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D8668

2′-Deoxyadenosine monohydrate

Name: 2′-Deoxyadenosine monohydrate
Brand: SIGMA

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:

16373-93-6

Molecular Weight:

269.26

Beilstein:

91015

EC Number:

213-488-7

MDL number:

MFCD00005754

UNSPSC Code:

12352207

PubChem Substance ID:

24894112

NACRES:

NA.75

biological source

synthetic (organic)

Quality Level

200

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)

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)

Vpx mediated degradation of SAMHD1 has only a very limited effect on lentiviral transduction rate in ex vivo cultured HSPCs

Li D, et al.

Stem Cell Research, 15(2), 271-280 (2015)

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)

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