Peroxide-Mediated Release of Organophosphates from Boron-Containing Phosphotriesters: A New Class of Organophosphate Prodrugs

[Image: see text] Phosphate mono- and diesters can be liberated efficiently from boryl allyloxy (BAO) and related phosphotriesters by H(2)O(2). This protocol was applied to the release of a phosphorylated serine derivative and the nucleotide analogue AZT monophosphate. Nucleotide release in the pres...

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Autores principales: Klootwyk, Brittany M., Ryan, Amy E., Lopez, Arbil, McCloskey, Mitchell J. R., Janosko, Chasity P., Deiters, Alexander, Floreancig, Paul E.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10391626/
https://www.ncbi.nlm.nih.gov/pubmed/37463277
http://dx.doi.org/10.1021/acs.orglett.3c02036
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author Klootwyk, Brittany M.
Ryan, Amy E.
Lopez, Arbil
McCloskey, Mitchell J. R.
Janosko, Chasity P.
Deiters, Alexander
Floreancig, Paul E.
author_facet Klootwyk, Brittany M.
Ryan, Amy E.
Lopez, Arbil
McCloskey, Mitchell J. R.
Janosko, Chasity P.
Deiters, Alexander
Floreancig, Paul E.
author_sort Klootwyk, Brittany M.
collection PubMed
description [Image: see text] Phosphate mono- and diesters can be liberated efficiently from boryl allyloxy (BAO) and related phosphotriesters by H(2)O(2). This protocol was applied to the release of a phosphorylated serine derivative and the nucleotide analogue AZT monophosphate. Nucleotide release in the presence of ATP and a kinase provides a diphosphate, demonstrating that this method can be applied to biological processes.
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spelling pubmed-103916262023-08-02 Peroxide-Mediated Release of Organophosphates from Boron-Containing Phosphotriesters: A New Class of Organophosphate Prodrugs Klootwyk, Brittany M. Ryan, Amy E. Lopez, Arbil McCloskey, Mitchell J. R. Janosko, Chasity P. Deiters, Alexander Floreancig, Paul E. Org Lett [Image: see text] Phosphate mono- and diesters can be liberated efficiently from boryl allyloxy (BAO) and related phosphotriesters by H(2)O(2). This protocol was applied to the release of a phosphorylated serine derivative and the nucleotide analogue AZT monophosphate. Nucleotide release in the presence of ATP and a kinase provides a diphosphate, demonstrating that this method can be applied to biological processes. American Chemical Society 2023-07-18 /pmc/articles/PMC10391626/ /pubmed/37463277 http://dx.doi.org/10.1021/acs.orglett.3c02036 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 Klootwyk, Brittany M.
Ryan, Amy E.
Lopez, Arbil
McCloskey, Mitchell J. R.
Janosko, Chasity P.
Deiters, Alexander
Floreancig, Paul E.
Peroxide-Mediated Release of Organophosphates from Boron-Containing Phosphotriesters: A New Class of Organophosphate Prodrugs
title Peroxide-Mediated Release of Organophosphates from Boron-Containing Phosphotriesters: A New Class of Organophosphate Prodrugs
title_full Peroxide-Mediated Release of Organophosphates from Boron-Containing Phosphotriesters: A New Class of Organophosphate Prodrugs
title_fullStr Peroxide-Mediated Release of Organophosphates from Boron-Containing Phosphotriesters: A New Class of Organophosphate Prodrugs
title_full_unstemmed Peroxide-Mediated Release of Organophosphates from Boron-Containing Phosphotriesters: A New Class of Organophosphate Prodrugs
title_short Peroxide-Mediated Release of Organophosphates from Boron-Containing Phosphotriesters: A New Class of Organophosphate Prodrugs
title_sort peroxide-mediated release of organophosphates from boron-containing phosphotriesters: a new class of organophosphate prodrugs
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10391626/
https://www.ncbi.nlm.nih.gov/pubmed/37463277
http://dx.doi.org/10.1021/acs.orglett.3c02036
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