Insights into the Soluble PEG-Supported Synthesis of Cytosine-Containing Nucleoside 5′-Mono-, Di-, and Triphosphates
Nucleoside phosphoesters (nucleotides) have crucial roles in a large variety of biological processes including nucleic acid biosynthesis and their corresponding analogues are extensively used as biological tools. Herein, we describe a new and efficient synthetic procedure involving polyethylene glyc...
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| Veröffentlicht in: | Journal of organic chemistry 2009-12, Vol.74 (23), p.9165-9172 |
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| container_end_page | 9172 |
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| container_issue | 23 |
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| container_title | Journal of organic chemistry |
| container_volume | 74 |
| creator | Crauste, Céline Périgaud, Christian Peyrottes, Suzanne |
| description | Nucleoside phosphoesters (nucleotides) have crucial roles in a large variety of biological processes including nucleic acid biosynthesis and their corresponding analogues are extensively used as biological tools. Herein, we describe a new and efficient synthetic procedure involving polyethylene glycol (PEG) as soluble support and regioselective mono-, di-, and triphosphorylation steps. Applied to natural and synthetic cytosine containing nucleosides, this methodology allowed the preparation of various phosphorylated forms in high yields and good purity. |
| doi_str_mv | 10.1021/jo901931z |
| format | Article |
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Org. Chem</addtitle><description>Nucleoside phosphoesters (nucleotides) have crucial roles in a large variety of biological processes including nucleic acid biosynthesis and their corresponding analogues are extensively used as biological tools. Herein, we describe a new and efficient synthetic procedure involving polyethylene glycol (PEG) as soluble support and regioselective mono-, di-, and triphosphorylation steps. Applied to natural and synthetic cytosine containing nucleosides, this methodology allowed the preparation of various phosphorylated forms in high yields and good purity.</description><subject>Carbohydrates. Nucleosides and nucleotides</subject><subject>Chemical Sciences</subject><subject>Chemistry</subject><subject>Cytosine Nucleotides - chemical synthesis</subject><subject>Exact sciences and technology</subject><subject>Medicinal Chemistry</subject><subject>Methods</subject><subject>Nucleosides, nucleotides and oligonucleotides</subject><subject>Nucleotides - chemical synthesis</subject><subject>Organic chemistry</subject><subject>Phosphorylation</subject><subject>Polyethylene Glycols - chemistry</subject><subject>Preparations and properties</subject><subject>Solubility</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkc1u1DAQxy1ERZfCgRdAviCEVBd_5MvHailtpS0gbTlHk8RpXGXt1ONUWk48E4_Ek-Cqq90LPtjS-KffaOZPyDvBzwSX4vO911xoJX69IAuRS84KzbOXZMG5lEzJQh2T14j3PJ08z1-RY6ErnZVZtSCP1w7t3RCRWhc9jYOhaz_OzWjoj4tLtp6nyYdoOrreuvSJFqnv6XIbPVpn2NK7CNZZd0e_ze1oUrUzNP_7-w-78c6zU_rFpgtcR2-DnQaP0wDR4Bty1MOI5u3uPSE_v17cLq_Y6vvl9fJ8xSATKrKy57wTXSNE1oDJoS0KWQCUCsBkBU8TVEpDrgvTySbPVNP3QshSt3nFtek7dUI-PXsHGOsp2A2Ebe3B1lfnq_qpxqXiaRnyUST24zM7Bf8wG4z1xmJrxhGc8TPWpVJFJYWqDtY2eMRg-r1a8PopkXqfSGLf76xzszHdgdxFkIAPOwCwhbEP4FqLe05KUalM6QMHLSb_HFxa3H8a_gNfiJ9Y</recordid><startdate>20091204</startdate><enddate>20091204</enddate><creator>Crauste, Céline</creator><creator>Périgaud, Christian</creator><creator>Peyrottes, Suzanne</creator><general>American Chemical Society</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>1XC</scope><scope>VOOES</scope><orcidid>https://orcid.org/0000-0003-4631-6927</orcidid><orcidid>https://orcid.org/0000-0002-5714-8749</orcidid><orcidid>https://orcid.org/0000-0003-1705-0576</orcidid></search><sort><creationdate>20091204</creationdate><title>Insights into the Soluble PEG-Supported Synthesis of Cytosine-Containing Nucleoside 5′-Mono-, Di-, and Triphosphates</title><author>Crauste, Céline ; Périgaud, Christian ; Peyrottes, Suzanne</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a413t-7f00d1db114bae5ac6626aa73aae460748839a596ed2b543bff11279c5809efd3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Carbohydrates. 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Org. Chem</addtitle><date>2009-12-04</date><risdate>2009</risdate><volume>74</volume><issue>23</issue><spage>9165</spage><epage>9172</epage><pages>9165-9172</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>Nucleoside phosphoesters (nucleotides) have crucial roles in a large variety of biological processes including nucleic acid biosynthesis and their corresponding analogues are extensively used as biological tools. Herein, we describe a new and efficient synthetic procedure involving polyethylene glycol (PEG) as soluble support and regioselective mono-, di-, and triphosphorylation steps. 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| fulltext | fulltext |
| identifier | ISSN: 0022-3263 |
| ispartof | Journal of organic chemistry, 2009-12, Vol.74 (23), p.9165-9172 |
| issn | 0022-3263 1520-6904 |
| language | eng |
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| source | MEDLINE; ACS Publications |
| subjects | Carbohydrates. Nucleosides and nucleotides Chemical Sciences Chemistry Cytosine Nucleotides - chemical synthesis Exact sciences and technology Medicinal Chemistry Methods Nucleosides, nucleotides and oligonucleotides Nucleotides - chemical synthesis Organic chemistry Phosphorylation Polyethylene Glycols - chemistry Preparations and properties Solubility |
| title | Insights into the Soluble PEG-Supported Synthesis of Cytosine-Containing Nucleoside 5′-Mono-, Di-, and Triphosphates |
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