A new selenium-transferring reagent—triphenylphosphine selenide

Bollmark, Martin; Stawiński, Jacek

doi:10.1039/b101002f

Cited by 41 publications

(15 citation statements)

References 13 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Solid-phase syntheses of PSeoligos were performed using a phosphoramidite or H-phosphonate approach with "selenation" of the P III intermediate [27,58,[84][85][86][87][88]. In all instances, the products consisted of a mixture of P-diastereoisomers.…”

Section: Phosphoroselenoatesmentioning

confidence: 99%

P-Chiral Oligonucleotides in Biological Recognition Processes

Guga

2007

CTMC

View full text Add to dashboard Cite

Internucleotide phosphodiester linkages in non-modified oligonucleotides are quickly degraded by nucleolytic enzymes present in the cells and this feature practically eliminates natural DNA and RNA molecules from medical applications and from many structural and mechanistic studies. P-chiral oligonucleotide analogs, in which one of the non-bridging phosphate oxygen atoms is substituted with another heteroatom (e.g. S, Se) or a chemical group (e.g. CH3, BH3(-)), have significantly greater nuclease resistance and also offer important possibilities for detailed studies of interactions with other biomolecules at the molecular level. Notably, these substitutions do not disrupt hydrogen bonding between nucleobases and affect the overall geometry of the oligomers to only low or moderate extent, although important changes of hydration patterns and changes of interactions with metal ions are observed. Such the probes, including isotopomeric species labeled with a heavy oxygen isotope, possessing phosphorus atoms of selected absolute configurations, have been used for elucidation of the mode of action of many enzymes (nucleases, transferases, kinases), ribozymes and DNA-zymes, as well as for investigations on thermodynamic stability of nucleic acids complexes (duplexes, triplexes, i-motif) and for studies on a mechanism of conformational changes of B-Z type. They are also useful tools for analysis of interactions of the phosphoryl oxygen atoms in natural precursors with functional groups of proteins. The synthetic routes to stereodefined forms of selected types of P-chiral oligonucleotides are presented, as well as recently developed methods for their configurational analysis at micromolar concentration. Selected examples of application of diastereomerically pure P-chiral oligonucleotides for structural, biochemical and biological experiments are discussed.

show abstract

Section: Phosphoroselenoatesmentioning

confidence: 99%

P-Chiral Oligonucleotides in Biological Recognition Processes

Guga

2007

CTMC

View full text Add to dashboard Cite

show abstract

“…Recently, we have proposed new selenium transferring reagents, namely tri phenylphosphine selenide [10] and tri phenyl phosphoroselenoate [11] for the introduction of selenium into nucleic acids. Regarding mechanistic aspects of the underlying reactions, two pathways for chalcogens transfer from P(V) to P(III) compounds were explored using density functional theory calculations (B3LYP, 6-31G*).…”

Section: Mechanism For the Chalcogens Exchange Reactionmentioning

confidence: 99%