5-(((Carboxymethyl)amino)methyl)uridine

Base Information

• Chemical Name: 5-(((Carboxymethyl)amino)methyl)uridine
• CAS No.: 69181-26-6
• Molecular Formula: C₁₂H₁₇N₃O₈
• Molecular Weight: 331.282
• DSSTox Substance ID: DTXSID50988889
• Nikkaji Number: J2.191.158E
• Wikidata: Q27133224
• Metabolomics Workbench ID: 63332
• Mol file: 69181-26-6.mol

Synonyms:5-(((carboxymethyl)amino)methyl)uridine;CMAMU

Chemical Property of 5-(((Carboxymethyl)amino)methyl)uridine

Chemical Property:

• PSA: 174.11000
• Density: 1.645g/cm³
• LogP: -3.28680
• XLogP3: -4.7
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 6
• Exact Mass: 331.10156451
• Heavy Atom Count: 23
• Complexity: 536

Purity/Quality:

97% ^*data from raw suppliers

5-Carboxymethylaminomethyluridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C(=O)NC(=O)N1C2C(C(C(O2)CO)O)O)CNCC(=O)O
• Isomeric SMILES: C1=C(C(=O)NC(=O)N1[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)CNCC(=O)O
• Uses: 5-Carboxymethylaminomethyluridine or cmnm5U, is a modification of tRNA responsible for restricting codon-anticodon wobbling and recognition of purine-ending codons. This modification can be catalyzed by the action of GidA and MnmE enzymes on uridine.

Technology Process of 5-(((Carboxymethyl)amino)methyl)uridine

There total 17 articles about 5-(((Carboxymethyl)amino)methyl)uridine 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: 77.0%

5-pivaloyloxymethyluridine + Gly-tetra-n-butyl-ammonium salt (113790-35-5) → 5-carboxymethylaminomethyluridine (69181-26-6)

Guidance literature:

In ethanol; at 60 ℃; for 20h;

DOI:10.1016/j.tetlet.2015.10.023

Reference yield: 75.0%

C17H25N3O9 → 5-carboxymethylaminomethyluridine (69181-26-6)

Guidance literature:

With methylamine; In water; at 60 ℃; for 1h;

DOI:10.1016/j.tetlet.2015.10.023

Reference yield: 70.0%

{[1-((3aR,4R,6R,6aR)-6-Hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-ylmethyl]-amino}-acetic acid tert-butyl ester (89845-85-2) → 5-carboxymethylaminomethyluridine (69181-26-6)

Guidance literature:

With water; trifluoroacetic acid; for 5h; Ambient temperature;

DOI:10.1039/c39840000062

upstream raw materials:

5-<(N-trifluoroacetyl)methoxycarbonylmethylaminomethyl>uridine

{[1-((3aR,4R,6R,6aR)-6-Hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-ylmethyl]-amino}-acetic acid tert-butyl ester

2',3'-O-isopropylidene-5-pyrrolidinomethyluridine

5-chloromethyluridine

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