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D8668

Sigma-Aldrich

2′-Deoxyadenosine monohydrate

powder, BioReagent, suitable for cell culture

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Synonym(s):
9-(2-Deoxy-β-D-ribofuranosyl)adenine, Adenine deoxyriboside
Empirical Formula (Hill Notation):
C10H13N5O3 · H2O
CAS Number:
Molecular Weight:
269.26
Beilstein/REAXYS Number:
91015
EC Number:
MDL number:
UNSPSC Code:
12352207
PubChem Substance ID:
NACRES:
NA.75

biological source

synthetic (organic)

Quality Level

product line

BioReagent

assay

≥99% (HPLC)

form

powder

technique(s)

cell culture | mammalian: suitable

solubility

H2O: soluble 25 mg/mL, clear to slightly hazy, colorless to faintly yellow

storage temp.

2-8°C

SMILES string

[H]O[H].Nc1ncnc2n(cnc12)[C@H]3C[C@H](O)[C@@H](CO)O3

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

InChI key

OLXZPDWKRNYJJZ-RRKCRQDMSA-N

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Application

2′-Deoxyadenosine monohydrate has been used as a nucleotide precursor:
  • To study the importance of homologous recombination at the interface between replication and mitosis
  • To analyze deoxynucleoside-assisted transductions
  • To study the effect of increased deoxycytidine on gemcitabine resistance in pancreatic cancer cells

2′-Deoxyadenosine monohydrate has been used for the preparation of deoxyribonucleoside stock solution for the anaerobic culture of Bacillus mojavensis strains including JF-2 and two Bacillus subtilis strains.

Biochem/physiol Actions

Excess 2′-deoxyadenosine gets converted to adenosine triphosphate (dATP), which inhibits ribonucleotide reductase.

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves


Certificates of Analysis (COA)

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Spontaneous slow replication fork progression elicits mitosis alterations in homologous recombination-deficient mammalian cells
Wilhelm T, et al.
Proceedings of the National Academy of Sciences of the USA, 111(2), 763-768 (2014)
Pharmaceutical Chemistry, International Edition, 430-430 (2011)
Pharmaceutical Chemistry E-Book, 430-430 (2011)
Anaerobic growth of Bacillus mojavensis and Bacillus subtilis requires deoxyribonucleosides or DNA
Folmsbee MJ, et al.
Applied and Environmental Microbiology, 70(9) (2004)
Detection and visualization of protein interactions with protein fragment complementation assays.
I Remy et al.
Methods in molecular biology (Clifton, N.J.), 185, 447-459 (2002-01-05)

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