Stereocontrolled Synthesis of Oligo(nucleoside phosphorothioate)s
Identifieur interne : 001434 ( Istex/Corpus ); précédent : 001433; suivant : 001435Stereocontrolled Synthesis of Oligo(nucleoside phosphorothioate)s
Auteurs : Wojciech J. Stec ; Andrzej WilkSource :
- Angewandte Chemie International Edition in English [ 0570-0833 ] ; 1994-04-18.
Abstract
Encouraging results obtained for modulation of gene expression by antisense oligonucleotides and their analogues have kindled hopes for a new generation of therapeutics against viral infections, cancer, and many other diseases. Among such analogues, oligo(nucleoside phosphorothioate)s (Oligo‐S) have generally shown the highest efficacy in inhibiting the biosynthesis of “unwanted” proteins. The first clinical trials of antisense agents are now in progress using Oligo‐S against genital warts and acute myeloid leukemia, and tests of Oligo‐S against AIDS should follow soon. Nevertheless, their mechanism of action, internalization, cellular trafficking, subcellular localization, and interaction with cellular proteins is still poorly understood. It is assumed a priori that application involves rapid and efficient molecular recognition of target RNA by Oligo‐S; however, the effects of the chirality of Oligo‐S have so far been unappreciated, because Oligo‐S has not yet been synthesized with stereocontrol. Indeed, the diastereomeric composition of Oligo‐S has never been determined, primarily because of the lack of appropriate analytical methods. Since each of the diastereomers is a stereochemically unique chemical entity, questions arise as to which diastereomer is responsible for an observed biological response, including positive (curative) or possibly negative (toxic) side effects. In this review we intend provide a perhaps somewhat speculative assessment of the problems associated with the stereo‐controlled synthesis of Oligo‐S and to discuss the state‐of‐the‐art in this field including strategies that may lead to Oligo‐S of predetermined chirality. This article is not intended to discourage researchers from further studies of dia‐steromeric mixtures of Oligo‐S as potential pharmaceuticals. Throughout the history of medicinal chemistry numerous useful medicines were discovered, developed, and employed without the detailed knowledge of their structure. Indeed, the composition of the vaccines discovered by Pasteur is a subject of vigorous study still today.
Wild mixtures of stereoisomers are usually formed in the synthesis of oligo(nucleoside phosphorothioate)s owing to the stereogenic phosphorus centers. Is the preparation of isomers with defined configuration at each phosphorus atom feasible, and if so, how far off is the stereoselective synthesis? In this review the problems of the stereoselective preparation of these compounds are outlined, and new synthetic methods are discussed. Oligo(nucleoside phosphorothioate)s have potential as “antisense therapeutics” for treatment of viral infections, cancer, and possibly even AIDS. But medical applications require stereochemically uniform compounds.
Url:
DOI: 10.1002/anie.199407091
Links to Exploration step
ISTEX:62CC846777BBA7A176633D9B711FAA4949EA10E2Le document en format XML
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Stec</name><affiliation><mods:affiliation>Polish Academy of Sciences Centre of Molecular and Macromolecular Studies Department of Bioorganic Chemistry Sienkiewicza 112, PL‐90‐363 Lodz (Poland) Telefax: Int. code +(42)815483</mods:affiliation></affiliation><affiliation><mods:affiliation>Correspondence address: Polish Academy of Sciences Centre of Molecular and Macromolecular Studies Department of Bioorganic Chemistry Sienkiewicza 112, PL‐90‐363 Lodz (Poland) Telefax: Int. code +(42)815483</mods:affiliation></affiliation></author><author><name sortKey="Wilk, Andrzej" sort="Wilk, Andrzej" uniqKey="Wilk A" first="Andrzej" last="Wilk">Andrzej Wilk</name><affiliation><mods:affiliation>Polish Academy of Sciences Centre of Molecular and Macromolecular Studies Department of Bioorganic Chemistry Sienkiewicza 112, PL‐90‐363 Lodz (Poland) Telefax: Int. code +(42)815483</mods:affiliation></affiliation></author></analytic><monogr></monogr><series><title level="j" type="main">Angewandte Chemie International Edition in English</title><title level="j" type="alt">ANGEWANDTE CHEMIE INTERNATIONAL EDITION IN ENGLISH</title><idno type="ISSN">0570-0833</idno><idno type="eISSN">1521-3773</idno><imprint><biblScope unit="vol">33</biblScope><biblScope unit="issue">7</biblScope><biblScope unit="page" from="709">709</biblScope><biblScope unit="page" to="722">722</biblScope><biblScope unit="page-count">14</biblScope><publisher>Hüthig & Wepf Verlag</publisher><pubPlace>Zug</pubPlace><date type="published" when="1994-04-18">1994-04-18</date></imprint><idno type="ISSN">0570-0833</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">0570-0833</idno></seriesStmt></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Encouraging results obtained for modulation of gene expression by antisense oligonucleotides and their analogues have kindled hopes for a new generation of therapeutics against viral infections, cancer, and many other diseases. Among such analogues, oligo(nucleoside phosphorothioate)s (Oligo‐S) have generally shown the highest efficacy in inhibiting the biosynthesis of “unwanted” proteins. The first clinical trials of antisense agents are now in progress using Oligo‐S against genital warts and acute myeloid leukemia, and tests of Oligo‐S against AIDS should follow soon. Nevertheless, their mechanism of action, internalization, cellular trafficking, subcellular localization, and interaction with cellular proteins is still poorly understood. It is assumed a priori that application involves rapid and efficient molecular recognition of target RNA by Oligo‐S; however, the effects of the chirality of Oligo‐S have so far been unappreciated, because Oligo‐S has not yet been synthesized with stereocontrol. Indeed, the diastereomeric composition of Oligo‐S has never been determined, primarily because of the lack of appropriate analytical methods. Since each of the diastereomers is a stereochemically unique chemical entity, questions arise as to which diastereomer is responsible for an observed biological response, including positive (curative) or possibly negative (toxic) side effects. In this review we intend provide a perhaps somewhat speculative assessment of the problems associated with the stereo‐controlled synthesis of Oligo‐S and to discuss the state‐of‐the‐art in this field including strategies that may lead to Oligo‐S of predetermined chirality. This article is not intended to discourage researchers from further studies of dia‐steromeric mixtures of Oligo‐S as potential pharmaceuticals. Throughout the history of medicinal chemistry numerous useful medicines were discovered, developed, and employed without the detailed knowledge of their structure. Indeed, the composition of the vaccines discovered by Pasteur is a subject of vigorous study still today.</div><div type="abstract" xml:lang="en">Wild mixtures of stereoisomers are usually formed in the synthesis of oligo(nucleoside phosphorothioate)s owing to the stereogenic phosphorus centers. Is the preparation of isomers with defined configuration at each phosphorus atom feasible, and if so, how far off is the stereoselective synthesis? In this review the problems of the stereoselective preparation of these compounds are outlined, and new synthetic methods are discussed. Oligo(nucleoside phosphorothioate)s have potential as “antisense therapeutics” for treatment of viral infections, cancer, and possibly even AIDS. 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Among such analogues, oligo(nucleoside phosphorothioate)s (Oligo‐S) have generally shown the highest efficacy in inhibiting the biosynthesis of “unwanted” proteins. The first clinical trials of antisense agents are now in progress using Oligo‐S against genital warts and acute myeloid leukemia, and tests of Oligo‐S against AIDS should follow soon. Nevertheless, their mechanism of action, internalization, cellular trafficking, subcellular localization, and interaction with cellular proteins is still poorly understood. It is assumed a priori that application involves rapid and efficient molecular recognition of target RNA by Oligo‐S; however, the effects of the chirality of Oligo‐S have so far been unappreciated, because Oligo‐S has not yet been synthesized with stereocontrol. Indeed, the diastereomeric composition of Oligo‐S has never been determined, primarily because of the lack of appropriate analytical methods. Since each of the diastereomers is a stereochemically unique chemical entity, questions arise as to which diastereomer is responsible for an observed biological response, including positive (curative) or possibly negative (toxic) side effects. In this review we intend provide a perhaps somewhat speculative assessment of the problems associated with the stereo‐controlled synthesis of Oligo‐S and to discuss the state‐of‐the‐art in this field including strategies that may lead to Oligo‐S of predetermined chirality. This article is not intended to discourage researchers from further studies of dia‐steromeric mixtures of Oligo‐S as potential pharmaceuticals. Throughout the history of medicinal chemistry numerous useful medicines were discovered, developed, and employed without the detailed knowledge of their structure. 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Blaszczyk</json:string><json:string>J. F. Marlier</json:string></persName><placeName><json:string>Foster City</json:string><json:string>Poland</json:string><json:string>Amsterdam</json:string><json:string>CA</json:string><json:string>York</json:string></placeName><ref_url></ref_url><ref_bibl><json:string>Grajkowski et al.</json:string><json:string>[61]</json:string><json:string>Eckstein et al.</json:string><json:string>[34]</json:string><json:string>Battistini et al.</json:string><json:string>Lebedev et al.</json:string><json:string>[44]</json:string><json:string>Lesnikowski et al.</json:string><json:string>University of Lodz, 1992</json:string><json:string>[49]</json:string><json:string>Okruszek et al.</json:string><json:string>[59]</json:string><json:string>Ohtsuka et al.</json:string><json:string>[41]</json:string><json:string>[47]</json:string><json:string>Hata et al.</json:string></ref_bibl><bibl></bibl></unitex></namedEntities><ark><json:string>ark:/67375/WNG-WW269FP3-T</json:string></ark><categories><inist><json:string>1 - sciences appliquees, technologies et medecines</json:string><json:string>2 - sciences biologiques et medicales</json:string><json:string>3 - sciences biologiques fondamentales et appliquees. psychologie</json:string></inist></categories><publicationDate>1994</publicationDate><copyrightDate>1994</copyrightDate><doi><json:string>10.1002/anie.199407091</json:string></doi><id>62CC846777BBA7A176633D9B711FAA4949EA10E2</id><score>1</score><fulltext><json:item><extension>pdf</extension><original>true</original><mimetype>application/pdf</mimetype><uri>https://api.istex.fr/ark:/67375/WNG-WW269FP3-T/fulltext.pdf</uri></json:item><json:item><extension>zip</extension><original>false</original><mimetype>application/zip</mimetype><uri>https://api.istex.fr/ark:/67375/WNG-WW269FP3-T/bundle.zip</uri></json:item><istex:fulltextTEI uri="https://api.istex.fr/ark:/67375/WNG-WW269FP3-T/fulltext.tei"><teiHeader><fileDesc><titleStmt><title level="a" type="main">Stereocontrolled Synthesis of Oligo(nucleoside phosphorothioate)s</title></titleStmt><publicationStmt><authority>ISTEX</authority><publisher>Hüthig & Wepf Verlag</publisher><pubPlace>Zug</pubPlace><availability><licence>Copyright © 1994 by VCH Verlagsgesellschaft mbH, Germany</licence></availability><date type="published" when="1994-04-18"></date></publicationStmt><notesStmt><note type="content-type" subtype="review-article" source="reviewArticle" scheme="https://content-type.data.istex.fr/ark:/67375/XTP-L5L7X3NF-P">review-article</note><note type="publication-type" subtype="journal" scheme="https://publication-type.data.istex.fr/ark:/67375/JMC-0GLKJH51-B">journal</note></notesStmt><sourceDesc><biblStruct type="review-article"><analytic><title level="a" type="main">Stereocontrolled Synthesis of Oligo(nucleoside phosphorothioate)s</title><author xml:id="author-0000" role="corresp"><persName><addName>Prof. Dr.</addName><forename type="first">Wojciech J.</forename><surname>Stec</surname></persName><affiliation><orgName type="institution">Polish Academy of Sciences Centre of Molecular and Macromolecular Studies Department of Bioorganic Chemistry Sienkiewicza 112</orgName><address><addrLine>PL‐90‐363 Lodz (Poland) Telefax: Int. code +(42)815483</addrLine><country key="PL" xml:lang="en">POLAND</country></address></affiliation></author><author xml:id="author-0001"><persName><addName>Dr.</addName><forename type="first">Andrzej</forename><surname>Wilk</surname></persName><affiliation><orgName type="institution">Polish Academy of Sciences Centre of Molecular and Macromolecular Studies Department of Bioorganic Chemistry Sienkiewicza 112</orgName><address><addrLine>PL‐90‐363 Lodz (Poland) Telefax: Int. code +(42)815483</addrLine><country key="PL" xml:lang="en">POLAND</country></address></affiliation></author><idno type="istex">62CC846777BBA7A176633D9B711FAA4949EA10E2</idno><idno type="ark">ark:/67375/WNG-WW269FP3-T</idno><idno type="DOI">10.1002/anie.199407091</idno><idno type="unit">ANIE199407091</idno><idno type="toTypesetVersion">file:ANIEBACK.ANIE199407091.pdf</idno></analytic><monogr><title level="j" type="main">Angewandte Chemie International Edition in English</title><title level="j" type="alt">ANGEWANDTE CHEMIE INTERNATIONAL EDITION IN ENGLISH</title><idno type="pISSN">0570-0833</idno><idno type="eISSN">1521-3773</idno><idno type="book-DOI">10.1002/(ISSN)1521-3773a</idno><idno type="book-part-DOI">10.1002/anie.v33:7</idno><idno type="product">ANIEBACK</idno><imprint><biblScope unit="vol">33</biblScope><biblScope unit="issue">7</biblScope><biblScope unit="page" from="709">709</biblScope><biblScope unit="page" to="722">722</biblScope><biblScope unit="page-count">14</biblScope><publisher>Hüthig & Wepf Verlag</publisher><pubPlace>Zug</pubPlace><date type="published" when="1994-04-18"></date></imprint></monogr></biblStruct></sourceDesc></fileDesc><encodingDesc><schemaRef type="ODD" url="https://xml-schema.delivery.istex.fr/tei-istex.odd"></schemaRef><appInfo><application ident="pub2tei" version="1.0.10" when="2019-12-20"><label>pub2TEI-ISTEX</label><desc>A set of style sheets for converting XML documents encoded in various scientific publisher formats into a common TEI format.
<ref target="http://www.tei-c.org/">We use TEI</ref></desc></application></appInfo></encodingDesc><profileDesc><abstract xml:lang="en" style="main"><head>Abstract</head><p>Encouraging results obtained for modulation of gene expression by antisense oligonucleotides and their analogues have kindled hopes for a new generation of therapeutics against viral infections, cancer, and many other diseases. Among such analogues, oligo(nucleoside phosphorothioate)s (Oligo‐S) have generally shown the highest efficacy in inhibiting the biosynthesis of “unwanted” proteins. The first clinical trials of antisense agents are now in progress using Oligo‐S against genital warts and acute myeloid leukemia, and tests of Oligo‐S against AIDS should follow soon. Nevertheless, their mechanism of action, internalization, cellular trafficking, subcellular localization, and interaction with cellular proteins is still poorly understood. It is assumed a priori that application involves rapid and efficient molecular recognition of target RNA by Oligo‐S; however, the effects of the chirality of Oligo‐S have so far been unappreciated, because Oligo‐S has not yet been synthesized with stereocontrol. Indeed, the diastereomeric composition of Oligo‐S has never been determined, primarily because of the lack of appropriate analytical methods. Since each of the diastereomers is a stereochemically unique chemical entity, questions arise as to which diastereomer is responsible for an observed biological response, including positive (curative) or possibly negative (toxic) side effects.</p><p>In this review we intend provide a perhaps somewhat speculative assessment of the problems associated with the stereo‐controlled synthesis of Oligo‐S and to discuss the state‐of‐the‐art in this field including strategies that may lead to Oligo‐S of predetermined chirality. This article is not intended to discourage researchers from further studies of dia‐steromeric mixtures of Oligo‐S as potential pharmaceuticals. Throughout the history of medicinal chemistry numerous useful medicines were discovered, developed, and employed without the detailed knowledge of their structure. Indeed, the composition of the vaccines discovered by Pasteur is a subject of vigorous study still today.</p></abstract><abstract xml:lang="en" style="short"><p><hi rend="bold">Wild mixtures of stereoisomers</hi> are usually formed in the synthesis of oligo(nucleoside phosphorothioate)s owing to the stereogenic phosphorus centers. Is the preparation of isomers with defined configuration at each phosphorus atom feasible, and if so, how far off is the stereoselective synthesis? In this review the problems of the stereoselective preparation of these compounds are outlined, and new synthetic methods are discussed. Oligo(nucleoside phosphorothioate)s have potential as “antisense therapeutics” for treatment of viral infections, cancer, and possibly even AIDS. 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Engl.</title></titleGroup></publicationMeta><publicationMeta level="part" position="70"><doi origin="wiley" registered="yes">10.1002/anie.v33:7</doi><numberingGroup><numbering type="journalVolume" number="33">33</numbering><numbering type="journalIssue">7</numbering></numberingGroup><coverDate startDate="1994-04-18">April 18, 1994</coverDate></publicationMeta><publicationMeta level="unit" type="reviewArticle" position="3" status="forIssue"><doi origin="wiley" registered="yes">10.1002/anie.199407091</doi><idGroup><id type="unit" value="ANIE199407091"></id></idGroup><countGroup><count type="pageTotal" number="14"></count></countGroup><titleGroup><title type="articleCategory">Review</title><title type="tocHeading1">Reviews</title></titleGroup><copyright ownership="publisher">Copyright © 1994 by VCH Verlagsgesellschaft mbH, Germany</copyright><eventGroup><event type="manuscriptReceived" date="1993-02-12"></event><event type="firstOnline" date="2003-12-22"></event><event type="publishedOnlineFinalForm" date="2003-12-22"></event><event type="xmlConverted" agent="Converter:JWSART34_TO_WML3G version:2.3.2 mode:FullText source:HeaderRef result:HeaderRef" date="2010-03-09"></event><event type="xmlConverted" agent="Converter:WILEY_ML3G_TO_WILEY_ML3GV2 version:3.8.8" date="2014-01-24"></event><event type="xmlConverted" agent="Converter:WML3G_To_WML3G version:4.1.7 mode:FullText,remove_FC" date="2014-10-14"></event></eventGroup><numberingGroup><numbering type="pageFirst">709</numbering><numbering type="pageLast">722</numbering></numberingGroup><correspondenceTo>Polish Academy of Sciences Centre of Molecular and Macromolecular Studies Department of Bioorganic Chemistry Sienkiewicza 112, PL‐90‐363 Lodz (Poland) Telefax: Int. code +(42)815483</correspondenceTo><linkGroup><link type="toTypesetVersion" href="file:ANIEBACK.ANIE199407091.pdf"></link></linkGroup></publicationMeta><contentMeta><countGroup><count type="figureTotal" number="5"></count><count type="tableTotal" number="1"></count><count type="referenceTotal" number="72"></count></countGroup><titleGroup><title type="main" xml:lang="en">Stereocontrolled Synthesis of Oligo(nucleoside phosphorothioate)s</title></titleGroup><creators><creator xml:id="au1" creatorRole="author" affiliationRef="#af1" corresponding="yes"><personName><honorifics>Prof. Dr.</honorifics><givenNames>Wojciech J.</givenNames><familyName>Stec</familyName></personName></creator><creator xml:id="au2" creatorRole="author" affiliationRef="#af1"><personName><honorifics>Dr.</honorifics><givenNames>Andrzej</givenNames><familyName>Wilk</familyName></personName></creator></creators><affiliationGroup><affiliation xml:id="af1" countryCode="PL" type="organization"><unparsedAffiliation>Polish Academy of Sciences Centre of Molecular and Macromolecular Studies Department of Bioorganic Chemistry Sienkiewicza 112, PL‐90‐363 Lodz (Poland) Telefax: Int. code +(42)815483</unparsedAffiliation></affiliation></affiliationGroup><keywordGroup xml:lang="en" type="author"><keyword xml:id="kwd1">Drug research</keyword><keyword xml:id="kwd2">Nucleosides</keyword><keyword xml:id="kwd3">Phosphorothioates</keyword><keyword xml:id="kwd4">Medicinal chemistry</keyword></keywordGroup><abstractGroup><abstract type="main" xml:lang="en"><title type="main">Abstract</title><p>Encouraging results obtained for modulation of gene expression by antisense oligonucleotides and their analogues have kindled hopes for a new generation of therapeutics against viral infections, cancer, and many other diseases. Among such analogues, oligo(nucleoside phosphorothioate)s (Oligo‐S) have generally shown the highest efficacy in inhibiting the biosynthesis of “unwanted” proteins. The first clinical trials of antisense agents are now in progress using Oligo‐S against genital warts and acute myeloid leukemia, and tests of Oligo‐S against AIDS should follow soon. Nevertheless, their mechanism of action, internalization, cellular trafficking, subcellular localization, and interaction with cellular proteins is still poorly understood. It is assumed a priori that application involves rapid and efficient molecular recognition of target RNA by Oligo‐S; however, the effects of the chirality of Oligo‐S have so far been unappreciated, because Oligo‐S has not yet been synthesized with stereocontrol. Indeed, the diastereomeric composition of Oligo‐S has never been determined, primarily because of the lack of appropriate analytical methods. Since each of the diastereomers is a stereochemically unique chemical entity, questions arise as to which diastereomer is responsible for an observed biological response, including positive (curative) or possibly negative (toxic) side effects.</p><p>In this review we intend provide a perhaps somewhat speculative assessment of the problems associated with the stereo‐controlled synthesis of Oligo‐S and to discuss the state‐of‐the‐art in this field including strategies that may lead to Oligo‐S of predetermined chirality. This article is not intended to discourage researchers from further studies of dia‐steromeric mixtures of Oligo‐S as potential pharmaceuticals. Throughout the history of medicinal chemistry numerous useful medicines were discovered, developed, and employed without the detailed knowledge of their structure. Indeed, the composition of the vaccines discovered by Pasteur is a subject of vigorous study still today.</p></abstract><abstract type="short" xml:lang="en"><p><b>Wild mixtures of stereoisomers</b> are usually formed in the synthesis of oligo(nucleoside phosphorothioate)s owing to the stereogenic phosphorus centers. Is the preparation of isomers with defined configuration at each phosphorus atom feasible, and if so, how far off is the stereoselective synthesis? In this review the problems of the stereoselective preparation of these compounds are outlined, and new synthetic methods are discussed. Oligo(nucleoside phosphorothioate)s have potential as “antisense therapeutics” for treatment of viral infections, cancer, and possibly even AIDS. But medical applications require stereochemically uniform compounds.</p></abstract></abstractGroup></contentMeta></header></component></istex:document></istex:metadataXml><mods version="3.6"><titleInfo lang="en"><title>Stereocontrolled Synthesis of Oligo(nucleoside phosphorothioate)s</title></titleInfo><titleInfo type="alternative" contentType="CDATA" lang="en"><title>Stereocontrolled Synthesis of Oligo(nucleoside phosphorothioate)s</title></titleInfo><name type="personal"><namePart type="termsOfAddress">Prof. Dr.</namePart><namePart type="given">Wojciech J.</namePart><namePart type="family">Stec</namePart><affiliation>Polish Academy of Sciences Centre of Molecular and Macromolecular Studies Department of Bioorganic Chemistry Sienkiewicza 112, PL‐90‐363 Lodz (Poland) Telefax: Int. code +(42)815483</affiliation><affiliation>Correspondence address: Polish Academy of Sciences Centre of Molecular and Macromolecular Studies Department of Bioorganic Chemistry Sienkiewicza 112, PL‐90‐363 Lodz (Poland) Telefax: Int. code +(42)815483</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="termsOfAddress">Dr.</namePart><namePart type="given">Andrzej</namePart><namePart type="family">Wilk</namePart><affiliation>Polish Academy of Sciences Centre of Molecular and Macromolecular Studies Department of Bioorganic Chemistry Sienkiewicza 112, PL‐90‐363 Lodz (Poland) Telefax: Int. code +(42)815483</affiliation><role><roleTerm type="text">author</roleTerm></role></name><typeOfResource>text</typeOfResource><genre type="review-article" displayLabel="reviewArticle" authority="ISTEX" authorityURI="https://content-type.data.istex.fr" valueURI="https://content-type.data.istex.fr/ark:/67375/XTP-L5L7X3NF-P">review-article</genre><originInfo><publisher>Hüthig & Wepf Verlag</publisher><place><placeTerm type="text">Zug</placeTerm></place><dateIssued encoding="w3cdtf">1994-04-18</dateIssued><dateCaptured encoding="w3cdtf">1993-02-12</dateCaptured><copyrightDate encoding="w3cdtf">1994</copyrightDate></originInfo><language><languageTerm type="code" authority="rfc3066">en</languageTerm><languageTerm type="code" authority="iso639-2b">eng</languageTerm></language><physicalDescription><extent unit="figures">5</extent><extent unit="tables">1</extent><extent unit="references">72</extent></physicalDescription><abstract lang="en">Encouraging results obtained for modulation of gene expression by antisense oligonucleotides and their analogues have kindled hopes for a new generation of therapeutics against viral infections, cancer, and many other diseases. Among such analogues, oligo(nucleoside phosphorothioate)s (Oligo‐S) have generally shown the highest efficacy in inhibiting the biosynthesis of “unwanted” proteins. The first clinical trials of antisense agents are now in progress using Oligo‐S against genital warts and acute myeloid leukemia, and tests of Oligo‐S against AIDS should follow soon. Nevertheless, their mechanism of action, internalization, cellular trafficking, subcellular localization, and interaction with cellular proteins is still poorly understood. It is assumed a priori that application involves rapid and efficient molecular recognition of target RNA by Oligo‐S; however, the effects of the chirality of Oligo‐S have so far been unappreciated, because Oligo‐S has not yet been synthesized with stereocontrol. Indeed, the diastereomeric composition of Oligo‐S has never been determined, primarily because of the lack of appropriate analytical methods. Since each of the diastereomers is a stereochemically unique chemical entity, questions arise as to which diastereomer is responsible for an observed biological response, including positive (curative) or possibly negative (toxic) side effects. In this review we intend provide a perhaps somewhat speculative assessment of the problems associated with the stereo‐controlled synthesis of Oligo‐S and to discuss the state‐of‐the‐art in this field including strategies that may lead to Oligo‐S of predetermined chirality. This article is not intended to discourage researchers from further studies of dia‐steromeric mixtures of Oligo‐S as potential pharmaceuticals. Throughout the history of medicinal chemistry numerous useful medicines were discovered, developed, and employed without the detailed knowledge of their structure. Indeed, the composition of the vaccines discovered by Pasteur is a subject of vigorous study still today.</abstract><abstract type="short" lang="en">Wild mixtures of stereoisomers are usually formed in the synthesis of oligo(nucleoside phosphorothioate)s owing to the stereogenic phosphorus centers. Is the preparation of isomers with defined configuration at each phosphorus atom feasible, and if so, how far off is the stereoselective synthesis? In this review the problems of the stereoselective preparation of these compounds are outlined, and new synthetic methods are discussed. Oligo(nucleoside phosphorothioate)s have potential as “antisense therapeutics” for treatment of viral infections, cancer, and possibly even AIDS. But medical applications require stereochemically uniform compounds.</abstract><subject lang="en"><genre>keywords</genre><topic>Drug research</topic><topic>Nucleosides</topic><topic>Phosphorothioates</topic><topic>Medicinal chemistry</topic></subject><relatedItem type="host"><titleInfo><title>Angewandte Chemie International Edition in English</title></titleInfo><titleInfo type="abbreviated"><title>Angew. Chem. Int. Ed. 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J.</namePart><namePart type="family">Stec</namePart><role><roleTerm type="text">author</roleTerm></role></name><part><date>1982</date><detail type="volume"><caption>vol.</caption><number>23</number></detail><extent unit="pages"><start>4289</start></extent></part></relatedItem><identifier type="istex">62CC846777BBA7A176633D9B711FAA4949EA10E2</identifier><identifier type="ark">ark:/67375/WNG-WW269FP3-T</identifier><identifier type="DOI">10.1002/anie.199407091</identifier><identifier type="ArticleID">ANIE199407091</identifier><accessCondition type="use and reproduction" contentType="copyright">Copyright © 1994 by VCH Verlagsgesellschaft mbH, Germany</accessCondition><recordInfo><recordContentSource authority="ISTEX" authorityURI="https://loaded-corpus.data.istex.fr" valueURI="https://loaded-corpus.data.istex.fr/ark:/67375/XBH-L0C46X92-X">wiley</recordContentSource><recordOrigin>Converted from (version ) to MODS version 3.6.</recordOrigin><recordCreationDate encoding="w3cdtf">2019-11-13</recordCreationDate></recordInfo></mods><json:item><extension>json</extension><original>false</original><mimetype>application/json</mimetype><uri>https://api.istex.fr/ark:/67375/WNG-WW269FP3-T/record.json</uri></json:item></metadata><serie></serie></istex></record>Pour manipuler ce document sous Unix (Dilib)
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