Post-synthetic modification of DNA by inverse-electron-demand Diels-Alder reaction
There is currently a tremendous interest in developing bioorthogonal “click chemistry” methods for the modification of biopolymers. Very recently, inverse-electron-demand Diels−Alder reactions have received attention, but to date they have not been applied to nucleic acids. Here we describe the firs...
Saved in:
| Main Authors: | , , |
|---|---|
| Format: | Article (Journal) |
| Language: | English |
| Published: |
June 15, 2010
|
| In: |
Journal of the American Chemical Society
Year: 2010, Volume: 132, Issue: 26, Pages: 8846-8847 |
| ISSN: | 1520-5126 |
| DOI: | 10.1021/ja102871p |
| Online Access: | Resolving-System, lizenzpflichtig, Volltext: https://doi.org/10.1021/ja102871p Verlag, lizenzpflichtig, Volltext: https://pubs.acs.org/doi/10.1021/ja102871p 
|
| Author Notes: | Juliane Schoch, Manfred Wiessler, and Andres Jäschke |
MARC
| LEADER | 00000caa a2200000 c 4500 | ||
|---|---|---|---|
| 001 | 185106303X | ||
| 003 | DE-627 | ||
| 005 | 20230710125409.0 | ||
| 007 | cr uuu---uuuuu | ||
| 008 | 230627s2010 xx |||||o 00| ||eng c | ||
| 024 | 7 | |a 10.1021/ja102871p |2 doi | |
| 035 | |a (DE-627)185106303X | ||
| 035 | |a (DE-599)KXP185106303X | ||
| 035 | |a (OCoLC)1389793895 | ||
| 040 | |a DE-627 |b ger |c DE-627 |e rda | ||
| 041 | |a eng | ||
| 084 | |a 32 |2 sdnb | ||
| 100 | 1 | |a Schoch, Juliane |e VerfasserIn |0 (DE-588)1025138104 |0 (DE-627)721236138 |0 (DE-576)369978072 |4 aut | |
| 245 | 1 | 0 | |a Post-synthetic modification of DNA by inverse-electron-demand Diels-Alder reaction |c Juliane Schoch, Manfred Wiessler, and Andres Jäschke |
| 264 | 1 | |c June 15, 2010 | |
| 300 | |a 2 | ||
| 336 | |a Text |b txt |2 rdacontent | ||
| 337 | |a Computermedien |b c |2 rdamedia | ||
| 338 | |a Online-Ressource |b cr |2 rdacarrier | ||
| 500 | |a Gesehen am 27.06.2023 | ||
| 520 | |a There is currently a tremendous interest in developing bioorthogonal “click chemistry” methods for the modification of biopolymers. Very recently, inverse-electron-demand Diels−Alder reactions have received attention, but to date they have not been applied to nucleic acids. Here we describe the first example of DNA modification by inverse-electron-demand Diels-Alder reaction. We synthesized four different building blocks for 3′-terminal, 5′-terminal, and internal incorporation of norbornene dienophiles into oligonucleotides. These DNA strands were either directly reacted with suitably derivatized tetrazine dienes or first subjected to enzymatic manipulations. We demonstrate that the inverse-electron-demand Diels−Alder reaction allows efficient site-specific post-synthetic conjugation, often at a 1:1 stoichiometry, without any side reaction. The reaction works in aqueous media at room temperature, and no transition metals are required. Both short chemically synthesized oligonucleotides and long enzymatically amplified DNA strands were successfully conjugated. | ||
| 700 | 1 | |a Wießler, Manfred |e VerfasserIn |0 (DE-588)117668387X |0 (DE-627)1047653249 |0 (DE-576)51675419X |4 aut | |
| 700 | 1 | |a Jäschke, Andres |d 1962- |e VerfasserIn |0 (DE-588)1025112261 |0 (DE-627)751682756 |0 (DE-576)170797481 |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |a American Chemical Society |t Journal of the American Chemical Society |d Washington, DC : ACS Publications, 1879 |g 132(2010), 26, Seite 8846-8847 |w (DE-627)268132836 |w (DE-600)1472210-0 |w (DE-576)090854284 |x 1520-5126 |7 nnas |
| 773 | 1 | 8 | |g volume:132 |g year:2010 |g number:26 |g pages:8846-8847 |g extent:2 |a Post-synthetic modification of DNA by inverse-electron-demand Diels-Alder reaction |
| 856 | 4 | 0 | |u https://doi.org/10.1021/ja102871p |x Resolving-System |x Verlag |z lizenzpflichtig |3 Volltext |
| 856 | 4 | 0 | |u https://pubs.acs.org/doi/10.1021/ja102871p |x Verlag |z lizenzpflichtig |3 Volltext |
| 951 | |a AR | ||
| 992 | |a 20230627 | ||
| 993 | |a Article | ||
| 994 | |a 2010 | ||
| 998 | |g 1025112261 |a Jäschke, Andres |m 1025112261:Jäschke, Andres |d 160000 |d 160100 |e 160000PJ1025112261 |e 160100PJ1025112261 |k 0/160000/ |k 1/160000/160100/ |p 3 |y j | ||
| 998 | |g 117668387X |a Wießler, Manfred |m 117668387X:Wießler, Manfred |d 50000 |e 50000PW117668387X |k 0/50000/ |p 2 | ||
| 998 | |g 1025138104 |a Schoch, Juliane |m 1025138104:Schoch, Juliane |d 160000 |d 160100 |e 160000PS1025138104 |e 160100PS1025138104 |k 0/160000/ |k 1/160000/160100/ |p 1 |x j | ||
| 999 | |a KXP-PPN185106303X |e 4343887081 | ||
| BIB | |a Y | ||
| SER | |a journal | ||
| JSO | |a {"name":{"displayForm":["Juliane Schoch, Manfred Wiessler, and Andres Jäschke"]},"origin":[{"dateIssuedKey":"2010","dateIssuedDisp":"June 15, 2010"}],"id":{"eki":["185106303X"],"doi":["10.1021/ja102871p"]},"physDesc":[{"extent":"2 S."}],"relHost":[{"name":{"displayForm":["Ed.: Allen J. Bard [u.a.]"]},"id":{"issn":["1520-5126"],"zdb":["1472210-0"],"eki":["268132836"]},"origin":[{"publisher":"ACS Publications ; American Chemical Society","dateIssuedKey":"1879","dateIssuedDisp":"1879-","publisherPlace":"Washington, DC ; Washington, DC"}],"recId":"268132836","language":["eng"],"corporate":[{"roleDisplay":"VerfasserIn","display":"American Chemical Society","role":"aut"}],"type":{"media":"Online-Ressource","bibl":"periodical"},"disp":"American Chemical SocietyJournal of the American Chemical Society","note":["Gesehen am 25.08.2020"],"titleAlt":[{"title":"JACS"},{"title":"web edition"}],"part":{"extent":"2","text":"132(2010), 26, Seite 8846-8847","volume":"132","issue":"26","pages":"8846-8847","year":"2010"},"pubHistory":["1.1879 -"],"title":[{"title_sort":"Journal of the American Chemical Society","title":"Journal of the American Chemical Society","subtitle":"JACS"}]}],"person":[{"given":"Juliane","family":"Schoch","role":"aut","display":"Schoch, Juliane","roleDisplay":"VerfasserIn"},{"given":"Manfred","family":"Wießler","role":"aut","display":"Wießler, Manfred","roleDisplay":"VerfasserIn"},{"display":"Jäschke, Andres","roleDisplay":"VerfasserIn","role":"aut","family":"Jäschke","given":"Andres"}],"title":[{"title_sort":"Post-synthetic modification of DNA by inverse-electron-demand Diels-Alder reaction","title":"Post-synthetic modification of DNA by inverse-electron-demand Diels-Alder reaction"}],"note":["Gesehen am 27.06.2023"],"type":{"bibl":"article-journal","media":"Online-Ressource"},"language":["eng"],"recId":"185106303X"} | ||
| SRT | |a SCHOCHJULIPOSTSYNTHE1520 | ||