4-Thioribose Analogues of Adenosine Diphosphate Ribose (ADPr) Peptides

[Image: see text] Adenosine diphosphate (ADP) ribosylation is an important post-translational modification (PTM) that plays a role in a wide variety of cellular processes. To study the enzymes responsible for the establishment, recognition, and removal of this PTM, stable analogues are invaluable to...

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Autores principales: Madern, Jerre M., Voorneveld, Jim, Rack, Johannes G. M., Kistemaker, Hans A. V., Ahel, Ivan, van der Marel, Gijsbert A., Codée, Jeroen D. C., Filippov, Dmitri V.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10353035/
https://www.ncbi.nlm.nih.gov/pubmed/37338412
http://dx.doi.org/10.1021/acs.orglett.3c01554
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author Madern, Jerre M.
Voorneveld, Jim
Rack, Johannes G. M.
Kistemaker, Hans A. V.
Ahel, Ivan
van der Marel, Gijsbert A.
Codée, Jeroen D. C.
Filippov, Dmitri V.
author_facet Madern, Jerre M.
Voorneveld, Jim
Rack, Johannes G. M.
Kistemaker, Hans A. V.
Ahel, Ivan
van der Marel, Gijsbert A.
Codée, Jeroen D. C.
Filippov, Dmitri V.
author_sort Madern, Jerre M.
collection PubMed
description [Image: see text] Adenosine diphosphate (ADP) ribosylation is an important post-translational modification (PTM) that plays a role in a wide variety of cellular processes. To study the enzymes responsible for the establishment, recognition, and removal of this PTM, stable analogues are invaluable tools. We describe the design and synthesis of a 4-thioribosyl APRr peptide that has been assembled by solid phase synthesis. The key 4-thioribosyl serine building block was obtained in a stereoselective glycosylation reaction using an alkynylbenzoate 4-thioribosyl donor.
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spelling pubmed-103530352023-07-19 4-Thioribose Analogues of Adenosine Diphosphate Ribose (ADPr) Peptides Madern, Jerre M. Voorneveld, Jim Rack, Johannes G. M. Kistemaker, Hans A. V. Ahel, Ivan van der Marel, Gijsbert A. Codée, Jeroen D. C. Filippov, Dmitri V. Org Lett [Image: see text] Adenosine diphosphate (ADP) ribosylation is an important post-translational modification (PTM) that plays a role in a wide variety of cellular processes. To study the enzymes responsible for the establishment, recognition, and removal of this PTM, stable analogues are invaluable tools. We describe the design and synthesis of a 4-thioribosyl APRr peptide that has been assembled by solid phase synthesis. The key 4-thioribosyl serine building block was obtained in a stereoselective glycosylation reaction using an alkynylbenzoate 4-thioribosyl donor. American Chemical Society 2023-06-20 /pmc/articles/PMC10353035/ /pubmed/37338412 http://dx.doi.org/10.1021/acs.orglett.3c01554 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Madern, Jerre M.
Voorneveld, Jim
Rack, Johannes G. M.
Kistemaker, Hans A. V.
Ahel, Ivan
van der Marel, Gijsbert A.
Codée, Jeroen D. C.
Filippov, Dmitri V.
4-Thioribose Analogues of Adenosine Diphosphate Ribose (ADPr) Peptides
title 4-Thioribose Analogues of Adenosine Diphosphate Ribose (ADPr) Peptides
title_full 4-Thioribose Analogues of Adenosine Diphosphate Ribose (ADPr) Peptides
title_fullStr 4-Thioribose Analogues of Adenosine Diphosphate Ribose (ADPr) Peptides
title_full_unstemmed 4-Thioribose Analogues of Adenosine Diphosphate Ribose (ADPr) Peptides
title_short 4-Thioribose Analogues of Adenosine Diphosphate Ribose (ADPr) Peptides
title_sort 4-thioribose analogues of adenosine diphosphate ribose (adpr) peptides
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10353035/
https://www.ncbi.nlm.nih.gov/pubmed/37338412
http://dx.doi.org/10.1021/acs.orglett.3c01554
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