Reinvestigation of deoxyribonucleoside phosphorothioites: synthesis and properties of deoxyribonudeoside-3′ dimethyl phosphites

Nagai, Hisashi; Fujiwara, Toshiki; Fujii, Mitsuo; Fujii, Sekine; Hata, Tsujiaki

doi:10.1093/nar/17.21.8581

Cited by 14 publications

(2 citation statements)

References 2 publications

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A molecular sieves, no stabilizer) Diisopropylethylamine (DIPEA, anhydrous, dried over CaH 2 , distilled from CaH 2 ) 2-Cyanoethoxy-(N, N-diisopropylamino)chlorophosphine (synthesized as described in Nagai et al, 1989;Tanimura et al, 1989) 200-mL round-bottom flasks with argon-filled balloon Rotary evaporator and vacuum pump

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“….15.3. Materials 2 -Deoxyguanosine (S.1c; Yamasa Shoyu) Pyridine (anhydrous, dried over 4-• A molecular sieves, distilled from CaH 2 ) Methanol (MeOH; Wako, anhydrous, dried over 4-• A molecular sieves) Argon source N,N-Dimethylformamide dimethyl acetal (Tokyo Kasei Co. Ltd.; http://www.tokyokasei.co.jp/) 4,4 -Dimethoxytrityl chloride (DMTr-Cl) Chloroform (CHCl 3 ) Brine (saturated aqueous NaCl) Sodium sulfate (Na 2 SO 4 , anhydrous) Diisopropyl ether Ammonium hydroxide Silica gel (Wakogel C-200, 75 to 150 µm) Hexane Toluene (anhydrous, dried over 4-• A molecular sieves) Dichloromethane (CH 2 Cl 2 , anhydrous, dried over 4-• A molecular sieves) Diisopropylethylamine (DIPEA, anhydrous, dried over CaH 2 , distilled from CaH 2 ) 2-Cyanoethoxy-(N,N-diisopropylamino)chlorophosphine (synthesized as describedinNagai et al, 1989;Tanimura et al, 1989) Triethylamine (Wako, distilled from CaH 2 ) 100-and 200-mL round-bottom flasks with argon-filled balloon Rotary evaporator and vacuum pump Thin-layer chromatography (TLC) silica plates (Kieselgel 60 F 254 ; 0.2 mm thick;…”

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DNA Synthesis Without Base Protection Using the Phosphoramidite Approach

Ohkubo

Seio

Sekine

2006

CP Nucleic Acid Chemistry

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In the strategy of DNA synthesis without base protection, a recent O-selective phosphorylation procedure known as the "activated phosphite method" is used to generate reactive phosphite intermediates from N-unprotected phosphoramidite building blocks. This new strategy proved to be advantageous over previous strategies because the cleavage of the N-P(III) bond, which can be formed by the significant phosphitylation of the nucleobase amino groups, can be omitted. The activated phosphite method provides an attractive route to high-throughput synthesis of DNA and the synthesis of alkali-labile modified DNAs such as oligonucleotides containing DNA lesions. This unit presents two convenient methods for the synthesis of N-unprotected deoxynucleoside 3'-phosphoramidite units and detailed procedures for automated synthesis of oligodeoxyribonucleotides from these phosphoramidite units.

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DNA Synthesis Without Base Protection Using the Phosphoramidite Approach

Ohkubo

Seio

Sekine

2006

CP Nucleic Acid Chemistry

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Base‐Pairing Systems Related to TNA Containing Phosphoramidate Linkages: Synthesis of Building Blocks and Pairing Properties

Ferencic

Reddy

et al. 2004

Chemistry & Biodiversity

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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.

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