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Merck
CN

30957

Sigma-Aldrich

2-Deoxy-D-ribono-1,4-lactone

≥95% (GC)

Synonym(s):

(4S,5R)-4-Hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one, 2-Deoxy-D-ribonic acid γ-lactone

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About This Item

Empirical Formula (Hill Notation):
C5H8O4
CAS Number:
34371-14-7
Molecular Weight:
132.11
Beilstein:
81260
MDL number:
MFCD15144952
UNSPSC Code:
12352201
PubChem Substance ID:
329753608
NACRES:
NA.25

Key Documents

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Assay

≥95% (GC)

optical activity

[α]/D 19.0±2.5°, c = 1 in H2O

suitability

conforms to structure for Proton NMR spectrum

storage temp.

−20°C

SMILES string

O[C@H]1CC(O[C@@H]1CO)=O

InChI

1S/C5H8O4/c6-2-4-3(7)1-5(8)9-4/h3-4,6-7H,1-2H2/t3-,4+/m0/s1

InChI key

YIXDEYPPAGPYDP-IUYQGCFVSA-N

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCBM1791V
BCBM1791

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Bruce Demple et al.
DNA repair, 4(12), 1442-1449 (2005-10-04)
Many oxidative DNA lesions are handled well by base excision repair (BER), but some types may be problematic. Recent work indicates that 2-deoxyribonolactone (dL) is such a lesion by forming stable, covalent cross-links between the abasic residue and DNA repair
Marc M Greenberg
Organic & biomolecular chemistry, 5(1), 18-30 (2006-12-14)
DNA damage is a double-edged sword. The modifications produced in the biopolymer are associated with aging, and give rise to a variety of diseases, including cancer. DNA is also the target of anti-tumor agents and the most generally used nonsurgical
2-Deoxyribonolactone lesions in X-ray-irradiated DNA: quantitative determination by catalytic 5-methylene-2-furanone release.
Marina Roginskaya et al.
Angewandte Chemie (International ed. in English), 44(38), 6210-6213 (2005-09-02)
Haidong Huang et al.
The Journal of organic chemistry, 73(7), 2695-2703 (2008-03-08)
DNA damage results in the formation of abasic sites from the formal hydrolysis of the glycosidic bond (AP) and several oxidized abasic lesions. Previous studies on AP sites revealed that DNA polymerases preferentially incorporated dA opposite them in approximately 80%
Haidong Huang et al.
Journal of the American Chemical Society, 130(19), 6080-6081 (2008-04-17)
The ability of DNA polymerases to maintain the integrity of the genome even after it has been structurally altered is vital. There is considerable interest in determining the structural properties of the DNA template that polymerases recognize when determining which
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