Synthesis and Separation of Dinucleoside Phenylphosphonate Diastereomers

@article{Hashmi1994SynthesisAS,
  title={Synthesis and Separation of Dinucleoside Phenylphosphonate Diastereomers},
  author={S. A. Nadeem Hashmi and Anil Kumar and S. B. Kacti},
  journal={Nucleosides, Nucleotides \& Nucleic Acids},
  year={1994},
  volume={13},
  pages={1039-1047}
}
Abstract Dinucleoside phenylphosphonates have been synthesized in excellent yields using 6-Nitrobenzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (NBOP) as a coupling reagent. A general method for the resolution of two diastereomers of phenylphosphonate dimers has been developed. 
4 Citations
SYNTHESIS AND CHARACTERIZATION OF PHOSPHATE-MODIFIED DNA-DIMERS WITH FLUORINE AS AN UNCHARGED LIGAND
Abstract The potential of the dinucleosidylphosphorofluoridates dCpFdG and dApFdT is described. Side products of the phosphoramidite coupling reaction are synthesized and characterized by
P-Chiral Oligonucleotides. Effect of Configuration at Phosphorus on Transport of Tetra(thymidine Methylphosphonate)s Across Organic Liquid Membrane
TLDR
The stereodependent transport of a P-stereoregular oligonucleotide through a model organic liquid membrane is described, extending the knowledge of the physicochemical properties of single-stranded methylphosphonate olig onucleotides in solution, and might facilitate cellular uptake of future antisense oligon nucleotide drugs.
Structure and Physical–Chemical Properties of Nitroazoles
The critical evaluation of a large body of the information on five-membered nitroazoles and nitrobenzazoles study by physical chemical methods – nuclear magnetic resonance (NMR), nuclear quadrupole

References

SHOWING 1-10 OF 14 REFERENCES
Synthesis and enzymatic properties of deoxyribooligonucleotides containing methyl and phenylphosphonate linkages.
TLDR
Both isomers of each dinucleotide analog are completely resistant to hydrolysis by spleen phosphodiesterase and acts as an inhibitor of the enzyme-catalyzed hydrolyzing of 5'-labeled oligothymidylic acid.
Nonionic nucleic acid analogues. Synthesis and characterization of dideoxyribonucleoside methylphosphonates.
TLDR
Since these nonionic oligonucleotide analogues are taken up by cells in culture, they show promise as molecular probes for the function and structure of nucleic acids inside living cells.
Methylphosphonates as probes of protein-nucleic acid interactions.
TLDR
When methylphosphonates were introduced into segment I, the affinity of lac repressor for the modified operators was shown to be dependent on the stereochemical configuration of the methylph phosphate.
Oligonucleoside Methylphosphonates as Antisense Reagents
  • P. Miller
  • Biology, Chemistry
    Bio/Technology
  • 1991
TLDR
Oligonucleoside methylphosphonate oligomers targeted against cellular or viral mRNA ini-tation codon or coding regions or against precursor mRNA splice sites effectively and specifically inhibit mRNA expression in cells.
Physicochemical properties of (R)- vs (S)-methylphosphonate substitution on antisense DNA hybridization determined by free energy perturbation and molecular dynamics
TLDR
State of the art advanced molecular computational methods and supercomputer technology were applied to identify key physicochemical determinants involved in stabilizing and destabilizing target hybridization.
B- to Z-DNA transition probed by oligonucleotides containing methylphosphonates.
TLDR
The studies suggest that the B--Z-DNA transition is regulated both thermodynamically and kinetically through hydrogen-bond interactions involving phosphate oxygens and the N-2 amino group of guanine.
Biochemical and biological effects of nonionic nucleic acid methylphosphonates.
TLDR
The failure of the oligodeoxyadenosine methylphosphonates to inhibit t RNALys (rabbit) amino-acylation suggests that there may be a difference between the structure of tRNALys or its interaction with aminoacyl synthetase in the Escherichia coli and rabbit systems.
...
...