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D1285

Sigma-Aldrich

2′,3′-Dideoxyadenosine

≥97% (HPLC)

Synonym(s):

Dideoxyadenosine, ddA

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5 MG
CLP 200,000
25 MG
CLP 695,000

CLP 200,000

Estimated to ship onApril 07, 2025

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5 MG
CLP 200,000
25 MG
CLP 695,000

About This Item

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

CLP 200,000

Estimated to ship onApril 07, 2025

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.[1] It is a potent inhibitor of reverse transcriptase enzyme of human immunodeficiency virus.[2]

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

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

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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
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
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
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
Electrochemical oxidation of 2′, 3′-dideoxyadenosine at pyrolytic graphite electrode
Goyal RN, et al.
Electrochimica Acta, 53(16), 5354-5360 (2008)
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