2'-Deoxyadenosine monohydrate

2'-Deoxyadenosine monohydrate Basic information
Product Name:2'-Deoxyadenosine monohydrate
Synonyms:DEOXYADENOSINE HYDRATE;ADENINE DEOXYRIBOSIDE;ADENINE DEOXYRIBOSIDE HYDRATE;ADENINE DEOXYRIBOSIDE MONOHYDRATE;9-(2-DEOXY-BETA-D-RIBOFURANOSYL)ADENINE;9-(2-DEOXY-BETA-D-RIBOFURANOSYL)ADENINE MONOHYDRATE;2'-DEOXYADENOSINE HYDRATE;2'-DEOXYADENOSINE MONOHYDRATE
CAS:16373-93-6
MF:C10H15N5O4
MW:269.26
EINECS:683-408-7
Product Categories:Inhibitors;Bases & Related Reagents;Intermediates & Fine Chemicals;Nucleotides;Pharmaceuticals;Biochemistry;Nucleosides and their analogs;Nucleosides, Nucleotides & Related Reagents
Mol File:16373-93-6.mol
2'-Deoxyadenosine monohydrate Structure
2'-Deoxyadenosine monohydrate Chemical Properties
Melting point 187-189 °C
refractive index -25.5 ° (C=0.5, H2O)
storage temp. 2-8°C
solubility H2O: soluble50mg/mL, clear, colorless
form powder
color White to light beige
Water Solubility 0.3 g/100 mL (20 ºC)
BRN 5191174
Stability:Stable, but air sensitive. Incompatible with strong oxidizing agents.
InChIKeyWZJWHIMNXWKNTO-VWZUFWLJSA-N
CAS DataBase Reference16373-93-6(CAS DataBase Reference)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 22-36/37/38-20/21/22
Safety Statements 24/25-37/39-36-26
RIDADR UN2811 6.1/PG 3
WGK Germany 3
RTECS AU7358600
10-23
TSCA Yes
HS Code 29349990
MSDS Information
ProviderLanguage
ACROS English
ALFA English
2'-Deoxyadenosine monohydrate Usage And Synthesis
Description2'-Deoxyadenosine monohydrate is an adenosine nucleotide, which can be synthesized by the enzyme adenosine kinase. 2'-Deoxyadenosine monohydrate is a competitive inhibitor of phosphodiesterase, which breaks down cyclic nucleotides to their corresponding monophosphate form. This leads to elevated levels of cAMP, which can cause neuronal death by apoptosis.
Chemical PropertiesWhite crystalline powder
Uses2'-Deoxyadenosineise is used by some cells as an energy source under energy stress conditions and to affect cAMP levels. 2'-dAdo is used in comparison studies of the functions of adenosine analogues on various biological processes.
Uses2′-Deoxyadenosine monohydrate has been used:
  • as a component for nucleoside supplementation
  • as a standard for to estimate DNA global methylation rate in proliferating oil palm embryogenic suspensions
  • to reverse sterile alpha motif (SAM) and histidine-aspartate (HD) domain-containing protein (SAMHD1)
  • inhibition of human immunodeficiency virus (HIV-1) and hepatitis B virus (HBV)

Uses2'-Deoxyadenosine monohydrate is used in the synthesis of 5'-modified 2'-deoxyadenosine analogues as anti-hepatitis C virus agents.
Biochem/physiol ActionsExcess 2′-deoxyadenosine gets converted to adenosine triphosphate (dATP), which inhibits ribonucleotide reductase.
Purification MethodsPurify it by recrystallisation from H2O (hydrated crystals; solubility of the monohydrate is 1.1% in H2O at 20o). It has max 258nm (pH 1), 260nm (pH 7) and 261nm (pH 13). [Ness & Fletcher J Am Chem Soc 81 4752 1959, Walker & Butler Can J Chem 34 1168 1956.] The 3',5'-O-diacetyl derivative has m 151-152o (from EtOAc/pet ether). [Beilstein 26 III/IV 3589.]
2'-Deoxyadenosine monohydrate Preparation Products And Raw materials
5'-Tosyladenosine [5'-13C]2'-DEOXYADENOSINE MONOHYDRATE N6,N6-DIMETHYLADENOSINE [5',5''-2H2]2'-DEOXYADENOSINE MONOHYDRATE [2'-13C]2'-DEOXYADENOSINE MONOHYDRATE 5'-ACETYL-2',3'-ISOPROPYLIDENEADENOSINE 5'-CHLORO-5'-DEOXYADENOSINE MONOHYDRATE ADENOSINE 5'-TRIPHOSPHATASE [1'-13C]2'-DEOXYADENOSINE MONOHYDRATE 3'-ADENYLIC ACID 2',3',5'-TRI-O-ACETYL-8-BROMOADENOSINE [1'-2H]2'-DEOXYADENOSINE MONOHYDRATE N6-ISOPENTENYLADENOSINE-D6 Adenosine 5'-monophosphate monohydrate N6-Benzoyl-2'-deoxyadenosine [1',2',3',4',5'-13C5]2'-DEOXYADENOSINE MONOHYDRATE 6-METHYLAMINOPURINE 9-RIBOFURANOSIDE 2'-Deoxyadenosine 5'-phosphate

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