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31170

Sigma-Aldrich

2-Deoxy-D-ribose

≥99.0% (TLC)

Synonym(s):

2-Deoxy-D-arabinose, 2-Deoxy-D-erythropentose, Thyminose

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About This Item

Empirical Formula (Hill Notation):
C5H10O4
CAS Number:
533-67-5
Molecular Weight:
134.13
Beilstein:
1721978
EC Number:
208-573-0
MDL number:
MFCD00135904
UNSPSC Code:
12352201
PubChem Substance ID:
57648512
NACRES:
NA.25

Assay

≥99.0% (TLC)

form

solid

optical activity

[α]20/D −56±2°, 24 hr, c = 1% in H2O

impurities

<0.5% Sulphated ash

ign. residue

≤0.5% (as SO4)

loss

≤1% loss on drying, 20 °C (HV)

color

white

mp

89-90 °C (lit.)

solubility

water: 50 mg/mL, clear, colorless to faintly yellow

storage temp.

2-8°C

SMILES string

OC[C@@H](O)[C@@H](O)CC=O

InChI

1S/C5H10O4/c6-2-1-4(8)5(9)3-7/h2,4-5,7-9H,1,3H2/t4-,5+/m0/s1

InChI key

ASJSAQIRZKANQN-CRCLSJGQSA-N

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Application

2-Deoxy-D-ribose is used to study processes of oxidative stress and glycation in vivo and in vitro. 2-Deoxy-D-ribose, an endothelial-cell chemoattractant and angiogenesis-inducing factor, is used to study processes of tumor angiogenesis and progression mediated at the level of thymidine phosphorylase activity.

Other Notes

To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Guillaume Mata et al.
The Journal of organic chemistry, 77(20), 9006-9017 (2012-09-15)
An efficient method for the N-2-deoxyribosylation of modified nucleobases by 2-deoxythioriboside donors is reported. In the presence of an in situ silylated nucleobase, thioglycosides can be activated with NIS/HOTf to give nucleosides in high yields and with good β-selectivity. By
N S Brown et al.
The Biochemical journal, 334 ( Pt 1), 1-8 (1998-08-07)
Angiogenesis is the term used to describe the formation of new blood vessels from the existing vasculature. In order to attract new vessels, a tissue must release an endothelial-cell chemoattractant. 2-Deoxy-D-ribose is produced in vivo by the catalytic action of
Kazumi Taniho et al.
Bioorganic & medicinal chemistry letters, 22(7), 2518-2521 (2012-03-02)
To elucidate the role of the sugar moiety in the two natural nucleotides of the 3'-overhang region of small interfering RNA (siRNA), we synthesized siRNAs that incorporated two abasic nucleosides, 1-deoxy-D-ribofuranose (R(H)). We improved the method for preparing an O-protected
Katarzyna Lamparska et al.
Nucleic acids research, 40(19), 9788-9801 (2012-08-02)
5-Aza-2'-deoxycytidine (5azaC-dR) has been employed as an inhibitor of DNA methylation, a chemotherapeutic agent, a clastogen, a mutagen, an inducer of fragile sites and a carcinogen. However, its effects are difficult to quantify because it rapidly breaks down in aqueous
Manuel Ellermann et al.
Acta crystallographica. Section D, Biological crystallography, 68(Pt 3), 253-260 (2012-02-22)
The biological activity of catechol neurotransmitters such as dopamine in the synapse is modulated by transporters and enzymes. Catechol-O-methyltransferase (COMT; EC 2.1.1.6) inactivates neurotransmitters by catalyzing the transfer of a methyl group from S-adenosylmethionine to catechols in the presence of
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