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D1285

Sigma-Aldrich

2′,3′-Dideoxyadenosine

≥97% (HPLC)

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Synonym(s):
Dideoxyadenosine, ddA
Empirical Formula (Hill Notation):
C10H13N5O2
CAS Number:
4097-22-7
Molecular Weight:
235.24
Beilstein:
619924
EC Number:
223-853-2
MDL number:
MFCD00010534
UNSPSC Code:
41106305
PubChem Substance ID:
24893397
NACRES:
NA.51

Quality Level

200

Assay

≥97% (HPLC)

form

powder

optical activity

[α]/D -28.0±1.0

mp

181-184 °C (lit.)

solubility

water: 100 mg/mL, clear, colorless

storage temp.

2-8°C

SMILES string

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

InChI

1S/C10H13N5O2/c11-9-8-10(13-4-12-9)15(5-14-8)7-2-1-6(3-16)17-7/h4-7,16H,1-3H2,(H2,11,12,13)/t6-,7+/m0/s1

InChI key

WVXRAFOPTSTNLL-NKWVEPMBSA-N

Gene Information

human ... DCK(1633)

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General description

2′,3′-Dideoxyadenosine is a nucleoside analog of deoxyadenosine. On deamination, it is converted to dideoxyinosine. It inhibits adenylyl cyclase and may play a key role in the inhibition of tumor progression. It is a potent inhibitor of reverse transcriptase enzyme of human immunodeficiency virus.

Application

2′,3′-Dideoxyadenosine (ddA), a specific adenylyl cyclase inhibitor, is useful in biological process and pathway studies involving adenylyl cyclase activity and cAMP pool modulation.

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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James N Wilson et al.
Chembiochem : a European journal of chemical biology, 9(2), 279-285 (2007-12-12)
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Endocrinology, 150(1), 473-484 (2008-09-20)
Progestin stimulation of sperm hypermotility remains poorly understood despite having been described in numerous vertebrate species. We show here that progestin stimulation of sperm hypermotility in a teleost, the Atlantic croaker (Micropogonias undulatus) is associated with activation of an olfactory
Katharina Schönrath et al.
Molecular carcinogenesis, 50(5), 319-333 (2011-04-12)
VILIP-1 (visinin-like protein 1) is downregulated in various human squamous cell carcinoma (SCC). In a mouse skin SCC model VILIP-1 expression is reduced in aggressive tumor cells, accompanied by reduced cAMP levels. Overexpression of VILIP-1 in aggressive SCC cells led
Anabolism and mechanism of action of Ro24-5098, an isomer of 2',3'-dideoxyadenosine (ddA) with anti-HIV activity.
K B Frank et al.
Annals of the New York Academy of Sciences, 616, 408-414 (1990-01-01)
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