Details

Autor(en) / Beteiligte

• Gjonaj, Lorina
• Roelfes, Gerard

Titel

Selective chemical modification of DNA with alkoxy- and benzyloxyaminesElectronic supplementary information (ESI) available. See DOI: 10.1039/c5ob00595g

Erscheinungsjahr

2015-05

Link zum Volltext

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• A new method for the selective chemical modification of DNA at cytosine nucleobases using alkoxy- and benzyloxyamines is presented. It is shown that in particular benzyloxyamines are effective DNA modifying agents, giving rise to almost exclusive formation of the mono addition products. By using a bifunctional derivative, that is, p -azidobenzyloxyamine hydrochloride, an azide moiety, which is a convenient handle for further functionalization, could be introduced into the DNA. The azido modified DNA was then further reacted in a copper( i )-monophos catalysed 1,3-dipolar cycloaddition. These results illustrate the potential of the presented method for application in site and chemo-selective modification of DNA. DNA is modified selectively at cytosine with benzyloxyamine and -derivatives carrying handles for click reactions.