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
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<front><div type="abstract" xml: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.</div>
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<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>
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<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>
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<mods version="3.6"><titleInfo lang="en"><title>Photolabile group for 5′-OH protection of nucleosides: synthesis and photodeprotection rate</title>
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<titleInfo type="alternative" lang="en" contentType="CDATA"><title>Photolabile group for 5′-OH protection of nucleosides: synthesis and photodeprotection rate</title>
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<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>
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<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>
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<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>
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<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>
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<titleInfo type="abbreviated"><title>SNB</title>
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<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>
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<name type="personal"><namePart>Prof. P.R. Coulet and Dr. N. Jaffrezic-Renault</namePart>
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<dateIssued encoding="w3cdtf">20010415</dateIssued>
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<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>
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<detail type="volume"><number>74</number>
<caption>vol.</caption>
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<detail type="issue"><number>1–3</number>
<caption>no.</caption>
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<extent unit="issue-pages"><start>1</start>
<end>216</end>
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<extent unit="pages"><start>186</start>
<end>189</end>
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<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>
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