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D1285

Sigma-Aldrich

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
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.

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Electrochemical oxidation of 2′, 3′-dideoxyadenosine at pyrolytic graphite electrode
Goyal RN, et al.
Electrochimica Acta, 53(16), 5354-5360 (2008)
Mark Kwaaitaal et al.
The Biochemical journal, 440(3), 355-365 (2011-08-19)
Binding of specific microbial epitopes [MAMPs (microbe-associated molecular patterns)] to PRRs (pattern recognition receptors) and subsequent receptor kinase activation are key steps in plant innate immunity. One of the earliest detectable events after MAMP perception is a rapid and transient
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
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)
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
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