oxathiaphospholane and phosphorodithioic-acid

oxathiaphospholane has been researched along with phosphorodithioic-acid* in 2 studies

Reviews

1 review(s) available for oxathiaphospholane and phosphorodithioic-acid

Article	Year
Synthesis of phosphorothioate oligonucleotides with stereodefined phosphorothioate linkages. Current protocols in nucleic acid chemistry, 2003, Volume: Chapter 4 A method for solid-phase synthesis of stereodefined PS-oligos via an oxathiaphospholane approach using pure P-diastereomers of nucleoside oxathiaphospholane monomers is described. The oxathiaphospholane monomers are synthesized by phosphitylation of 5'-O-DMTr-N-protected deoxyribonucleosides with 2-chloro-spiro-4,4-pentamethylene-1,3,2-oxathiaphospholane followed by sulfurization. The procedure is general and may be applied to other analogs, depending on the aldehyde (or mercaptoalcohol) used. Starting from an 18O-labeled mercaptoalcohol, the corresponding 18O-labeled phosphitylating reagent and nucleoside monomers can be obtained and used for synthesis of labeled stereodefined PS-oligos, which are useful for studying mechanisms of enzymatic reactions. Details are provided for chromatographic separation of the 5'-O-DMTr-N-protected-deoxyribonucleoside-3'-O-(2-thio-spiro-4,4-pentamethylene-1,3,2-oxathiaphospholane)s into their P-diastereomers, and for manual solid-phase synthesis of PS-oligos. Oxidation of 5'-O-DMTr-N-protected-deoxyribonucleoside-3'-O-(2-thio-spiro-4,4-pentamethylene-1,3,2-oxathiaphospholane)s with selenium dioxide yields their 2-oxo-analogs, which are suitable either for elongation of stereodefined PS-oligos with segments consisting of unmodified nucleotide units possessing phosphate internucleotide linkages, or for generating isotopomeric 18O-labeled PO-oligos of predetermined P-chirality. Topics: Chemistry, Organic; Cyclohexanecarboxylic Acids; Cyclohexanes; Disulfides; Models, Biological; Nucleic Acid Conformation; Nucleotides; Organothiophosphorus Compounds; Phosphates; Phosphorothioate Oligonucleotides; Ribose; Sarcosine; Solvents; Stereoisomerism; Succinic Acid	2003

Article

Year

Synthesis of phosphorothioate oligonucleotides with stereodefined phosphorothioate linkages.

Current protocols in nucleic acid chemistry, 2003, Volume: Chapter 4

A method for solid-phase synthesis of stereodefined PS-oligos via an oxathiaphospholane approach using pure P-diastereomers of nucleoside oxathiaphospholane monomers is described. The oxathiaphospholane monomers are synthesized by phosphitylation of 5'-O-DMTr-N-protected deoxyribonucleosides with 2-chloro-spiro-4,4-pentamethylene-1,3,2-oxathiaphospholane followed by sulfurization. The procedure is general and may be applied to other analogs, depending on the aldehyde (or mercaptoalcohol) used. Starting from an 18O-labeled mercaptoalcohol, the corresponding 18O-labeled phosphitylating reagent and nucleoside monomers can be obtained and used for synthesis of labeled stereodefined PS-oligos, which are useful for studying mechanisms of enzymatic reactions. Details are provided for chromatographic separation of the 5'-O-DMTr-N-protected-deoxyribonucleoside-3'-O-(2-thio-spiro-4,4-pentamethylene-1,3,2-oxathiaphospholane)s into their P-diastereomers, and for manual solid-phase synthesis of PS-oligos. Oxidation of 5'-O-DMTr-N-protected-deoxyribonucleoside-3'-O-(2-thio-spiro-4,4-pentamethylene-1,3,2-oxathiaphospholane)s with selenium dioxide yields their 2-oxo-analogs, which are suitable either for elongation of stereodefined PS-oligos with segments consisting of unmodified nucleotide units possessing phosphate internucleotide linkages, or for generating isotopomeric 18O-labeled PO-oligos of predetermined P-chirality.

Topics: Chemistry, Organic; Cyclohexanecarboxylic Acids; Cyclohexanes; Disulfides; Models, Biological; Nucleic Acid Conformation; Nucleotides; Organothiophosphorus Compounds; Phosphates; Phosphorothioate Oligonucleotides; Ribose; Sarcosine; Solvents; Stereoisomerism; Succinic Acid

2003

Other Studies

1 other study(ies) available for oxathiaphospholane and phosphorodithioic-acid

Article	Year
Stereocontrolled synthesis of LNA dinucleoside phosphorothioate by the oxathiaphospholane approach. Bioorganic & medicinal chemistry letters, 2001, Apr-23, Volume: 11, Issue:8 The application of the oxathiaphospholane approach for the stereocontrolled synthesis of LNA dinucleoside phosphorothioate is described. The reaction of ring opening condensation proceeds in CH3CN solution in high yield and with over 96% stereoselectivity. One of diastereomers of LNA dinucleoside phosphorothioate (presumably R(P)) was found to be readily digested by svPDE. Topics: Chromatography, High Pressure Liquid; Magnetic Resonance Spectroscopy; Nucleic Acid Conformation; Nucleotides; Oligonucleotides; Phosphates; Phosphodiesterase I; Phosphoric Diester Hydrolases; Ribose; Stereoisomerism	2001

Article

Year

Stereocontrolled synthesis of LNA dinucleoside phosphorothioate by the oxathiaphospholane approach.

Bioorganic & medicinal chemistry letters, 2001, Apr-23, Volume: 11, Issue:8

The application of the oxathiaphospholane approach for the stereocontrolled synthesis of LNA dinucleoside phosphorothioate is described. The reaction of ring opening condensation proceeds in CH3CN solution in high yield and with over 96% stereoselectivity. One of diastereomers of LNA dinucleoside phosphorothioate (presumably R(P)) was found to be readily digested by svPDE.

Topics: Chromatography, High Pressure Liquid; Magnetic Resonance Spectroscopy; Nucleic Acid Conformation; Nucleotides; Oligonucleotides; Phosphates; Phosphodiesterase I; Phosphoric Diester Hydrolases; Ribose; Stereoisomerism

2001