title: N2'-->p3' phosphoramidate glycerol nucleic acid as a potential alternative genetic system.
abstract: Glycerol nucleic acid (GNA) is an interesting base-pairing system with an acyclic, three-carbon backbone. In the present study, GNA analogues with N2'-->P3' phosphoramidate linkages (npGNA) have been synthesized and their base-pairing properties examined. Thermal denaturation and circular dichroism studies show that npGNA can form stable duplexes with itself and with GNA. Furthermore, we show that npGNA can be assembled by template-directed ligation of 3'-imidazole-activated-2'-amino GNA dinucleotides. These results suggest that npGNA is a potential candidate for a self-replicating system based upon phosphoramidate linkages.
authors.affiliation: Howard Hughes Medical Institute, and Department of Molecular Biology and Center for Computational and Integrative Biology, Massachusetts General Hospital, 185 Cambridge Street, Boston, Massachusetts 02114, USA.
authors.forename: Jesse J
authors.initials: JJ
authors.lastname: Chen
authors.forename: Xin
authors.initials: X
authors.lastname: Cai
authors.forename: Jack W
authors.initials: JW
authors.lastname: Szostak
mesh_terms: D000577:Amides / Q000737:chemistry*; D040761:Biomimetic Materials / Q000737:chemistry; D002942:Circular Dichroism; D004247:DNA / Q000737:chemistry / Q000235:genetics; D040342:Genetic Structures; D005990:Glycerol / Q000031:analogs & derivatives*; D007093:Imidazoles / Q000737:chemistry; D009696:Nucleic Acids / Q000737:chemistry* / Q000235:genetics; D009711:Nucleotides / Q000737:chemistry / Q000235:genetics; D010756:Phosphoric Acids / Q000737:chemistry*; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
chemical_list: D000577:Amides; D007093:Imidazoles; D009696:Nucleic Acids; D009711:Nucleotides; D010756:Phosphoric Acids; D004247:DNA; C011067:phosphoramidic acid; D005990:Glycerol