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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:
Molecular Weight:
269.26
Beilstein:
91015
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.51

biological source

synthetic (organic)

Quality Level

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.

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

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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
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
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
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)

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