61172-40-5

Basic information

• Product Name: 2',5'-oligoadenylate
• Synonyms: 2',5'-oligoadenylate
• CAS NO: 61172-40-5
• Molecular Formula: C30H38N15O19P3
• Molecular Weight: 1005.633103
• Mol File: 61172-40-5.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• Density: 2.48g/cm³
• Refractive Index: 2.013
• CAS DataBase Reference: 2',5'-oligoadenylate(CAS DataBase Reference)
• NIST Chemistry Reference: 2',5'-oligoadenylate(61172-40-5)
• EPA Substance Registry System: 2',5'-oligoadenylate(61172-40-5)

Safety Data

• Hazardous Substances Data: 61172-40-5(Hazardous Substances Data)

Usage

Type of molecule

2',5'-oligoadenylate (2-5A) is a group of small nucleotide polymers.

Production enzyme

2-5A is produced by the enzyme 2',5'-oligoadenylate synthetase.

Trigger

The production of 2-5A is triggered by viral infections.

Role in immunity

2-5A plays a crucial role in the innate immune response against viruses.

Activation of ribonuclease L

2-5A activates the enzyme ribonuclease L (RNase L), which degrades viral RNA and inhibits viral replication.

Activation of protein kinase R

2-5A also activates the protein kinase R (PKR), which further inhibits viral protein synthesis.

Induction of apoptosis

2-5A can induce apoptosis in infected cells, further limiting viral spread.

Regulation

The production of 2-5A is tightly regulated.

Dysregulation consequences

Dysregulation of 2-5A production has been linked to autoimmune diseases and other inflammatory conditions.

Therapeutic implications

2-5A has potential therapeutic implications for managing viral diseases.

InChI:InChI=1/C30H38N15O19P3/c31-22-13-25(37-4-34-22)43(7-40-13)28-19(49)16(46)10(60-28)2-58-66(53,54)64-21-18(48)12(62-30(21)45-9-42-15-24(33)36-6-39-27(15)45)3-59-67(55,56)63-20-17(47)11(1-57-65(50,51)52)61-29(20)44-8-41-14-23(32)35-5-38-26(14)44/h4-12,16-21,28-30,46-49H,1-3H2,(H,53,54)(H,55,56)(H2,31,34,37)(H2,32,35,38)(H2,33,36,39)(H2,50,51,52)/t10?,11-,12-,16-,17-,18-,19-,20?,21-,28?,29-,30-/m1/s1

Upstream product

• 95314-15-1 MopA₂'p5'A₂'p5'A triethylammonium salt 
• 70062-83-8 adenylyl(2'-5')adenylyl(2'-5')adenosine 
• 20816-58-4 adenosine 5'-phosphorimidazolide 
• 95314-00-4 adenosine 5'-phosphoromorpholidate sodium salt 
• 60031-83-6 adenosine 5'-phosphoroimidazolidate sodium salt 
• 81691-36-3 C₈₆H₈₂Cl₂N₁₇O₂₃P₃ 
• 72351-30-5 C₈₆H₉₂Br₃Cl₂N₁₆O₃₀P₃ 

Downstream Products

• 65954-93-0 pppA2'p5'A2'p5'A 
• 76991-64-5 5'-diphosphate of 2',5'-triadenylate 

Relevant articles and documents

Role of the stereochemistry of 3'-fluoro-3'-deoxy analogues of 2-5A in binding to and activation of mouse RNase L

The synthesis of two sets of analogues of 2-5A trimer containing 9-(3-fluoro-3-deoxy-β-D-xylo-furanosyl)adenine (AF) or 3'-fluoro-3'-deoxyadenosine (AF) at different positions of the chain is described, along with the preparation of the corresponding 5'-monophosphates and 5'-diphosphorylated (core) trimers.The ability of each ribo and xylo isomeric pair of fluorodeoxy analogues of 2-5A (i) to compete with p3(A2'p)3A3'pC3'p for binding to RNase L in L929 cell extracts, and (ii) to activate the partially purified RNase L from L929 cell extracts to hydrolyze poly(U), was compared to that of the related 3'-deoxy analogue and the parent trimer, p3A3, using radiobinding and RNase L-(2',5')pentaadenylate(core)-agarose assays, respectively.Evidence is presented to show that the stereochemistry of the trimers plays an important role, specifically in the second process.The most striking observation is that, compared to 2-5A, p3A(AF)A was found to be nine times more effective an activator of RNase L, whereas isomeric p3A(AF)A is 30 times less effective.

Expedient Chemical Synthesis of Sequence-Specific 2',5'-Oligonucleotides

A rapid chemical approach to the preparation of sequence-specific 2',5'-oligonucleotides and analogues of 2-5A is described.For instance, reaction of the 5'-phosphoromorpholidate of adenosine (MopA, 14) with the 5'-phosphoroimidazolidate of inosine (ImpI, 17), under conditions of lead ion catalysis, gave MopA2'p5'I (19a) in 21percent yield.Acid hydrolysis of 19a gave pA2'p5'I, which then was converted to the corresponding 5'-phosphoroimidazolidate Imp5'A2'p5'I (19c) through redox condensation with triphenylphosphine, imidazole, and 2,2-dipyridyl disulfide.Lead ion catalyzed condensation of 19c with Mop5'A (14) gave Mop5'A2'p5'A2'p5'I (30) in 17percent yield.By acid hydrolysis, 30 could be converted to the corresponding 5'-monophosphate, or, by reaction with pyrophosphate in DMF, to the corresponding 2-5A analogue, ppp5'A2'p5'A2'p5'I (5b).The following oligonucleotides were prepared by using similar methodology: ppp5'A2'p5'A2'p5'A (1b), ppp5'A2'p5'I2'p5'A (4b), ppp5'I2'p5'A2'p5'A (3b), and ppp5'A2'p5'A2'p5'(2'dA) (2b).

A new synthetic method for 5'-triphosphoryl-adenylyl-(2'-5')-adenylyl-(2'-5')-adenosine (2-5A) and 2-5A core using 3'-O-tetrahydrofuranyl-adenosine derivatives

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