Fluorescent labeling of Taqman oligonucleotide probes via Cu(I)-catalyzed alkyne-azide cycloaddition (CuAAC) click chemistry
We describe an approach to the synthesis of TaqMan oligonucleotide probes that is based on Cu(I)-catalyzed alkyne-azide cycloaddition (CuAAC) click chemistry when oligonucleotides containing an internal alkynyl group at the pyrimidine position are labeled post-synthetically with a f luorescent azide...
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| Veröffentlicht in: | Russian journal of bioorganic chemistry 2017, Vol.43 (1), p.43-49 |
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| container_title | Russian journal of bioorganic chemistry |
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| creator | Vasilyeva, S. V. Burakova, E. A. Zhdanova, L. G. Anisimenko, M. S. Stetsenko, D. A. |
| description | We describe an approach to the synthesis of TaqMan oligonucleotide probes that is based on Cu(I)-catalyzed alkyne-azide cycloaddition (CuAAC) click chemistry when oligonucleotides containing an internal alkynyl group at the pyrimidine position are labeled post-synthetically with a f luorescent azide. TaqMan probes were constructed with f luorescein in different internal positions and a BHQ1 quencher on the 3′-end. Our previously designed alkynylated deoxyuridine or deoxycytidine phosphoramidites have been employed for the synthesis of alkynyl oligonucleotides. It was demonstrated that the synthesized TaqMan probes can detect accumulation of PCR product in real-time. The closer to the label the 3′-terminal quencher, the higher the quenching efficiency, but the efficiency of probe hybridization to DNA template is reduced in this case. |
| doi_str_mv | 10.1134/S1068162017010113 |
| format | Article |
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Our previously designed alkynylated deoxyuridine or deoxycytidine phosphoramidites have been employed for the synthesis of alkynyl oligonucleotides. It was demonstrated that the synthesized TaqMan probes can detect accumulation of PCR product in real-time. The closer to the label the 3′-terminal quencher, the higher the quenching efficiency, but the efficiency of probe hybridization to DNA template is reduced in this case.</description><subject>Alkynes</subject><subject>Biochemistry</subject><subject>Biomedical and Life Sciences</subject><subject>Biomedicine</subject><subject>Bioorganic Chemistry</subject><subject>Chemical synthesis</subject><subject>Cycloaddition</subject><subject>Fluorescence</subject><subject>Labels</subject><subject>Life Sciences</subject><subject>Oligonucleotides</subject><subject>Organic Chemistry</subject><subject>Real time</subject><issn>1068-1620</issn><issn>1608-330X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNp1kE9LAzEQxYMoWKsfwFvAix5W82d3kz2WxWqh4MEK3pZsNlvTpkmb7Apb_PCm1IMgnmaY93szwwPgGqN7jGn68IpRznFOEGYIozg6ASOcI55Qit5PYx_l5KCfg4sQVihCKOMj8DU1vfMqSGU7aEStjLZL6Fq4ELuNsNAZvXS2l0a5TjcKbr2rVYCfWsCyv53dJVJ0wgx71UBh1oNVidgfODlI40TT6E47C2_LfjIp76A0Wq6h_FAbHTo_XIKzVpigrn7qGLxNHxflczJ_eZqVk3kiCcU0adK8YBmrc163FLMWFS0tSEFIxpkikmZpLliT8SKjaVGgvM4aRAQmaZsyJJSiY3Bz3Bu_3_UqdNXK9d7GkxXmHDFGEMORwkdKeheCV2219Xoj_FBhVB1Crv6EHD3k6AmRtUvlf23-1_QNfp59PA</recordid><startdate>2017</startdate><enddate>2017</enddate><creator>Vasilyeva, S. 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A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Fluorescent labeling of Taqman oligonucleotide probes via Cu(I)-catalyzed alkyne-azide cycloaddition (CuAAC) click chemistry</atitle><jtitle>Russian journal of bioorganic chemistry</jtitle><stitle>Russ J Bioorg Chem</stitle><date>2017</date><risdate>2017</risdate><volume>43</volume><issue>1</issue><spage>43</spage><epage>49</epage><pages>43-49</pages><issn>1068-1620</issn><eissn>1608-330X</eissn><abstract>We describe an approach to the synthesis of TaqMan oligonucleotide probes that is based on Cu(I)-catalyzed alkyne-azide cycloaddition (CuAAC) click chemistry when oligonucleotides containing an internal alkynyl group at the pyrimidine position are labeled post-synthetically with a f luorescent azide. TaqMan probes were constructed with f luorescein in different internal positions and a BHQ1 quencher on the 3′-end. Our previously designed alkynylated deoxyuridine or deoxycytidine phosphoramidites have been employed for the synthesis of alkynyl oligonucleotides. It was demonstrated that the synthesized TaqMan probes can detect accumulation of PCR product in real-time. The closer to the label the 3′-terminal quencher, the higher the quenching efficiency, but the efficiency of probe hybridization to DNA template is reduced in this case.</abstract><cop>Moscow</cop><pub>Pleiades Publishing</pub><doi>10.1134/S1068162017010113</doi><tpages>7</tpages></addata></record> |
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| language | eng |
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| subjects | Alkynes Biochemistry Biomedical and Life Sciences Biomedicine Bioorganic Chemistry Chemical synthesis Cycloaddition Fluorescence Labels Life Sciences Oligonucleotides Organic Chemistry Real time |
| title | Fluorescent labeling of Taqman oligonucleotide probes via Cu(I)-catalyzed alkyne-azide cycloaddition (CuAAC) click chemistry |
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