2'-Deoxyadenosine Chemical Properties

Melting point:

187-189 °C

Boiling point:

394.4°C (rough estimate)

Density 

1.2938 (rough estimate)

refractive index 

1.7610 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

solubility 

DMSO (Slightly), Methanol (Slightly), Water (Slightly)

form 

powder

pka

pK1:3.8(+1) (25°C,μ=0.1)

color 

White

PH

3.8

Water Solubility 

Soluble in water and caustic soda.

λmax

258 (pH 2)；260 (pH 7)

Stability:

Hygroscopic

InChI

InChI=1S/C10H13N5O3/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(17)6(2-16)18-7/h3-7,16-17H,1-2H2,(H2,11,12,13)/t5-,6+,7+/m0/s1

InChIKey

OLXZPDWKRNYJJZ-RRKCRQDMSA-N

SMILES

OC[C@H]1O[C@@H](N2C3C(=C(N=CN=3)N)N=C2)C[C@@H]1O

CAS DataBase Reference

958-09-8(CAS DataBase Reference)

NIST Chemistry Reference

Deoxyadenosine(958-09-8)

EPA Substance Registry System

Adenosine, 2'-deoxy- (958-09-8)

Safety Information

RIDADR 

2811

WGK Germany 

3

RTECS 

AU7358600

F 

10-23

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

Ⅲ

HS Code 

2934999090

MSDS

• Language:English Provider:SigmaAldrich

2'-Deoxyadenosine Usage And Synthesis

Description

2'-Deoxyadenosine is a natural deoxyribonucleoside, which is a structural fragment of deoxyribonucleic acid DNA. It is a purine nucleoside component of DNA comprised of adenosine linked by its N9 nitrogen to the C1 carbon of deoxyribose. Like other natural nucleosides, it is involved in the transmission of genetic information in almost all biological cells, affecting protein synthesis and polysaccharide. It plays a very important role in regulating the growth, proliferation, differentiation and inhibition of cells in vivo.

Uses

2'-Deoxyadenosine is used in paradoxical stimulation study of human sperm motility. It plays an essential role as sperm motility stimulants used in sperm micro-injection on mouse and human embryo development. It finds an application in some cells as an energy source under energy stress conditions. It is involved in various biological processes to compare the functions of adenosine analogues.

Definition

ChEBI: 2'-deoxyadenosine is a purine 2'-deoxyribonucleoside having adenine as the nucleobase. It has a role as a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is a purines 2'-deoxy-D-ribonucleoside and a purine 2'-deoxyribonucleoside.

Preparation

2'-deoxyadenosine synthesis: esterification of adenosine, acylation of an acylating agent and an acid binding agent to obtain an acylate; the obtained acylate is then subjected to reduction and purification to obtain 2'-deoxyadenosine. The esterification agent used in the esterification process is dialkyl tin oxide, 2'-O-p-toluenesulfonyladenosine is synthesized from adenosine, and 2'-deoxyadenosine is synthesized from 2'-O-p-toluenesulfonyladenosine glycosides.

Biological Functions

2'-Deoxyadenosine (Deoxyadenosine) is a critical component of DNA. When present in sufficiently high levels, deoxyadensoine can act as an immunotoxin and a metabotoxin. An immunotoxin disrupts, limits the function, or destroys immune cells. A metabotoxin is an endogenous metabolite that causes adverse health effects at chronically high levels.

Biological Activity

2'-Deoxyadenosine is a deoxyribonucleoside and an intermediate in the purine nucleotide degradation pathway. It is transported into cells via facilitated diffusion or formed within cells by degradation of S-adenosylhomocysteine or AMP and is removed from cells by purine metabolism or is converted into adenine nucleotides. 2'-Deoxyadenosine has been used in the characterization of DNA conformations and the synthesis of nucleoside analogs as antiviral agents.

Source

2'-Deoxyadenosine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). 2'-Deoxyadenosine is a natural product found in Streptomyces jiujiangensis, Fritillaria przewalskii, and other organisms with data available.

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