Uridylyl-(2'-5')-adenosine

Base Information

• Chemical Name: Uridylyl-(2'-5')-adenosine
• CAS No.: 10453-52-8
• Molecular Formula: C19H24 N7 O12 P
• Molecular Weight: 573.413
• DSSTox Substance ID: DTXSID80146531
• Wikidata: Q83011359
• Mol file: 10453-52-8.mol

Synonyms:uridylyl-(2'-5')-adenosine

Chemical Property of Uridylyl-(2'-5')-adenosine

Chemical Property:

• PSA: 289.69000
• Density: 2.23g/cm3
• LogP: -2.67580
• XLogP3: -5.4
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 16
• Rotatable Bond Count: 8
• Exact Mass: 573.12205622
• Heavy Atom Count: 39
• Complexity: 1020

Purity/Quality:

98%,99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CN(C(=O)NC1=O)C2C(C(C(O2)COCC3C(C(C(O3)N4C=NC5=C(N=CN=C54)N)OP(=O)(O)O)O)O)O
• Isomeric SMILES: C1=CN(C(=O)NC1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)COC[C@@H]3[C@H]([C@H]([C@@H](O3)N4C=NC5=C(N=CN=C54)N)OP(=O)(O)O)O)O)O

Technology Process of Uridylyl-(2'-5')-adenosine

There total 3 articles about Uridylyl-(2'-5')-adenosine 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:

5'-adenosine monophosphate (61-19-8,24937-83-5,67583-85-1) → D,D,D-U(3'-5')pA(3'-5')pA (2889-33-0) + phosphoric acid adenosin-5'-yl ester uridin-3'-yl ester (3256-24-4) + D,D-U(2'-5')pA (10453-52-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 2,2'-dipyridyldisulphide; triethylamine; triphenylphosphine / dimethyl sulfoxide; N,N-dimethyl-formamide / 3 h

1.2: 2 h

2.1: Na(+)-montmorillonite / 1 h / 24 °C

2.2: 24 °C

With 2,2'-dipyridyldisulphide; triethylamine; triphenylphosphine; In dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1080/15257770.2012.701787

Reference yield:

adenosine 5'-phosphoroimidazolidate sodium salt (60031-83-6) + uridine (58-96-8) → D,D,D-U(3'-5')pA(3'-5')pA (2889-33-0) + phosphoric acid adenosin-5'-yl ester uridin-3'-yl ester (3256-24-4) + D,D-U(2'-5')pA (10453-52-8)

Guidance literature:

uridine; With Na(+)-montmorillonite; at 24 ℃; for 1h;

adenosine 5'-phosphoroimidazolidate sodium salt; at 24 ℃;

DOI:10.1080/15257770.2012.701787

Reference yield:

UTP (63-39-8) + ATP (56-65-5,896506-78-8) → U2'p5'A2'p5'U (1270047-34-1) + A2'p5'A2'p5'U (97205-06-6) + U2'p5'A2'p5'A (1270047-36-3) + U2'p5'A2'p5'A2'p5'A (1270047-35-2) + A2'p5'A2'p5'A2'p5'U (1270047-37-4) + adenylyl-(2'->5')-adenylyl-(2'->5')-adenylyl-(2'->5')-adenosine (73853-00-6) + D,D-U(2'-5')pA (10453-52-8) + uridylyl-(5'->2')-adenosine (10061-10-6) + adenylyl(3'-5')phosphoadenine (2273-76-9)

Guidance literature:

UTP; ATP; With potassium chloride; magnesium chloride; at 37 ℃; for 17h; pH=8; aq. buffer; Enzymatic reaction;

With shrimp alkaline phosphatase; magnesium chloride; at 37 ℃; for 1h; pH=8; aq. buffer; Enzymatic reaction;

DOI:10.3390/md8020235

upstream raw materials:

UTP

ATP

5'-adenosine monophosphate

adenosine 5'-phosphoroimidazolidate sodium salt

Refernces

• 1、 Lopp, Annika,Reintamm, Tonu,Kuusksalu, Anne,Tammiste, Indrek,Pihlak, Arno,Kelve, Merike. "Natural occurrence of 2′,5′-linked heteronucleotides in marine sponges". experimental part. p. 235 - 254. Retrieved 2010/10/19.