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Merck
CN

D1285

2′,3′-Dideoxyadenosine

≥97% (HPLC)

Synonym(s):

Dideoxyadenosine, ddA

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About This Item

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

Key Documents

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Product Name

2′,3′-Dideoxyadenosine, ≥97% (HPLC)

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

SMILES string

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

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

Quality Level

200

Gene Information

human ... DCK(1633)

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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.

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.

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
1364104V
1364104
426060/1
067K2651
096K2503

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Pharmacokinetics of 2′, 3′-dideoxyadenosine and 2′, 3′-dideoxyinosine in patients with severe human immunodeficiency virus infection
Hartman NR, et al.
Clinical Pharmacology and Therapeutics, 47(5), 647-654 (1990)
Christopher Tubbs et al.
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
Elena Grossini et al.
Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology, 23(1-3), 87-96 (2009-03-04)
Urocortin II has previously been shown in anesthetized pigs to increase coronary blood flow through activation of the endothelial nitric oxide synthase (eNOS) pathway and involvement of the subtype 2 of corticotropin releasing factor receptors (CRFR2). However, little information has
James N Wilson et al.
Chembiochem : a European journal of chemical biology, 9(2), 279-285 (2007-12-12)
Fluorescent nucleosides are widely used as probes of biomolecular structure and mechanism in the context of DNA, but they often exhibit low quantum yields because of quenching by neighboring DNA bases. Here we characterize the quenching by DNA of fluorescent
Xiaohong Liu et al.
Nucleic acids research, 35(21), 7140-7149 (2007-10-19)
Telomerase adds telomeric DNA repeats to the ends of linear chromosomal DNA. 3'-Azido-3'-deoxythymidine 5'-triphosphate (AZTTP) is a known telomerase inhibitor. To obtain more selective and potent inhibitors that can be employed as tools for studying telomerase, we investigated the telomerase-inhibitory
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