CSF) of children. The presence of S-Ado in the CSF indicates the genetic defect in purine de novo synthesis, aiding in the diagnosis and treatment of the condition.
2. Used in Research and Development:
In the field of medical and biochemical research, (2S)-2-[[9-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]amino]butanedioic acid serves as a crucial compound for understanding the mechanisms and pathways involved in adenylosuccinase deficiency. This knowledge can be applied to develop new therapeutic strategies and improve existing treatments for the genetic disorder.
3. Used in Pharmaceutical Industry:
(2S)-2-[[9-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]amino]butanedioic acid may be utilized in the development of new drugs targeting adenylosuccinase deficiency. By understanding the molecular structure and function of S-Ado, researchers can design and synthesize novel compounds that can potentially correct or alleviate the effects of the genetic defect.
4. Used in Clinical Trials and Studies:
In clinical research, (2S)-2-[[9-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]amino]butanedioic acid can be employed as a biomarker to monitor the progress and effectiveness of treatments for adenylosuccinase deficiency. This can help researchers and clinicians evaluate the safety and efficacy of new therapeutic approaches and make informed decisions regarding patient care.

InChI:InChI=1/C14H17N5O8/c20-2-6-9(23)10(24)13(27-6)19-4-17-8-11(15-3-16-12(8)19)18-5(14(25)26)1-7(21)22/h3-6,9-10,13,20,23-24H,1-2H2,(H,21,22)(H,25,26)(H,15,16,18)/t5-,6+,9+,10+,13+/m0/s1

Upstream product

• 342-69-8 6-methylmercaptopurine riboside 
• 617-45-8 aspartic Acid 
• 19046-78-7 N-(purine-6-yl)-L-aspartic acid 9-β-D-ribofuranoside-5'-phosphate 
• 5987-73-5 2',3',5'-O-triacetyl-6-chloroinosine 
• 132089-81-7 6-(4-chlorophenylthio)-9-β-D-ribofuranosyl-9H-purine 
• 132089-82-8 6-(4-chlorophenylthio)-9-(2,3-O-cyclopentylidene-β-D-ribofuranosyl)-9H-purine 
• 132089-84-0 6-(4-chlorophenylsulphinyl)-9-(2,3-O-cyclopentylidene-β-D-ribofuranosyl)-9H-purine 
• 132089-83-9 6-(4-chlorophenylsulphonyl)-9-(2,3-O-cyclopentylidene-β-D-ribofuranosyl)-9H-purine 
• 132089-80-6 6-(4-chlorophenylsulfanyl)-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-9H-purine 
• 132089-85-1 dibenzyl-N-<9-(2,3-O-cyclopentylidene-β-D-ribofuranosyl)-9H-purin-6-yl>-L-aspartate 
• 58-63-9 Inosine 
• 3181-38-2 2',3',5'-tri-O-acetylinosine 

Downstream Products

• 75-07-0 acetaldehyde 
• 58-61-7 adenosine 

Relevant articles and documents

An Unambiguous Synthesis of Adenylosuccinic Acid and its Constituent Nucleoside

6-(4-Chlorophenylthio)-9-(2,3-O-cyclopentylidene-β-D-ribofuranosyl)-9H-purine (7) is prepared from 6-chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-9H-purine (5) in three steps and is then converted, by treatment with 3-chloroperbenzoic acid, into the corresponding sulphoxide (9) and crystalline sulphone (8) in ca. 88 and 65percent isolated yield, respectively.When the sulphoxide (9) is heated with dibenzyl L-aspartate in N,N-dimethylacetamide solution at 70-75 deg C for 28 hr, compound (11) is obtained in ca. 70percent isolated yield.Removal of the protecting groups from compound (11) gives N--L-aspartic acid (3) as a crystalline solid in ca. 68percent yield; phosphorylation of compound (11) with dibenzyl phosphorochloridate and removal of the protecting groups gives adenylosuccinic acid (1), isolated as its ammonium salt, in ca. 66percent yield.When the sulphone (8) is converted via compound (11) into the diacids (3) and (1), the products obtained appear to be contaminated with the D-acids (12) and (14), respectively, which are diastereomers of compounds (3) and (1).