103659-66-1

Basic information

• Product Name: bis(tri-n-butylammonium) pyrophosphate
• CAS NO: 103659-66-1
• Molecular Weight: 548.681
• Mol File: 103659-66-1.mol

Chemical Properties

• CAS DataBase Reference: bis(tri-n-butylammonium) pyrophosphate(CAS DataBase Reference)
• NIST Chemistry Reference: bis(tri-n-butylammonium) pyrophosphate(103659-66-1)
• EPA Substance Registry System: bis(tri-n-butylammonium) pyrophosphate(103659-66-1)

Safety Data

• Hazardous Substances Data: 103659-66-1(Hazardous Substances Data)

Upstream product

• 102-82-9 tributyl-amine 
• 86119-84-8 phosphoric acid 

Downstream Products

• 90015-82-0 5-[3-aminoallyl]-2'-deoxy-uridine 5'-triphosphate 
• 79551-89-6 L(-)FMAUTP 
• 35542-01-9 5-methoxycarbonylmethyl-2'-O-methyl-uridine 
• 138284-89-6 (1R,4S)-2-Amino-1,9-dihydro-9-<4-(hydroxymethyl)cyclopent-2-enyl>purin-6-one Triphosphate 

Relevant articles and documents

Synthesis of 8-oxo-dGTP and its β,γ-CH2-, β,γ-CHF-, and β,γ-CF2- analogues

Three novel bisphosphonate analogues of 8-oxo-dGTP 3 in which the bridging β,γ-oxygen is replaced by a methylene, fluoromethylene or difluoromethylene group (4–6, respectively) have been synthesized from 8-oxo-dGMP 2 by reaction of its morpholine 5′-phosphoramidate 14 or preferably, its N-methylimidazole 5′-phosphoramidate 15 with tri-n-butylammonium salts of the appropriate bisphosphonic acids, 11–13. The latter method also provides a convenient new route to 3. Analogues 4–6 may be useful as mechanistic probes for the role of 3 in abnormal DNA replication and repair.

Solid-phase synthesis of oligonucleotide 5a?2-(?±-P-Thio)triphosphates and 5a?2-(?±-P-Thio)(?2,?3-methylene)triphosphates

A robust solid-phase synthesis was developed to obtain original oligonucleotides (ONs) functionalized at their 5a?2 end with modified triphosphate (TP) moieties, in which a nonbridging oxygen atom of the ?± phosphorus atom was replaced by a sulfur atom and the labile P-O-P linkage was changed into a methylene bridge between the ?2 and ?3 phosphorus atoms. The efficient method is based on solid-supported ON assembly followed by 5a?2-H-phosphonylation, oxidation to the thiophosphate subsequently activated as a phosphoanhydride with diphenyl phosphoryl chloride, then nucleophilic substitution with the alkylammonium salt of pyrophosphate or its ?2,?3-methylene analogue. After deprotection and release from the solid support under basic conditions, 5a?2-(?±-P-thio)-TP and 5a?2-(?±-P-thio)(?2,?3-methylene)TP oligonucleotides were obtained in satisfactory yields, and they were isolated with high purity. These hydrolysis-resistant 5a?2-TP ONs will be useful in biological research to elucidate the mechanism of enzymes involved in mRNA processing and maturation.

Synthesis and anti-HIV activity of a series of 6-modified 2′,3′-dideoxyguanosine and 2′,3′-didehydro-2′, 3′-dideoxyguanosine analogs

In search of potential 2′,3′-dideoxyguanosine (ddG) and 2′,3′-didehydro-2′,3′-dideoxyguanosine (D4G) prodrugs, a series of 6-modified ddG, D4G analogs were synthesized and evaluated for their anti-HIV activities and cytotoxities in cell-based assays. All analogs showed low cytotoxicities and some of them displayed benign anti-HIV activities. The active triphosphate forms in vivo, ddGTP and D4TTP, were also synthesized by a novel and facile one-pot method. The recognition of ddGTP and D4TTP by Taq, Therminater DNA polymerase and HIV reverse transcriptase (RT) incorporated in DNA/RNA strands were investigated by a non-radioactivity method and K m were determined. A series of 6-modified 2′,3′- dideoxyguanosine and 2′,3′-didehydro-2′,3′- dideoxyguanosine analogs were synthesized. Anti-HIV activity was investigated in cell-based assay. ddGTP was synthesized as well as D4TTP by a novel one-pot method, and the incorporation efficiencies recognized by DNA polymerase and HIV reverse transcriptase (HIV RT) were evaluated. Copyright

Efficient solid-phase chemical synthesis of 5′-triphosphates of DNA, RNA, and their analogues

A robust, reproducible, and scalable method for the solid-phase synthesis of 5′-triphosphates of DNA, RNA, and their chemically modified analogues using 5′-H-phosphonate intermediates is described. 5′-Triphosphates of oligonucleotides with varying lengths

Synthesis of uracil nucleotide analogs with a modified, acyclic ribose moiety as P2Y2 receptor antagonists

A series of new uracil nucleotide analogs (monophosphates, triphosphates, and phosphonates) was synthesized, in which the ribose moiety was replaced by acyclic chains, including branched or linear alkyl or dialkylether linkers. 1-ω-Bromoalkyluracil deriva

Aptamer-based proximity labeling guides covalent RNA modification

We describe the development of a proximity-induced bio-orthogonal inverse electron demand Diels-Alder reaction that exploits the high-affinity interaction between a dienophile-modified RhoBAST aptamer and its tetramethyl rhodamine methyltetrazine substrate. We applied this concept for covalent RNA labeling in proof-of-principle experiments.

Preparation method of P,P-di(uridine 5'-)tetraphosphate

The invention relates to a preparation method of P,P-di(uridine 5'-)tetraphosphate. The method comprises the following steps: under the action of a metal salt catalyst, imidazole triethylamine pyrophosphate shown in formula I and uridine monophosphate triethylamine salt shown in formula II react in N,N-dimethylformamide, and P,P-di(uridine 5'-)tetraphosphate shown in formula III is obtained.

Debranchase-resistant labeling of RNA using the 10DM24 deoxyribozyme and fluorescent modified nucleotides

The 10DM24 deoxyribozyme can site-specifically label RNAs with fluorophore-GTP conjugates; however, the 2′,5′-branched RNA linkage is readily cleaved by debranchase. To prevent loss of labels upon cleavage, we synthesized phosphorothioate-modified, fluore

Method of preparing phosphate

The invention provides a method of preparing a phosphate. The method comprises the following step: enabling a pyrophosphate active compound expressed by formula II to react with uridine monophosphate expressed by a formula III or a salt thereof in a hydrophilic solvent under the action of a bimetallic ion composite catalyst to obtain P1,P4-bis (5'-uridine group) tetraphosphate expressed by formula I. In the formula II, X is imidazolyl, N-methyl imidazolyl, or 1, 2, 4-triazolyl; and the bimetallic ions in the bimetallic ion composite catalyst are a combination of any two of Zn2+, Mn2+, Mg2+, Fe2+, Fe3+ and Al3+. The method of preparing a phosphate employs a bimetallic catalytic system and can achieve high-efficiency and easy separation preparation of diquafosol.

4-Alkyloxyimino-cytosine nucleotides: Tethering approaches to molecular probes for the P2Y6 receptor

4-Alkyloxyimino derivatives of pyrimidine nucleotides display high potency as agonists of certain G protein-coupled P2Y receptors (P2YRs). In an effort to functionalize a P2Y6R agonist for fluorescent labeling, we probed two positions (N4 and γ-phosphate of cytidine derivatives) with various functional groups, including alkynes for click chemistry. Functionalization of extended imino substituents at the 4 position of the pyrimidine nucleobase of CDP preserved P2Y6R potency generally better than γ-phosphoester formation in CTP derivatives. Fluorescent Alexa Fluor 488 conjugate 16 activated the human P2Y6R expressed in 1321N1 human astrocytoma cells with an EC50 of 9 nM, and exhibited high selectivity for this receptor over other uridine nucleotide-activated P2Y receptors. Flow cytometry detected specific labeling with 16 to P2Y 6R-expressing but not to wild-type 1321N1 cells. Additionally, confocal microscopy indicated both internalized 16 (t1/2 of 18 min) and surface-bound fluorescence. Known P2Y6R ligands inhibited labeling. Theoretical docking of 16 to a homology model of the P2Y6R predicted electrostatic interactions between the fluorophore and extracellular portion of TM3. Thus, we have identified the N4-benzyloxy group as a structurally permissive site for synthesis of functionalized congeners leading to high affinity molecular probes for studying the P2Y6R.