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D7400

Sigma-Aldrich

2′-Deoxyadenosine monohydrate

≥99%

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Synonym(s):
9-(2-Deoxy-β-D-ribofuranosyl)adenine, Adenine deoxyriboside
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:
41106305
PubChem Substance ID:
24894129
NACRES:
NA.51

biological source

synthetic (organic)

Quality Level

200

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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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.

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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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
Sonya M Schuh et al.
Biology of reproduction, 77(6), 960-969 (2007-09-01)
Activation of rapid motility apparently is one of the first steps of sperm capacitation and can be studied in vitro. Previously we found that 2-chloro-2'-deoxyadenosine or the catecholamine isoproterenol activates mouse sperm motility in vitro via a pathway mediated by
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
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
Nucleoside supplementation modulates mitochondrial DNA copy number in the dguok-/- zebrafish
Munro B, et al.
Human Molecular Genetics, 28(5), 796-803 (2018)
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