Base-pairing systems related to TNA containing phosphoramidate linkages: synthesis of building blocks and pairing properties.
As part of a project that aims at screening TNA-related oligonucleotide systems in which threose backbone units may have some or all of their oxygen functions replaced by nitrogen, two TNA analogs containing (2'NH)- and (3'NH)-phosphoramidate groups, respectively, in place of phosphodiester groups were synthesized. They show base-pairing properties that are very similar to those of TNA itself. We also synthesized 2',3'-diamino analogs of alpha-L-threofuranosyl mononucleosides, yet attempts to convert them to TNA analogs containing phosphodiamidate linker groups were not successful. Such 2',3'-diamino derivatives of threofuranosyl nucleosides may be of interest, however, as building blocks of TNA analogs that contain non-phosphorous linker groups.
Ferencic
Mathias
M
The Skaggs Institute for Chemical Biology at The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA-92037, USA.
Reddy
Goverdhan
G
Wu
Xiaolin
X
Guntha
Sreenivasulu
S
Nandy
Jyoti
J
Krishnamurthy
Ramanarayanan
R
Eschenmoser
Albert
A
D000577:Amides / Q000138:chemical synthesis*; D020029:Base Pairing / Q000235:genetics; D003432:Cross-Linking Reagents / Q000138:chemical synthesis*; D009690:Nucleic Acid Conformation; D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000235:genetics; D010756:Phosphoric Acids / Q000138:chemical synthesis*; D013780:Tetroses / Q000138:chemical synthesis*
D000577:Amides; D003432:Cross-Linking Reagents; D009841:Oligonucleotides; D010756:Phosphoric Acids; D013780:Tetroses; C011067:phosphoramidic acid; C073321:erythrose