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Key Documents

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D7400

Sigma-Aldrich

2′-Deoxyadenosine monohydrate

≥99%

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C10H13N5O3 · H2O
Número de CAS:
16373-93-6
Peso molecular:
269.26
Beilstein/REAXYS Number:
91015
EC Number:
213-488-7
MDL number:
MFCD00005754
UNSPSC Code:
41106305
PubChem Substance ID:
24894129
NACRES:
NA.51

biological source

synthetic (organic)

assay

≥99%

form

powder

solubility

water: 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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Categorías relacionadas

Application

2′-Deoxyadenosine monohydrate has been used:
  • as a component for nucleoside supplementation
  • as a standard for to estimate DNA global methylation rate in proliferating oil palm embryogenic suspensions
  • to reverse sterile alpha motif (SAM) and histidine-aspartate (HD) domain-containing protein (SAMHD1)
  • inhibition of human immunodeficiency virus (HIV-1) and hepatitis B virus (HBV)

Biochem/physiol Actions

2′-Deoxyadenosine (2′-dAdo), a deoxyribonucleoside, may be used by some cells as an energy source under energy stress conditions and to affect cAMP levels. 2′-dAdo is used in comparison studies of the functions of adenosine analogues on various biological processes.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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M Nakamura et al.
The Journal of biological chemistry, 257(23), 13945-13950 (1982-12-10)
Regulation of glucose metabolism in glycolysis by round spermatids was studied. Assay of activities of 11 glycolytic enzymes in cell-free spermatid extracts showed that hexokinase, phosphofructokinase, and glyceraldehyde-3-phosphate dehydrogenase had the lowest activities. When the cells were incubated with glucose
Don E Farthing et al.
Scientific reports, 7(1), 4043-4043 (2017-06-24)
Deuterated water (
SAMHD1 Modulates Early Steps during Human Cytomegalovirus Infection by Limiting NF-kappaB Activation
Kim ET, et al.
Testing, 28(2), 434-448 (2019)
O Magnus et al.
International journal of fertility, 38(2), 123-128 (1993-03-01)
To find differences in effect on sperm motility of agents that increase intracellular cAMP: manganese ion, methyl-isobutyl-xanthine (MIX), 2-deoxyadenosine, glucose, and Mn-MIX and Mn-glucose. Nine men with asthenozoospermia vs. fertile donors. Sperm was washed in Hepes-buffered saline, motility tested by
Michela Giannecchini et al.
The international journal of biochemistry & cell biology, 37(4), 797-808 (2005-02-08)
In this paper, we report that cells undergoing metabolic stress conditions may use the ribose moiety of nucleosides as energy source to slow down cellular damage. In fact, the phosphorolytic cleavage of the N-glycosidic bond of nucleosides generates, without energy
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