Literature DB >> 16737305

Facile photocyclization chemistry of 5-phenylthio-2'-deoxyuridine in duplex DNA.

Yu Zeng1, Huachuan Cao, Yinsheng Wang.   

Abstract

We report here the synthesis of 5-phenylthio-2'-deoxyuridine (d(PhS)U), its incorporation into oligodeoxynucleotides (ODNs), and its photocyclization chemistry. Irradiation of dinucleoside monophosphate d((PhS)UG) and d(PhS)U-bearing duplex ODNs with 254 nm light results in the facile formation of a cyclic product where the C6 of uracil is covalently bonded to the C2 of the phenyl ring. The chemistry reported here may serve as the basis for the efficient preparation of a new class of duplex DNA with an extended pi system. [reaction: see text]

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Year:  2006        PMID： 16737305      PMCID： PMC2532586          DOI： 10.1021/ol060659v

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  19 in total

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