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

Uses

Different sources of media describe the Uses of 4542-23-8 differently. You can refer to the following data:
1. Succinyladenosine (S-Ado) is a biochemical marker of adenylosuccinase deficiency - the genetic defect of purine de novo synthesis. ?S-Ado has been previously reported as normally undetectable in cerebrospinal fluid (CSF) of children not suffering from thi
2. Succinyladenosine (S-Ado) is a biochemical marker of adenylosuccinase deficiency - the genetic defect of purine de novo synthesis. ?S-Ado has been previously reported as normally undetectable in cerebrospinal fluid (CSF) of children not suffering from this defect.

Definition

ChEBI: An aspartic acid derivative that is L-aspartic acid in which one of the amine hydrogens is substituted by a 9-beta-D-ribofuranosyl-9H-purin-6-yl group.

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

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

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).