title: Synthesis and triplex forming properties of pyrimidine derivative containing extended functionality.
abstract: Two pyrimidine nucleosides have been synthesized containing extended hydrogen bonding functionality. In one case the side chain is based upon semicarbazide and in the second monoacetylated carbohydrazide was employed. DNA sequences could be prepared using both analogue nucleosides in a reverse coupling protocol, and provided that the normal capping step was eliminated and that the iodine-based oxidizing solution was replaced with one based upon 10-camphorsulfonyl oxaziridine. Both derivatives exhibited moderate effects in targeting selectively C-G base pairs embedded within a polypurine target sequence.
authors.affiliation: Department of Chemistry, Merkert Chemistry Center, Chestnut Hill, MA 02167, USA.
authors.forename: D A
authors.initials: DA
authors.lastname: Gianolio
authors.forename: L W
authors.initials: LW
authors.lastname: McLaughlin
mesh_terms: D020029:Base Pairing; D003841:Deoxycytidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D015195:Drug Design; D006834:Hydrazines / Q000737:chemistry; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D009690:Nucleic Acid Conformation; D009691:Nucleic Acid Denaturation; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis / Q000737:chemistry; D011743:Pyrimidines / Q000138:chemical synthesis / Q000737:chemistry*; D012663:Semicarbazides / Q000737:chemistry; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
chemical_list: D006834:Hydrazines; C400964:N(4)-(N(2)-acetamidoureido)-5'-O-4-4'-dimethoxytrityl-5-methyl-2'-deoxycytidine; C400963:N(4)-ureido-5'-O-4-4'-dimethoxytrityl-5-methyl-2'-deoxycytidine; D009838:Oligodeoxyribonucleotides; D011743:Pyrimidines; D012663:Semicarbazides; D003841:Deoxycytidine; C010059:carbamylhydrazine; C019289:carbohydrazide