Synthesis of oligoribonucleotides by use of S,S-diphenyl n-monomethoxytrityl ribonucleoside 3'-phosphorodithioates
Identifieur interne : 004A15 ( Main/Exploration ); précédent : 004A14; suivant : 004A16Synthesis of oligoribonucleotides by use of S,S-diphenyl n-monomethoxytrityl ribonucleoside 3'-phosphorodithioates
Auteurs : Shinkichi Honda [Japon] ; Ken-Ichi Urakami [Japon] ; Kohji Koura [Japon] ; Kazunori Terada [Japon] ; Yoshinobu Sato [Japon] ; Kyoko Kohno [Japon] ; Mitsuo Sekine [Japon] ; Tsujiaki Hata [Japon]Source :
- Tetrahedron [ 0040-4020 ] ; 1984.
English descriptors
- Teeft :
- Acetal, Acetal proton, Acetate buffer, Alkaline hydrolysis, Ammonium acetate, Aqueous layer, Brome mosaic virus mrna, Chain length, Chem, Coevaporated, Complete removal, Considerable extent, Deprotection, Dmtr, Dmtr group, Elemental analysis, Equiv, Exchange chromatography, General procedure, Hata, High yields, Hydroxyl, Hydroxyl component, Ibid, Large amounts, Leader sequence, Major spot, Mesitylenedisulphonyl chloride, Methylene chloride, Mmol, Mmtr, Mmtr group, Mmtr groups, Molecular sieves, Nonamer, Nucleic acids, Oligomers, Oligoribonucleotides, Othp, Overall yields, Paper chromatography, Phenylthio, Phenylthio group, Phenylthio groups, Phosphinic acid, Potassium fluoride, Pyridine, Pyridinium form, Residual syrup, Ribonucleotide units, Room temp, Sekine, Selective removal, Several times, Silver acetate, Simultaneous deprotection, Soln, Symposium series, Tetrahedron, Tetrahedron letters, Tips group, Tokyo institute, Trifluoroacetic acid.
Abstract
Abstract: The fully protected ribonucleotide units (6a–d) have been synthesized in 42–62% overall yields by the 5- or 6-step reactions. The dimethoxtrityl, monomethoxytrityl, tetrahydropyran-2-yl, and phenylthio groups were introduced onto the 5'-OH, exo-amino, 2'-OH, and 3'-phosphoryl functions, respectively. The units were converted to the OH or phosphodiester components by treatment with trifluoroacetic acid or with phosphinic acid-triethylamine. Both the components were appropriately coupled by means of mesitylenedisulphonyl chloride 3-nitro-1,2,4-triazole to give dimers in high yields. This method was successfully applied to the synthesis of GpUpApUpUpApApUpAp, i.e. the 5'-terminal base sequence of brome mosaic virus m RNA No. 4 filament.
Url:
DOI: 10.1016/0040-4020(84)85114-5
Affiliations:
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227</wicri:noRegion></affiliation></author><author><name sortKey="Sato, Yoshinobu" sort="Sato, Yoshinobu" uniqKey="Sato Y" first="Yoshinobu" last="Sato">Yoshinobu Sato</name><affiliation wicri:level="1"><country xml:lang="fr">Japon</country><wicri:regionArea>Department of Life Chemistry, Tokyo Institute of Technology, Nagatsuta, Midoriku, Yokohama 227</wicri:regionArea><wicri:noRegion>Yokohama 227</wicri:noRegion></affiliation></author><author><name sortKey="Kohno, Kyoko" sort="Kohno, Kyoko" uniqKey="Kohno K" first="Kyoko" last="Kohno">Kyoko Kohno</name><affiliation wicri:level="1"><country xml:lang="fr">Japon</country><wicri:regionArea>Department of Life Chemistry, Tokyo Institute of Technology, Nagatsuta, Midoriku, Yokohama 227</wicri:regionArea><wicri:noRegion>Yokohama 227</wicri:noRegion></affiliation></author><author><name sortKey="Sekine, Mitsuo" sort="Sekine, Mitsuo" uniqKey="Sekine M" first="Mitsuo" last="Sekine">Mitsuo Sekine</name><affiliation wicri:level="1"><country xml:lang="fr">Japon</country><wicri:regionArea>Department of Life Chemistry, Tokyo Institute of Technology, Nagatsuta, Midoriku, Yokohama 227</wicri:regionArea><wicri:noRegion>Yokohama 227</wicri:noRegion></affiliation></author><author><name sortKey="Hata, Tsujiaki" sort="Hata, Tsujiaki" uniqKey="Hata T" first="Tsujiaki" last="Hata">Tsujiaki Hata</name><affiliation wicri:level="1"><country xml:lang="fr">Japon</country><wicri:regionArea>Department of Life Chemistry, Tokyo Institute of Technology, Nagatsuta, Midoriku, Yokohama 227</wicri:regionArea><wicri:noRegion>Yokohama 227</wicri:noRegion></affiliation></author></analytic><monogr></monogr><series><title level="j">Tetrahedron</title><title level="j" type="abbrev">TET</title><idno type="ISSN">0040-4020</idno><imprint><publisher>ELSEVIER</publisher><date type="published" when="1984">1984</date><biblScope unit="volume">40</biblScope><biblScope unit="issue">1</biblScope><biblScope unit="page" from="153">153</biblScope><biblScope unit="page" to="163">163</biblScope></imprint><idno type="ISSN">0040-4020</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">0040-4020</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="Teeft" xml:lang="en"><term>Acetal</term><term>Acetal proton</term><term>Acetate buffer</term><term>Alkaline hydrolysis</term><term>Ammonium acetate</term><term>Aqueous layer</term><term>Brome mosaic virus mrna</term><term>Chain length</term><term>Chem</term><term>Coevaporated</term><term>Complete removal</term><term>Considerable extent</term><term>Deprotection</term><term>Dmtr</term><term>Dmtr group</term><term>Elemental analysis</term><term>Equiv</term><term>Exchange chromatography</term><term>General procedure</term><term>Hata</term><term>High yields</term><term>Hydroxyl</term><term>Hydroxyl component</term><term>Ibid</term><term>Large amounts</term><term>Leader sequence</term><term>Major spot</term><term>Mesitylenedisulphonyl chloride</term><term>Methylene chloride</term><term>Mmol</term><term>Mmtr</term><term>Mmtr group</term><term>Mmtr groups</term><term>Molecular sieves</term><term>Nonamer</term><term>Nucleic acids</term><term>Oligomers</term><term>Oligoribonucleotides</term><term>Othp</term><term>Overall yields</term><term>Paper chromatography</term><term>Phenylthio</term><term>Phenylthio group</term><term>Phenylthio groups</term><term>Phosphinic acid</term><term>Potassium fluoride</term><term>Pyridine</term><term>Pyridinium form</term><term>Residual syrup</term><term>Ribonucleotide units</term><term>Room temp</term><term>Sekine</term><term>Selective removal</term><term>Several times</term><term>Silver acetate</term><term>Simultaneous deprotection</term><term>Soln</term><term>Symposium series</term><term>Tetrahedron</term><term>Tetrahedron letters</term><term>Tips group</term><term>Tokyo institute</term><term>Trifluoroacetic acid</term></keywords></textClass><langUsage><language ident="en">en</language></langUsage></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Abstract: The fully protected ribonucleotide units (6a–d) have been synthesized in 42–62% overall yields by the 5- or 6-step reactions. The dimethoxtrityl, monomethoxytrityl, tetrahydropyran-2-yl, and phenylthio groups were introduced onto the 5'-OH, exo-amino, 2'-OH, and 3'-phosphoryl functions, respectively. The units were converted to the OH or phosphodiester components by treatment with trifluoroacetic acid or with phosphinic acid-triethylamine. Both the components were appropriately coupled by means of mesitylenedisulphonyl chloride 3-nitro-1,2,4-triazole to give dimers in high yields. This method was successfully applied to the synthesis of GpUpApUpUpApApUpAp, i.e. the 5'-terminal base sequence of brome mosaic virus m RNA No. 4 filament.</div></front></TEI><affiliations><list><country><li>Japon</li></country></list><tree><country name="Japon"><noRegion><name sortKey="Honda, Shinkichi" sort="Honda, Shinkichi" uniqKey="Honda S" first="Shinkichi" last="Honda">Shinkichi Honda</name></noRegion><name sortKey="Hata, Tsujiaki" sort="Hata, Tsujiaki" uniqKey="Hata T" first="Tsujiaki" last="Hata">Tsujiaki Hata</name><name sortKey="Kohno, Kyoko" sort="Kohno, Kyoko" uniqKey="Kohno K" first="Kyoko" last="Kohno">Kyoko Kohno</name><name sortKey="Koura, Kohji" sort="Koura, Kohji" uniqKey="Koura K" first="Kohji" last="Koura">Kohji Koura</name><name sortKey="Sato, Yoshinobu" sort="Sato, Yoshinobu" uniqKey="Sato Y" first="Yoshinobu" last="Sato">Yoshinobu Sato</name><name sortKey="Sekine, Mitsuo" sort="Sekine, Mitsuo" uniqKey="Sekine M" first="Mitsuo" last="Sekine">Mitsuo Sekine</name><name sortKey="Terada, Kazunori" sort="Terada, Kazunori" uniqKey="Terada K" first="Kazunori" last="Terada">Kazunori Terada</name><name sortKey="Urakami, Ken Ichi" sort="Urakami, Ken Ichi" uniqKey="Urakami K" first="Ken-Ichi" last="Urakami">Ken-Ichi Urakami</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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