PAPER: Labeling of DNA via rearrangement of s-2-aminoethyl phosphorothioates to n-(2-mercaptoethyl)phosphoramidates

Chen, M.; Gothelf, K. V.

Org. Biomol. Chem. 2008, 6, 908–911, doi: 10.1039/b717664c

Centre for DNA Nanotechnology at iNANO and Department of Chemistry, University of Aarhus, Langelandsgade 140, DK-8000 Arhus C, Denmark


The reaction of phosphorothioates in DNA with 2-bromoethylammonium bromide results in S-2-aminoethyl phosphorothioates, which can rearrange to N-(2-mercaptoethyl)phosphoramidates providing a facile method for the generation of site-specific thiol labeling of DNA sequences. The applicability of this method was demonstrated by conjugation of the thiolated DNA sequence with Na-(3-maleimidylpropionyl) biocytin and Alexa Fluor 546 C5-maleimide.

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