19341-57-2

Basic information

• Product Name: ADENOSINE 5'-O-THIOMONOPHOSPHATE DILITHIUM SALT
• Synonyms: 5'-AMPS 2 LI;ADENOSINE 5'-O-THIOMONOPHOSPHATE DILITHIUM SALT;AMP-S DILITHIUM SALT;Adenosine 5'-thiophosphate;Adensine 5'-o-thiomonophosphate dilithium salt;adenosine 5'-phosphorothioate;adenosine 5'-[alpha-thio]monophosphate dilithium salt
• CAS NO: 19341-57-2
• Molecular Formula: C₁₀H₁₄N₅O₆PS
• Molecular Weight: 375.15
• Mol File: 19341-57-2.mol

Chemical Properties

• Boiling Point: 785.1°Cat760mmHg
• Flash Point: 428.6°C
• Appearance: /
• Density: 2.25g/cm³
• Storage Temp.: −20°C
• PKA: 1.11±0.50(Predicted)
• CAS DataBase Reference: ADENOSINE 5'-O-THIOMONOPHOSPHATE DILITHIUM SALT(CAS DataBase Reference)
• NIST Chemistry Reference: ADENOSINE 5'-O-THIOMONOPHOSPHATE DILITHIUM SALT(19341-57-2)
• EPA Substance Registry System: ADENOSINE 5'-O-THIOMONOPHOSPHATE DILITHIUM SALT(19341-57-2)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36
• Safety Statements: 26-36/37/39-45-7/9
• WGK Germany: 1
• Hazardous Substances Data: 19341-57-2(Hazardous Substances Data)

Usage

Purification Methods

Purify it as for the diNa salt [Murray & Atkinson Biochemistry 7 4023 1968]. Dissolve 0.3g in dry MeOH (7mL) and 1M LiI (6mL) in dry Me2CO containing 1% of mercaptoethanol, and the Li salt is precipitated by adding Me2CO (75mL). The residue is washed with Me2CO (4 x 30mL) and dried at 55o/25mm. UV: max (HCl, pH 1.2) 257nm ( 14,800); (0.015M NaOAc, pH 4.8) 259nm ( 14,800); and (0.015 4OH, pH 10.1) 259nm ( 15,300).

Upstream product

• 13241-24-2 2',3'-O-ethoxymethylene-N⁶-dimethylaminomethyleneadenosine 
• 58-61-7 adenosine 
• 362-75-4 2',3'-isopropylidene adenosine 

Downstream Products

• 58976-48-0 (S_P)-Adenosine-5'-O-(1-Thiotriphosphate) 
• 58976-48-0 Adenosine 5'<(S)α-thio>triphosphate 
• 58976-49-1 (R_p)-adenosine 5'-O-(1-thiotriphosphate) 
• 59331-71-4 (Rp)-adenosine 5'-(1-thiodiphosphate) 
• 61-19-8 5'-adenosine monophosphate 

Relevant articles and documents

Synthesis ofnucleoside 3'-thiophosphates in one step procedure

A mild and efficient one-step method of thiophosphorylation was devised for acid-sensitive nucleosides. The procedure is based on thiophosphorylation of nucleoside magnesium alkoxide by 2-chloro-2-thio-l,3,2-dioxaphospholane. The utility and efficiency of this method combined with deprotection of the resulting cyclic triester were demonstrated by its application to the synthesis of both adenosine 3'- and 5'thiophosphates. The procedure does not require protection of the exocyclic amino group and can be successfully used for the thiophosphorylation of nucleosides that are unusually sensitive to depurination. Copyright 1999 by Marcel Dekker, Inc.

Acid-catalysed hydrolysis of adenosine 5′-phosphorodithiomorpholidate

Adenosine 5′-phosphorodithiomorpholidate 1c is quantitatively converted into adenosine 5 within 1 hr in acetic acid - water (95:5 v/v) solution at room temperature.

Polymer-bound oxathiaphospholane: A solid-phase reagent for regioselective monothiophosphorylation and monophosphorylation of unprotected nucleosides and carbohydrates

(Chemical Equation Presented) Two polymers bound to N,N-diisopropylamino-1, 3,2-oxathiaphospholane were reacted with unprotected carbohydrates and nucleosides in the presence of 1H-tetrazole, followed by oxidation with tert-butyl hydroperoxide or sulfurization with Beaucage's reagent. The 1,3,2-oxathiaphospholane ring-opening with 3-hydroxypropionitrile, followed by treatment with DBU, afforded the corresponding monophosphate and monothiophosphate derivatives, respectively, through the elimination of polymer-bound ethylene episulfide. Reactions using this strategy offer the advantages of high regioselectivity, monosubstitution, and facile isolation and recovery of products.

PREPARATION OF DERIVATIVES OF INOSINE 5'-PHOSPHOROTHIOATE FOR USE IN AFFINITY CHROMATOGRAPHY

In the paper the known methods of preparation of ribonucleoside 5'-phosphorothioates II are evaluated and an improved method of their synthesis is described, based on the reaction of 2',3'-O-ethoxymethyleneribonucleosides III with thiophosphoryl chloride in the presence of one equivalent of pyridine, and subsequent hydrolysis.Inosine 5'-phosphate and inosine 5'-phosphorothioate (IIc) were converted to 2',3'-O-cyclic ketals of levulinic acid Vb, VIb on reaction with ethyl levulinate and ethyl orthoformate and subsequent alkaline hydrolysis.O-(4-Aminophenyl)inosine 5'-phosphorothioate (IX) was prepared from 2',3'-O-isopropylideneinosine (VII) with O-(4-nitrophenyl)thiophosphoryldiimidazolide and subsequent catalytic hydrogenation of the O-(4-nitrophenyl) ester VIII formed.