60129-59-1
Chemical Structure
7-Deaza-2'-deoxyadenosine
- CAS No.: 60129-59-1
- Formula:C11H14N4O3
- Molecular Weight:250.26
IUPAC Name: (2R,3S,5R)-5-(4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol
InChIKey: NIJSNUNKSPLDTO-DJLDLDEBSA-N
SMILES: NC1=C2C(N([C@@H]3O[C@@H]([C@H](C3)O)CO)C=C2)=NC=N1
Biological Activity: 7-Deaza-2'-deoxyadenosine is an isosteric dATP analog of 2'-deoxyadenosine. 7-Deaza-2'-deoxyadenosine is recognized by various DNA polymerases and incorporated into DNA strands as a substrate. 7-Deaza-2'-deoxyadenosine undergoes a bioorthogonal inverse electron demand Diels-Alder reaction with tetrazine-modified molecules, enabling site-specific labeling of DNA, surface antibody immobilization and intracellular fluorescent labeling. 7-Deaza-2'-deoxyadenosine reduces the DNA curvature of d(A6)·d(T6) fragments and the stability of DNA/RNA double helices, and leads to decreased antisense activity against SV40 T Antigen. 7-Deaza-2'-deoxyadenosine finds application in the research field of SV40 T Antigen-related cancers[1][2][3][4].
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7-Deaza-2'-deoxyadenosine | 99.90% | 7-Deaza-2'-deoxyadenosine is an isosteric dATP analog of 2'-deoxyadenosine. 7-Deaza-2'-deoxyadenosine is recognized by various DNA polymerases and incorporated into DNA strands as a substrate. 7-Deaza-2'-deoxyadenosine undergoes a bioorthogonal inverse electron demand Diels-Alder reaction with tetrazine-modified molecules, enabling site-specific labeling of DNA, surface antibody immobilization and intracellular fluorescent labeling. 7-Deaza-2'-deoxyadenosine reduces the DNA curvature of d(A6)·d(T6) fragments and the stability of DNA/RNA double helices, and leads to decreased antisense activity against SV40 T Antigen. 7-Deaza-2'-deoxyadenosine finds application in the research field of SV40 T Antigen-related cancers. | ||||||||||||||||||||
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References
- [1]. Ploschik D, et al. DNA Primer Extension with Cyclopropenylated 7-Deaza-2'-deoxyadenosine and Efficient Bioorthogonal Labeling in Vitro and in Living Cells. Chembiochem. 2018;19(18):1949-1953. [Content Brief]
- [2]. Seela F, et al. 7-Deaza-2′-deoxyadenosine and 3-deaza-2′-deoxyadenosine replacing dA within d (A6)-tracts: differential bending at 3′-and 5′-junctions of d (A6) d (T6) and B-DNA[J]. Nucleic acids research, 1992, 20(9): 2297-2306.
- [3]. Buhr CA, et al. Oligodeoxynucleotides containing C-7 propyne analogs of 7-deaza-2'-deoxyguanosine and 7-deaza-2'-deoxyadenosine. Nucleic Acids Res. 1996;24(15):2974-2980. [Content Brief]
- [4]. Reisacher U, et al. Triazine-Modified 7-Deaza-2'-deoxyadenosines: Better Suited for Bioorthogonal Labeling of DNA by PCR than 2'-Deoxyuridines. Bioconjug Chem. 2019;30(6):1773-1780. [Content Brief]
