179017-27-7Relevant academic research and scientific papers
Stereochemical assignment and stereoselective synthesis of 3′-C-P-N-5′ Rp-ethyl phosphonamidate modified nucleic acid
Fairhurst,Collingwood,Lambert
, p. 473 - 476 (2007/10/03)
The configuration of the duplex stabilising 3′-C-P-N-5′ ethyl phosphonamidate nucleic acid backbone modification has been identified as Rp following the preparation of cyclic nucleoside analogues and NOE studies. Complimentary routes for formation of the key phosphonamidate nitrogen to phosphorus bond from stereochemically defined H-phosphinate intermediates, involving both a retention and inversion at the phosphorus centre, have been identified.
Synthesis and hybridisation properties of phosphonamidate ester modified nucleic acid
Fairhurst,Collingwood,Lambert,Taylor
, p. 467 - 472 (2007/10/03)
The replacement of the two backbone oxygen atoms of the phosphodiester linkage of DNA with carbon and nitrogen in the form of a phosphonamidate ester linkage, in both possible regioisomeric forms, is described. An alkylation reaction with the 3′-C-P-N-5′ methyl phosphonamidate regioisomer yielded the corresponding N-methylated analogues. For each example separation into individual phosphonamidate ester diastereoisomers was performed prior to incorporation into oligonucleotides. The effect upon duplex stability for DNA oligonucleotides containing each of these modifications with complimentary RNA is reported.
