D7400

2′-Deoxyadenosine monohydrate

Name: 2′-Deoxyadenosine monohydrate
Brand: SIGMA

≥99%, synthetic (organic), powder

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 CAS:

16373-93-6

Peso molecular:

269.26

NACRES:

NA.51

PubChem Substance ID:

24894129

UNSPSC Code:

41106305

EC Number:

213-488-7

MDL number:

MFCD00005754

Beilstein/REAXYS Number:

91015

Nombre del producto

2′-Deoxyadenosine monohydrate, ≥99%

InChI key

OLXZPDWKRNYJJZ-RRKCRQDMSA-N

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

SMILES string

[H]O[H].Nc1ncnc2n(cnc12)[C@H]3C[C@H](O)[C@@H](CO)O3

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

Quality Level

200

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Categorías relacionadas

Biochemicals

Nucleosides and Nucleotides

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.

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

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Certificados de análisis (COA)

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Regulation of glucose metabolism by adenine nucleotides in round spermatids from rat testes.

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

Provocation testing of human sperm motility using energy substrates and activators of the cyclic nucleotide system: II. Studies on sperm from asthenozoospermic subjects.

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

Uptake and utilization of nucleosides for energy repletion.

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

Adenosine and catecholamine agonists speed the flagellar beat of mammalian sperm by a non-receptor-mediated mechanism.

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

Variations in genomic DNA methylation during the long-term in vitro proliferation of oil palm embryogenic suspension cultures

Rival A, et al.

Plant Cell Reports, 32(3), 359-368 (2013)

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