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D8668

Sigma-Aldrich

2′-Deoxyadenosine monohydrate

powder, BioReagent, suitable for cell culture

Synonym(s):

9-(2-Deoxy-β-D-ribofuranosyl)adenine, Adenine deoxyriboside

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About This Item

Empirical Formula (Hill Notation):
C10H13N5O3 · H2O
CAS Number:
Molecular Weight:
269.26
Beilstein:
91015
EC Number:
MDL number:
UNSPSC Code:
12352207
PubChem Substance ID:
NACRES:
NA.75

biological source

synthetic (organic)

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.

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
MUC1 and HIF-1alpha signaling crosstalk induces anabolic glucose metabolism to impart gemcitabine resistance to pancreatic cancer
Shukla S, et al.
Cancer Cell, 32(1), 71-87 (2017)
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)

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