title: Use of 1,2,4-dithiazolidine-3,5-dione (DtsNH) and 3-ethoxy-1,2,4-dithiazoline-5-one (EDITH) for synthesis of phosphorothioate-containing oligodeoxyribonucleotides.
abstract: Previous methods for the preparation of phosphorothioate-containing oligodeoxyribonucleotides rely on the reaction of phosphite triesters with sulfurizing reagents such as tetraethylthiuram disulfide (TETD) and 3H-1,2-benzodithiol-3-one 1,1-dioxide (Beaucage reagent). However, these and other sulfurizing reagents suffer from several disadvantages, and there is great impetus for the development of improved methods for sulfur transfer that are fully compatible with standard automated DNA synthesis. The present report describes the use of 1,2,4-dithiazolidine-3,5-dione (DtsNH) and 3-ethoxy-1,2,4-dithiazoline-5-one (EDITH) as effective sulfurizing reagents that meet these needs. Both reagents are easily prepared, and are stable upon prolonged room temperature storage in acetonitrile solution. The reagents are used at low concentrations (0.05 M) and for short reaction times (30 s). The methodology has been proven for the automated synthesis on 0.2-1.0 micromol scales of oligodeoxyribonucleotides, of length 6-20 bases, containing the phosphorothioate substitution at either a single site or at all positions.
authors.affiliation: Department of Chemistry, University of Minnesota, Minneapolis, 55455-0431, USA.
authors.forename: Q
authors.initials: Q
authors.lastname: Xu
authors.forename: K
authors.initials: K
authors.lastname: Musier-Forsyth
authors.forename: R P
authors.initials: RP
authors.lastname: Hammer
authors.forename: G
authors.initials: G
authors.lastname: Barany
mesh_terms: D001483:Base Sequence; D007202:Indicators and Reagents; D008956:Models, Chemical; D008969:Molecular Sequence Data; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis*; D013844:Thiazoles / Q000138:chemical synthesis; D045162:Thiazolidinediones; D013873:Thionucleotides / Q000138:chemical synthesis*
chemical_list: C099736:1,2,4-dithiazolidine-3,5-dione; C099735:3-ethoxy-1,2,4-dithiazoline-5-one; D007202:Indicators and Reagents; D009838:Oligodeoxyribonucleotides; D013844:Thiazoles; D045162:Thiazolidinediones; D013873:Thionucleotides