title: Selective chemical modification of DNA with alkoxy- and benzyloxyamines.
abstract: 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.
authors.affiliation: Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands. j.g.roelfes@rug.nl.
authors.forename: Lorina
authors.initials: L
authors.lastname: Gjonaj
authors.forename: Gerard
authors.initials: G
authors.lastname: Roelfes
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D003300:Copper / Q000737:chemistry; D061565:Cycloaddition Reaction; D003596:Cytosine / Q000737:chemistry; D004247:DNA / Q000737:chemistry*; D006898:Hydroxylamines / Q000737:chemistry*
chemical_list: D000438:Alcohols; D001386:Azides; D006898:Hydroxylamines; C059688:alkoxyl radical; C017064:benzyloxyamine; D003300:Copper; D003596:Cytosine; D004247:DNA