✦ LIBER ✦

Solid phase synthesis of oligoribonucleotides using o-nitrobenzyl protection of 2'-hydroxyl via a phosphotriester approach

✍ Scribed by Toshiki Tanaka; Masaya Orita; Seiichi Uesugi; Morio Ikehara

Publisher: Elsevier Science
Year: 1988
Tongue: French
Weight: 510 KB
Volume: 44
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(01)86135-4

No coin nor oath required. For personal study only.

✦ Synopsis

Oligoribonucleotides with chain length of 6-9 were synthesized on a polystyrene support using o-nitrobenzyl protection of 2'-hydroxyls via phosphotiriester method.

The condensation reactions between N-acvl-5

and nucleoside bound to the resin using l-mesitylenesulfonyl-3-nitro-1H-1,2,4-triazole (MSNT) as a condensing agent were examined.-It was found that the condensation reaction usina MSNT was oromoted in the presence of 1-methylimidazoie as a cataiyst. A mixture of MSNT and 1-methylimidazole was also found to be effective in the condensation reaction involving a dinucleotide with 3'-phosphodiester.

The fully protected oligomer were deblocked and purified by chromatography in total yields of 3-21 % based on initial nucleoside bound to the support.

📜 SIMILAR VOLUMES

Use of 2-methylsulfonylethyl as a phosph

Use of 2-methylsulfonylethyl as a phosphorus protecting group in oligonucleotide synthesis via a phosphite triester approach

✍ C. Claesen; G.I. Tesser; C.E. Dreef; J.E. Marugg; G.A. van der Marel; J.H. van B 📂 Article 📅 1984 🏛 Elsevier Science 🌐 French ⚖ 204 KB

2-Methylsulfonylethoxy dichlorophosphine has been converted into the mono-N-morpholino derivative and applied for the preparation of 5'-D,N-protected d-nucleoside-3'-phosphoramidites. The latter intermediates could be used in the presence of 1-hydroxyben~otriazole for the formation of 3'-5'-phosphot

Use of the hexafluoro-2-butyl protecting

Use of the hexafluoro-2-butyl protecting group in the synthesis of DNA fragments via the phosphoramidite approach on solid supports

✍ Sung-Gug Kim; Kouichi Eida; Hiroshi Takaku 📂 Article 📅 1995 🏛 Elsevier Science 🌐 English ⚖ 210 KB

The hexafluoro-2-butyl (HFB) group is a new protecting group for internucleotidic bonds in the synthesis of oligodeoxydbonuclootides by the phosphoramidite approach. This group can be removed rapidly under the same condition as the 2--eyanoethyl group. Furthermore, we have found that the phosphityla

L-O-(2-malonyl)tyrosine (L-OMT) a new ph

L-O-(2-malonyl)tyrosine (L-OMT) a new phosphotyrosyl mimic suitably protected for solid-phase synthesis of signal transduction inhibitory peptides

✍ Bin Ye; Terrence R Burke Jr. 📂 Article 📅 1995 🏛 Elsevier Science 🌐 French ⚖ 216 KB

Preparation of a glycopeptide analogue o

Preparation of a glycopeptide analogue of type II collagen — Use of acid labile protective groups for carbohydrate moieties in solid phase synthesis of O-linked glycopeptides

✍ Johan Broddefalk; Karl-Erik Bergquist; Jan Kihlberg 📂 Article 📅 1996 🏛 Elsevier Science 🌐 French ⚖ 340 KB

Studies on stereospecific formation of P

Studies on stereospecific formation of P-chiral internucleotide linkage. Synthesis of (RP,RP)- and (SP,SP)-thymidylyl(3′,5′)thymidylyl(3′,5′)thymidine di(O,O-phosphorothioate) using 2-nitrobenzyl group as a new s-protection

✍ Z.J. Lesnikowski; M.M. Jaworska 📂 Article 📅 1989 🏛 Elsevier Science 🌐 French ⚖ 337 KB

RP,RP)-and (SP,SP)-diastereomers of thymidylyl(3',5')thymidyly1(3',5')thymidine di (O,O-phosphorothioate (6) were prepared in the stereospecific reaction of (RF)-or (SP)-isomer of 5'-0-monomethoxytritylthytnidine 3'U1~14-nitroph~nyl)-S-(X-nitrobenzyl)phosphorothioate] (2) with 5'-0tt activatd 3'Uace