Spin‐Labeled Riboswitch Synthesized from a Protected TPA Phosphoramidite Building Block

The nitroxide TPA (2,2,5,5‐tetramethyl‐pyrrolin‐1‐oxyl‐3‐acetylene) is an excellent spin label for EPR studies of RNA. Previous synthetic methods, however, are complicated and require special equipment. Herein, we describe a uridine derived phosphoramidite with a photocaged TPA unit attached. The li...

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Detalles Bibliográficos
Autores principales: Kaiser, Frank, Endeward, Burkhard, Collauto, Alberto, Scheffer, Ute, Prisner, Thomas F., Göbel, Michael W.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Research Articles
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9804336/
https://www.ncbi.nlm.nih.gov/pubmed/35903916
http://dx.doi.org/10.1002/chem.202201822
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author Kaiser, Frank
Endeward, Burkhard
Collauto, Alberto
Scheffer, Ute
Prisner, Thomas F.
Göbel, Michael W.
author_facet Kaiser, Frank
Endeward, Burkhard
Collauto, Alberto
Scheffer, Ute
Prisner, Thomas F.
Göbel, Michael W.
author_sort Kaiser, Frank
collection PubMed
description The nitroxide TPA (2,2,5,5‐tetramethyl‐pyrrolin‐1‐oxyl‐3‐acetylene) is an excellent spin label for EPR studies of RNA. Previous synthetic methods, however, are complicated and require special equipment. Herein, we describe a uridine derived phosphoramidite with a photocaged TPA unit attached. The light sensitive 2‐nitrobenzyloxymethyl group can be removed in high yield by short irradiation at 365 nm. Based on this approach, a doubly spin‐labeled 27mer neomycin sensing riboswitch was synthesized and studied by PELDOR. The overall thermal stability of the fold is not much reduced by TPA. In‐line probing nevertheless detected changes in local mobility.
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spelling pubmed-98043362023-01-03 Spin‐Labeled Riboswitch Synthesized from a Protected TPA Phosphoramidite Building Block Kaiser, Frank Endeward, Burkhard Collauto, Alberto Scheffer, Ute Prisner, Thomas F. Göbel, Michael W. Chemistry Research Articles The nitroxide TPA (2,2,5,5‐tetramethyl‐pyrrolin‐1‐oxyl‐3‐acetylene) is an excellent spin label for EPR studies of RNA. Previous synthetic methods, however, are complicated and require special equipment. Herein, we describe a uridine derived phosphoramidite with a photocaged TPA unit attached. The light sensitive 2‐nitrobenzyloxymethyl group can be removed in high yield by short irradiation at 365 nm. Based on this approach, a doubly spin‐labeled 27mer neomycin sensing riboswitch was synthesized and studied by PELDOR. The overall thermal stability of the fold is not much reduced by TPA. In‐line probing nevertheless detected changes in local mobility. John Wiley and Sons Inc. 2022-08-18 2022-10-07 /pmc/articles/PMC9804336/ /pubmed/35903916 http://dx.doi.org/10.1002/chem.202201822 Text en © 2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Research Articles
Kaiser, Frank
Endeward, Burkhard
Collauto, Alberto
Scheffer, Ute
Prisner, Thomas F.
Göbel, Michael W.
Spin‐Labeled Riboswitch Synthesized from a Protected TPA Phosphoramidite Building Block
title Spin‐Labeled Riboswitch Synthesized from a Protected TPA Phosphoramidite Building Block
title_full Spin‐Labeled Riboswitch Synthesized from a Protected TPA Phosphoramidite Building Block
title_fullStr Spin‐Labeled Riboswitch Synthesized from a Protected TPA Phosphoramidite Building Block
title_full_unstemmed Spin‐Labeled Riboswitch Synthesized from a Protected TPA Phosphoramidite Building Block
title_short Spin‐Labeled Riboswitch Synthesized from a Protected TPA Phosphoramidite Building Block
title_sort spin‐labeled riboswitch synthesized from a protected tpa phosphoramidite building block
topic Research Articles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9804336/
https://www.ncbi.nlm.nih.gov/pubmed/35903916
http://dx.doi.org/10.1002/chem.202201822
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