Photolabile group for 5′-OH protection of nucleosides: synthesis and photodeprotection rate
Identifieur interne : 000054 ( Istex/Corpus ); précédent : 000053; suivant : 000055Photolabile group for 5′-OH protection of nucleosides: synthesis and photodeprotection rate
Auteurs : P. Berroy ; M. L. Viriot ; M. C. CarréSource :
- Sensors & Actuators: B. Chemical [ 0925-4005 ] ; 2001.
English descriptors
- KwdEn :
- Actuator, Berroy, Chem, Chemical actinometry, Chemical engineering school, DNA array, Daibu, Deoxyadenosine, Deoxynucleosides, Elsevier science, Light intensity, Menpoc, Menpoc group, Mnppoc, Mnppoc group, Mnppoh, Molar extinction coefficient, Nucleoside, Oligonucleotide, Oligonucleotide synthesis, Peak area, Photochemical cleavage, Photolabile, Photolabile group, Photolabile groups, Photolysis, Photolytic, Photolytic properties, Protection of deoxynucleosides, Quantum yields.
- Teeft :
- Actuator, Berroy, Chem, Chemical actinometry, Chemical engineering school, Daibu, Deoxyadenosine, Deoxynucleosides, Elsevier science, Light intensity, Menpoc, Menpoc group, Mnppoc, Mnppoc group, Mnppoh, Molar extinction coefficient, Nucleoside, Oligonucleotide, Oligonucleotide synthesis, Peak area, Photochemical cleavage, Photolabile, Photolabile group, Photolabile groups, Photolysis, Photolytic, Photolytic properties, Quantum yields.
Abstract
Abstract: In this paper, we described the properties of a new photolabile group, 2-(3,4-methylenedioxy-6-nitrophenyl)propoxycarbonyl, MNPPOC. In spite of moderate yields of synthesis, photolytic properties could be analyzed for 5′-OH protected T and dAiBu. The half-lives (t1/2) 11 and 12s were found, respectively, with a good recovery of the corresponding deprotected deoxynucleoside (95–99%). The photolysis rate of this new photolabile group was five-fold faster than the MeNPOC one.
Url:
DOI: 10.1016/S0925-4005(00)00731-0
Links to Exploration step
ISTEX:761D978B0FBD55D0ACAA8D2961609C48C8E91116Le document en format XML
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In spite of moderate yields of synthesis, photolytic properties could be analyzed for 5′-OH protected T and dAiBu. The half-lives (t1/2) 11 and 12s were found, respectively, with a good recovery of the corresponding deprotected deoxynucleoside (95–99%). 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In spite of moderate yields of synthesis, photolytic properties could be analyzed for 5′-OH protected T and dAiBu. The half-lives (t1/2) 11 and 12s were found, respectively, with a good recovery of the corresponding deprotected deoxynucleoside (95–99%). The photolysis rate of this new photolabile group was five-fold faster than the MeNPOC one.</abstract><qualityIndicators><score>2.37</score><pdfVersion>1.2</pdfVersion><pdfPageSize>595 x 794 pts</pdfPageSize><refBibsNative>true</refBibsNative><keywordCount>4</keywordCount><abstractCharCount>477</abstractCharCount><pdfWordCount>1578</pdfWordCount><pdfCharCount>10373</pdfCharCount><pdfPageCount>4</pdfPageCount><abstractWordCount>66</abstractWordCount></qualityIndicators><title>Photolabile group for 5′-OH protection of nucleosides: synthesis and photodeprotection rate</title><pii><json:string>S0925-4005(00)00731-0</json:string></pii><genre><json:string>research-article</json:string></genre><host><title>Sensors & Actuators: B. 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Jaffrezic-Renault</name></json:item></editor></host><categories><wos><json:string>science</json:string><json:string>instruments & instrumentation</json:string><json:string>electrochemistry</json:string><json:string>chemistry, analytical</json:string></wos><scienceMetrix><json:string>natural sciences</json:string><json:string>chemistry</json:string><json:string>analytical chemistry</json:string></scienceMetrix><inist><json:string>sciences appliquees, technologies et medecines</json:string><json:string>sciences biologiques et medicales</json:string><json:string>sciences medicales</json:string><json:string>gynecologie. andrologie. obstetrique</json:string></inist></categories><publicationDate>2001</publicationDate><copyrightDate>2001</copyrightDate><doi><json:string>10.1016/S0925-4005(00)00731-0</json:string></doi><id>761D978B0FBD55D0ACAA8D2961609C48C8E91116</id><score>1</score><fulltext><json:item><extension>pdf</extension><original>true</original><mimetype>application/pdf</mimetype><uri>https://api.istex.fr/document/761D978B0FBD55D0ACAA8D2961609C48C8E91116/fulltext/pdf</uri></json:item><json:item><extension>zip</extension><original>false</original><mimetype>application/zip</mimetype><uri>https://api.istex.fr/document/761D978B0FBD55D0ACAA8D2961609C48C8E91116/fulltext/zip</uri></json:item><istex:fulltextTEI uri="https://api.istex.fr/document/761D978B0FBD55D0ACAA8D2961609C48C8E91116/fulltext/tei"><teiHeader><fileDesc><titleStmt><title level="a" type="main" xml:lang="en">Photolabile group for 5′-OH protection of nucleosides: synthesis and photodeprotection rate</title></titleStmt><publicationStmt><authority>ISTEX</authority><publisher>ELSEVIER</publisher><availability><p>©2001 Elsevier Science B.V.</p></availability><date>2001</date></publicationStmt><notesStmt><note type="content">Fig. 1: Synthetic scheme for 5′-O-MNPPOC protected deoxynucleosides T and dAiBu. Reagents: (a) 70% HNO3, 10–15°C, 1h; (b) (i) MeOCH2P+Ph3Cl−, BuLi, THF, 0°C, 20min, (ii) 0°C, 1.5h; (c) HCl 6N/ CH3CN v/v 1/1, RT, 1h; (d) NaBH4, MeOH, RT, 1h; (e) (i) Cl3COCOOCCl3, CH2Cl2, 0°C, 1h, (ii) pyridine, −15°C, 45min then at RT overnight.</note><note type="content">Fig. 2: Absorption spectra: normed curves.</note><note type="content">Fig. 3: Photolysis of MeNPOC-T and MNPPOC-T.</note><note type="content">Fig. 4: Photolysis of MeNPOC-dAiBu and MNPPOC-dAiBu.</note><note type="content">Table 1: Photolysis data for 5′-O-protected T and dAiBua</note></notesStmt><sourceDesc><biblStruct type="inbook"><analytic><title level="a" type="main" xml:lang="en">Photolabile group for 5′-OH protection of nucleosides: synthesis and photodeprotection rate</title><author xml:id="author-0000"><persName><forename type="first">P.</forename><surname>Berroy</surname></persName><affiliation>Département de Chimie Physique des Réactions, GRAPP, UMR 7630 CNRS-INPL, Groupe ENSIC, 1, rue Grandville, 54000 Nancy, France</affiliation></author><author xml:id="author-0001"><persName><forename type="first">M.L.</forename><surname>Viriot</surname></persName><affiliation>Département de Chimie Physique des Réactions, GRAPP, UMR 7630 CNRS-INPL, Groupe ENSIC, 1, rue Grandville, 54000 Nancy, France</affiliation></author><author xml:id="author-0002"><persName><forename type="first">M.C.</forename><surname>Carré</surname></persName><email>marie-christiane.carre@ensic.inpl-nancy.fr</email><note type="correspondence"><p>Corresponding author. Fax: +33-3-83-32-10-99</p></note><affiliation>Département de Chimie Physique des Réactions, GRAPP, UMR 7630 CNRS-INPL, Groupe ENSIC, 1, rue Grandville, 54000 Nancy, France</affiliation></author><idno type="istex">761D978B0FBD55D0ACAA8D2961609C48C8E91116</idno><idno type="DOI">10.1016/S0925-4005(00)00731-0</idno><idno type="PII">S0925-4005(00)00731-0</idno></analytic><monogr><title level="j">Sensors & Actuators: B. Chemical</title><title level="j" type="abbrev">SNB</title><idno type="pISSN">0925-4005</idno><idno type="PII">S0925-4005(00)X0073-1</idno><meeting><addName>Proceedings of the 5th European Conference on Optical Chemical Sensors and Biosensors, Lyon-Villeurbanne, France</addName><addName>EUROPT(R)ODE V S.I.</addName><date>20000416</date><date>20000419</date></meeting><editor xml:id="book-author-0000"><persName>Prof. P.R. Coulet and Dr. N. Jaffrezic-Renault</persName></editor><imprint><publisher>ELSEVIER</publisher><date type="published" when="2001"></date><biblScope unit="volume">74</biblScope><biblScope unit="issue">1–3</biblScope><biblScope unit="page" from="186">186</biblScope><biblScope unit="page" to="189">189</biblScope></imprint></monogr></biblStruct></sourceDesc></fileDesc><profileDesc><creation><date>2001</date></creation><langUsage><language ident="en">en</language></langUsage><abstract xml:lang="en"><p>In this paper, we described the properties of a new photolabile group, 2-(3,4-methylenedioxy-6-nitrophenyl)propoxycarbonyl, MNPPOC. In spite of moderate yields of synthesis, photolytic properties could be analyzed for 5′-OH protected T and dAiBu. The half-lives (t1/2) 11 and 12s were found, respectively, with a good recovery of the corresponding deprotected deoxynucleoside (95–99%). The photolysis rate of this new photolabile group was five-fold faster than the MeNPOC one.</p></abstract><textClass xml:lang="en"><keywords scheme="keyword"><list><head>Keywords</head><item><term>Photolabile groups</term></item><item><term>Protection of deoxynucleosides</term></item><item><term>Photolysis</term></item><item><term>DNA array</term></item></list></keywords></textClass></profileDesc><revisionDesc><change when="2001">Published</change></revisionDesc></teiHeader></istex:fulltextTEI><json:item><extension>txt</extension><original>false</original><mimetype>text/plain</mimetype><uri>https://api.istex.fr/document/761D978B0FBD55D0ACAA8D2961609C48C8E91116/fulltext/txt</uri></json:item></fulltext><metadata><istex:metadataXml wicri:clean="Elsevier, elements deleted: ce:floats; body; tail"><istex:xmlDeclaration>version="1.0" encoding="utf-8"</istex:xmlDeclaration><istex:docType PUBLIC="-//ES//DTD journal article DTD version 4.5.2//EN//XML" URI="art452.dtd" name="istex:docType"><istex:entity SYSTEM="gr1" NDATA="IMAGE" name="gr1"></istex:entity><istex:entity SYSTEM="gr2" NDATA="IMAGE" name="gr2"></istex:entity><istex:entity SYSTEM="gr3" NDATA="IMAGE" name="gr3"></istex:entity><istex:entity SYSTEM="gr4" NDATA="IMAGE" name="gr4"></istex:entity></istex:docType><istex:document><converted-article version="4.5.2" docsubtype="fla" xml:lang="en"><item-info><jid>SNB</jid><aid>3680</aid><ce:pii>S0925-4005(00)00731-0</ce:pii><ce:doi>10.1016/S0925-4005(00)00731-0</ce:doi><ce:copyright type="full-transfer" year="2001">Elsevier Science B.V.</ce:copyright></item-info><head><ce:title>Photolabile group for 5′-OH protection of nucleosides: synthesis and photodeprotection rate</ce:title><ce:author-group><ce:author biographyid="BIO1"><ce:given-name>P.</ce:given-name><ce:surname>Berroy</ce:surname></ce:author><ce:author biographyid="BIO2"><ce:given-name>M.L.</ce:given-name><ce:surname>Viriot</ce:surname></ce:author><ce:author biographyid="BIO3"><ce:given-name>M.C.</ce:given-name><ce:surname>Carré</ce:surname><ce:cross-ref refid="CORR1">*</ce:cross-ref><ce:e-address>marie-christiane.carre@ensic.inpl-nancy.fr</ce:e-address></ce:author><ce:affiliation><ce:textfn>Département de Chimie Physique des Réactions, GRAPP, UMR 7630 CNRS-INPL, Groupe ENSIC, 1, rue Grandville, 54000 Nancy, France</ce:textfn></ce:affiliation><ce:correspondence id="CORR1"><ce:label>*</ce:label><ce:text>Corresponding author. Fax: +33-3-83-32-10-99</ce:text></ce:correspondence></ce:author-group><ce:abstract><ce:section-title>Abstract</ce:section-title><ce:abstract-sec><ce:simple-para>In this paper, we described the properties of a new photolabile group, 2-(3,4-methylenedioxy-6-nitrophenyl)propoxycarbonyl, MNPPOC. In spite of moderate yields of synthesis, photolytic properties could be analyzed for 5′-OH protected T and dA<ce:sup><ce:italic>i</ce:italic>Bu</ce:sup>. The half-lives (<ce:italic>t</ce:italic><ce:inf>1/2</ce:inf>) 11 and 12<ce:hsp sp="0.25"></ce:hsp>s were found, respectively, with a good recovery of the corresponding deprotected deoxynucleoside (95–99%). The photolysis rate of this new photolabile group was five-fold faster than the MeNPOC one.</ce:simple-para></ce:abstract-sec></ce:abstract><ce:keywords class="keyword" xml:lang="en"><ce:section-title>Keywords</ce:section-title><ce:keyword><ce:text>Photolabile groups</ce:text></ce:keyword><ce:keyword><ce:text>Protection of deoxynucleosides</ce:text></ce:keyword><ce:keyword><ce:text>Photolysis</ce:text></ce:keyword><ce:keyword><ce:text>DNA array</ce:text></ce:keyword></ce:keywords></head></converted-article></istex:document></istex:metadataXml><mods version="3.6"><titleInfo lang="en"><title>Photolabile group for 5′-OH protection of nucleosides: synthesis and photodeprotection rate</title></titleInfo><titleInfo type="alternative" lang="en" contentType="CDATA"><title>Photolabile group for 5′-OH protection of nucleosides: synthesis and photodeprotection rate</title></titleInfo><name type="personal"><namePart type="given">P.</namePart><namePart type="family">Berroy</namePart><affiliation>Département de Chimie Physique des Réactions, GRAPP, UMR 7630 CNRS-INPL, Groupe ENSIC, 1, rue Grandville, 54000 Nancy, France</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">M.L.</namePart><namePart type="family">Viriot</namePart><affiliation>Département de Chimie Physique des Réactions, GRAPP, UMR 7630 CNRS-INPL, Groupe ENSIC, 1, rue Grandville, 54000 Nancy, France</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">M.C.</namePart><namePart type="family">Carré</namePart><affiliation>Département de Chimie Physique des Réactions, GRAPP, UMR 7630 CNRS-INPL, Groupe ENSIC, 1, rue Grandville, 54000 Nancy, France</affiliation><affiliation>E-mail: marie-christiane.carre@ensic.inpl-nancy.fr</affiliation><description>Corresponding author. Fax: +33-3-83-32-10-99</description><role><roleTerm type="text">author</roleTerm></role></name><typeOfResource>text</typeOfResource><genre type="research-article" displayLabel="Full-length article" authority="ISTEX" authorityURI="https://content-type.data.istex.fr" valueURI="https://content-type.data.istex.fr/ark:/67375/XTP-1JC4F85T-7">research-article</genre><originInfo><publisher>ELSEVIER</publisher><dateIssued encoding="w3cdtf">2001</dateIssued><copyrightDate encoding="w3cdtf">2001</copyrightDate></originInfo><language><languageTerm type="code" authority="iso639-2b">eng</languageTerm><languageTerm type="code" authority="rfc3066">en</languageTerm></language><abstract lang="en">Abstract: In this paper, we described the properties of a new photolabile group, 2-(3,4-methylenedioxy-6-nitrophenyl)propoxycarbonyl, MNPPOC. In spite of moderate yields of synthesis, photolytic properties could be analyzed for 5′-OH protected T and dAiBu. The half-lives (t1/2) 11 and 12s were found, respectively, with a good recovery of the corresponding deprotected deoxynucleoside (95–99%). The photolysis rate of this new photolabile group was five-fold faster than the MeNPOC one.</abstract><note type="content">Fig. 1: Synthetic scheme for 5′-O-MNPPOC protected deoxynucleosides T and dAiBu. Reagents: (a) 70% HNO3, 10–15°C, 1h; (b) (i) MeOCH2P+Ph3Cl−, BuLi, THF, 0°C, 20min, (ii) 0°C, 1.5h; (c) HCl 6N/ CH3CN v/v 1/1, RT, 1h; (d) NaBH4, MeOH, RT, 1h; (e) (i) Cl3COCOOCCl3, CH2Cl2, 0°C, 1h, (ii) pyridine, −15°C, 45min then at RT overnight.</note><note type="content">Fig. 2: Absorption spectra: normed curves.</note><note type="content">Fig. 3: Photolysis of MeNPOC-T and MNPPOC-T.</note><note type="content">Fig. 4: Photolysis of MeNPOC-dAiBu and MNPPOC-dAiBu.</note><note type="content">Table 1: Photolysis data for 5′-O-protected T and dAiBua</note><subject lang="en"><genre>Keywords</genre><topic>Photolabile groups</topic><topic>Protection of deoxynucleosides</topic><topic>Photolysis</topic><topic>DNA array</topic></subject><relatedItem type="host"><titleInfo><title>Sensors & Actuators: B. Chemical</title></titleInfo><titleInfo type="abbreviated"><title>SNB</title></titleInfo><name type="conference"><namePart>Proceedings of the 5th European Conference on Optical Chemical Sensors and Biosensors, Lyon-Villeurbanne, France</namePart><namePart>EUROPT(R)ODE V S.I.</namePart><namePart type="date">20000416</namePart><namePart type="date">20000419</namePart></name><name type="personal"><namePart>Prof. P.R. Coulet and Dr. N. Jaffrezic-Renault</namePart><role><roleTerm type="text">editor</roleTerm></role></name><genre type="journal" authority="ISTEX" authorityURI="https://publication-type.data.istex.fr" valueURI="https://publication-type.data.istex.fr/ark:/67375/JMC-0GLKJH51-B">journal</genre><originInfo><publisher>ELSEVIER</publisher><dateIssued encoding="w3cdtf">20010415</dateIssued></originInfo><identifier type="ISSN">0925-4005</identifier><identifier type="PII">S0925-4005(00)X0073-1</identifier><part><date>20010415</date><detail type="issue"><title>Proceedings of the 5th European Conference on Optical Chemical Sensors and Biosensors, Lyon-Villeurbanne, France</title></detail><detail type="volume"><number>74</number><caption>vol.</caption></detail><detail type="issue"><number>1–3</number><caption>no.</caption></detail><extent unit="issue-pages"><start>1</start><end>216</end></extent><extent unit="pages"><start>186</start><end>189</end></extent></part></relatedItem><identifier type="istex">761D978B0FBD55D0ACAA8D2961609C48C8E91116</identifier><identifier type="ark">ark:/67375/6H6-MCHLVSQB-W</identifier><identifier type="DOI">10.1016/S0925-4005(00)00731-0</identifier><identifier type="PII">S0925-4005(00)00731-0</identifier><accessCondition type="use and reproduction" contentType="copyright">©2001 Elsevier Science B.V.</accessCondition><recordInfo><recordContentSource authority="ISTEX" authorityURI="https://loaded-corpus.data.istex.fr" valueURI="https://loaded-corpus.data.istex.fr/ark:/67375/XBH-HKKZVM7B-M">elsevier</recordContentSource><recordOrigin>Elsevier Science B.V., ©2001</recordOrigin></recordInfo></mods><json:item><extension>json</extension><original>false</original><mimetype>application/json</mimetype><uri>https://api.istex.fr/document/761D978B0FBD55D0ACAA8D2961609C48C8E91116/metadata/json</uri></json:item></metadata><serie></serie></istex></record>Pour manipuler ce document sous Unix (Dilib)
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