Saicar

Base Information

• Chemical Name: Saicar
• CAS No.: 3031-95-6
• Molecular Formula: C13H19 N4 O12 P
• Molecular Weight: 454.287
• UNII: K1PVR64RIF
• DSSTox Substance ID: DTXSID90184404
• Nikkaji Number: J7.666J
• Wikipedia: Phosphoribosylaminoimidazolesuccinocarboxamide
• Wikidata: Q3502778
• Metabolomics Workbench ID: 37432
• Mol file: 3031-95-6.mol

Synonyms:5'-phosphoribosyl-4-(N-succinylcarboxamide)-5-aminoimidazole;5-amino-4-imidazole-N-succinocarboxamide ribonucleotide;N-(5-amino-1-beta-D-ribofuranosylimidazole-4-carbonyl)-L-aspartic acid 5'-phosphate;SAICAR;SAICAR, (D)-isomer;succinyl-AICAR

Chemical Property of Saicar

Chemical Property:

• Boiling Point: °Cat760mmHg
• PKA: 1.86±0.10(Predicted)
• Flash Point: °C
• PSA: 277.29000
• Density: 2.18g/cm³
• LogP: -1.99250
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Methanol (Slightly), Water (Slightly)
• XLogP3: -4.3
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 9
• Exact Mass: 454.07370905
• Heavy Atom Count: 30
• Complexity: 718

Purity/Quality:

99%, ^*data from raw suppliers

N-Succinyl-5-aminoimidazole-4-carboxamideRibose5’-Phosphate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC(=C(N1C2C(C(C(O2)COP(=O)(O)O)O)O)N)C(=O)NC(CC(=O)O)C(=O)O
• Isomeric SMILES: C1=NC(=C(N1[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)O)O)O)N)C(=O)N[C@@H](CC(=O)O)C(=O)O
• Uses: N-Succinyl-5-aminoimidazole-4-carboxamide Ribose 5’-Phosphate is a metabolite of Purine. Since adenosine is a potent inhibitor of neuronal function, depressing the release of several excitatory transmitters and causing direct hyperpolarization of neurons, it was possible that the symptoms seen in adenylosuccinate lyase (ASase) deficient patients could reflect an interference of succinylpurines with neurotransmission.

Technology Process of Saicar

There total 13 articles about Saicar 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: 96.0%

dibenzyl 5-amino-(1-[5-(((bis(benzyloxy)phosphoryl)oxy)methyl)-3,4-dihydroxytetrahydrofuran-2-yl]-1H-imidazole-4-carbonyl)-L-aspartate → (5-amino-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-((phosphonooxy)methyl)tetrahydrofuran-2-yl)-1H-imidazole-4-carbonyl)-L-aspartic acid (3031-95-6)

Guidance literature:

With 10 wt% Pd(OH)2 on carbon; hydrogen; In methanol; at -2 - 25 ℃; Temperature;

Reference yield:

L-Aspartic acid (56-84-8,25608-40-6,27881-03-4,32505-46-7,52526-39-3) → (5-amino-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-((phosphonooxy)methyl)tetrahydrofuran-2-yl)-1H-imidazole-4-carbonyl)-L-aspartic acid (3031-95-6)

Guidance literature:

With enzymeextracts from chicken liver; sodium hydrogencarbonate; ATP;

Reference yield:

5-Amino-1-((3aR,4R,6R,6aR)-6-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-1H-imidazole-4-carboxylic acid amide (3676-69-5) → (5-amino-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-((phosphonooxy)methyl)tetrahydrofuran-2-yl)-1H-imidazole-4-carbonyl)-L-aspartic acid (3031-95-6)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium hydroxide / 12 h / Inert atmosphere; Reflux

2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / chloroform / 2 h / 25 °C / Inert atmosphere

3: sodium hydride / tetrahydrofuran / 0.83 h / -3 - -2 °C / Inert atmosphere

4: hydrogenchloride; water / tetrahydrofuran / 2 h / 25 °C / Inert atmosphere

5: 10 wt% Pd(OH)2 on carbon; hydrogen / methanol / -2 - 25 °C

With hydrogenchloride; 10 wt% Pd(OH)2 on carbon; water; hydrogen; sodium hydride; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; sodium hydroxide; In tetrahydrofuran; methanol; chloroform;

upstream raw materials:

L-Aspartic acid

5-amino-4-carboxylic acid-1H-imidazol-1-yl ribotide

5-Amino-1-((3aR,4R,6R,6aR)-6-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-1H-imidazole-4-carboxylic acid amide

2',3',5'-tri-O-acetylinosine

Refernces