title: Labeling of DNA via rearrangement of S-2-aminoethyl phosphorothioates to N-(2-mercaptoethyl)phosphoramidates.
abstract: 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.
authors.affiliation: Centre for DNA Nanotechnology at iNANO and Department of Chemistry, University of Aarhus, Langelandsgade 140, DK-8000 Arhus C, Denmark.
authors.forename: Menglin
authors.initials: M
authors.lastname: Chen
authors.forename: Kurt V
authors.initials: KV
authors.lastname: Gothelf
mesh_terms: D000577:Amides / Q000737:chemistry*; D001665:Binding Sites; D004247:DNA / Q000737:chemistry*; D015394:Molecular Structure; D009946:Organothiophosphorus Compounds / Q000737:chemistry*; D000644:Quaternary Ammonium Compounds / Q000737:chemistry; D013194:Staining and Labeling
chemical_list: C528772:2-bromoethylammonium bromide; D000577:Amides; D009946:Organothiophosphorus Compounds; D000644:Quaternary Ammonium Compounds; D004247:DNA