Synthesis of 2-azido-1,N6-etheno and 2-azido analogs of deoxyadenosine as nucleotide photoaffinity probes

Article abstract of DOI:10.1080/15257779508014653

We prepared 2-azido-1,N⁶-etheno-2'-deoxyadenosine 5'-monophosphate (7b) by activation of the 2-thio analog 4b by two methods. In the preferred method, 4b was treated with 2,4-dinitrofluorobenzene in 50% aqueous acetonitrile, and the resultant thioether was cleaved with hydrazoic acid, yielding the 2-azido-1,N⁶-etheno analog 7b in 70% isolated yield. N-bromoacetamide oxidized the etheno group of 7b, giving the 2-azido analog of dAMP 9b in 78% yield.

Full text of DOI:10.1080/15257779508014653

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Synthesis of 2-Azido-1,N6-Etheno and
2-Azido Analogs of Deoxyadenosine as
Nucleotide Photoaffinity Probes
Diane Flaherty a , Preeti Balse a , Ke Li a , Bob M. Moore a
Michael B. Doughty a
&
a Department of Medicinal Chemistry , University of Kansas ,
Lawrence, KS, 66045
Published online: 24 Sep 2006.
To cite this article: Diane Flaherty , Preeti Balse , Ke Li , Bob M. Moore & Michael B.
Doughty (1995) Synthesis of 2-Azido-1,N6-Etheno and 2-Azido Analogs of Deoxyadenosine
as Nucleotide Photoaffinity Probes, Nucleosides and Nucleotides, 14:1-2, 65-76, DOI:
10.1080/15257779508014653
To link to this article: http://dx.doi.org/10.1080/15257779508014653
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