title: Synthesis of activated 3'-amino-3'-deoxy-2-thio-thymidine, a superior substrate for the nonenzymatic copying of nucleic acid templates.
abstract: We present a scalable synthesis of 3'-amino-3'-deoxy-2-thio-thymidine-5'-phosphoro-2-methylimidazolide, an activated monomer that can copy adenosine residues in nucleic acid templates rapidly without a polymerase. The sulfur atom substitution enhances the rate of template copying by 5-fold compared with the 3'-amino-3'-deoxy-T monomer, while the 3'-amino monomers exhibit a 2- to 30-fold enhancement compared with their ribonucleotide counterparts.
authors: Howard Hughes Medical Institute, Department of Molecular Biology and Center for Computational and Integrative Biology, Massachusetts General Hospital, 185 Cambridge Street, Boston, Massachusetts 02114, USA. szostak@molbio.mgh.harvard.edu and Department of Genetics, Harvard Medical School, 77 Avenue Louis Pasteur, Boston, Massachusetts 02115, USA.
authors: Enver Cagri
authors: EC
authors: Izgu
authors: Howard Hughes Medical Institute, Department of Molecular Biology and Center for Computational and Integrative Biology, Massachusetts General Hospital, 185 Cambridge Street, Boston, Massachusetts 02114, USA. szostak@molbio.mgh.harvard.edu and Department of Genetics, Harvard Medical School, 77 Avenue Louis Pasteur, Boston, Massachusetts 02115, USA.
authors: Seung Soo
authors: SS
authors: Oh
authors: Howard Hughes Medical Institute, Department of Molecular Biology and Center for Computational and Integrative Biology, Massachusetts General Hospital, 185 Cambridge Street, Boston, Massachusetts 02114, USA. szostak@molbio.mgh.harvard.edu and Department of Genetics, Harvard Medical School, 77 Avenue Louis Pasteur, Boston, Massachusetts 02115, USA and Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford St., Cambridge, Massachusetts 02138, USA.
authors: Jack W
authors: JW
authors: Szostak
mesh_terms: D015224:Dideoxynucleosides / Q000737:chemistry*; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009696:Nucleic Acids / Q000737:chemistry*; D012265:Ribonucleotides / Q000737:chemistry*; D013455:Sulfur / Q000737:chemistry*; D013936:Thymidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: C000609930:3'-amino-3'-deoxy-2-thio-thymidine; C000609931:3'-amino-3'-deoxy-2-thio-thymidine-5'-phosphoro-2-methylimidazolide; D015224:Dideoxynucleosides; D007093:Imidazoles; D009696:Nucleic Acids; D012265:Ribonucleotides; C019252:3'-aminothymidine; D013455:Sulfur; D013936:Thymidine