Mimetics of ADP-Ribosylated Histidine through Copper(I)-Catalyzed Click Chemistry

[Image: see text] A convergent synthesis provided nearly perfect τ-ADP-ribosylated histidine isosteres (His*-τ-ADPr) via a copper(I)-catalyzed cycloaddition between an azido-ADP-ribosyl analogue and an oligopeptide carrying a propargyl glycine. Both α- and β-configured azido-ADP-ribosyl analogues ha...

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Autores principales: Minnee, Hugo, Rack, Johannes G. M., van der Marel, Gijsbert A., Overkleeft, Herman S., Codée, Jeroen D. C., Ahel, Ivan, Filippov, Dmitri V.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9171823/
https://www.ncbi.nlm.nih.gov/pubmed/35587229
http://dx.doi.org/10.1021/acs.orglett.2c01300
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author Minnee, Hugo
Rack, Johannes G. M.
van der Marel, Gijsbert A.
Overkleeft, Herman S.
Codée, Jeroen D. C.
Ahel, Ivan
Filippov, Dmitri V.
author_facet Minnee, Hugo
Rack, Johannes G. M.
van der Marel, Gijsbert A.
Overkleeft, Herman S.
Codée, Jeroen D. C.
Ahel, Ivan
Filippov, Dmitri V.
author_sort Minnee, Hugo
collection PubMed
description [Image: see text] A convergent synthesis provided nearly perfect τ-ADP-ribosylated histidine isosteres (His*-τ-ADPr) via a copper(I)-catalyzed cycloaddition between an azido-ADP-ribosyl analogue and an oligopeptide carrying a propargyl glycine. Both α- and β-configured azido-ADP-ribosyl analogues have been synthesized. The former required participation of the C-2 ester functionality during glycosylation, while the latter was obtained in high stereoselectivity from an imidate donor with a nonparticipating para-methoxy benzyl ether. Four His*-τ-ADPr peptides were screened against a library of human ADP-ribosyl hydrolases.
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spelling pubmed-91718232022-06-08 Mimetics of ADP-Ribosylated Histidine through Copper(I)-Catalyzed Click Chemistry Minnee, Hugo Rack, Johannes G. M. van der Marel, Gijsbert A. Overkleeft, Herman S. Codée, Jeroen D. C. Ahel, Ivan Filippov, Dmitri V. Org Lett [Image: see text] A convergent synthesis provided nearly perfect τ-ADP-ribosylated histidine isosteres (His*-τ-ADPr) via a copper(I)-catalyzed cycloaddition between an azido-ADP-ribosyl analogue and an oligopeptide carrying a propargyl glycine. Both α- and β-configured azido-ADP-ribosyl analogues have been synthesized. The former required participation of the C-2 ester functionality during glycosylation, while the latter was obtained in high stereoselectivity from an imidate donor with a nonparticipating para-methoxy benzyl ether. Four His*-τ-ADPr peptides were screened against a library of human ADP-ribosyl hydrolases. American Chemical Society 2022-05-19 2022-06-03 /pmc/articles/PMC9171823/ /pubmed/35587229 http://dx.doi.org/10.1021/acs.orglett.2c01300 Text en © 2022 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 Minnee, Hugo
Rack, Johannes G. M.
van der Marel, Gijsbert A.
Overkleeft, Herman S.
Codée, Jeroen D. C.
Ahel, Ivan
Filippov, Dmitri V.
Mimetics of ADP-Ribosylated Histidine through Copper(I)-Catalyzed Click Chemistry
title Mimetics of ADP-Ribosylated Histidine through Copper(I)-Catalyzed Click Chemistry
title_full Mimetics of ADP-Ribosylated Histidine through Copper(I)-Catalyzed Click Chemistry
title_fullStr Mimetics of ADP-Ribosylated Histidine through Copper(I)-Catalyzed Click Chemistry
title_full_unstemmed Mimetics of ADP-Ribosylated Histidine through Copper(I)-Catalyzed Click Chemistry
title_short Mimetics of ADP-Ribosylated Histidine through Copper(I)-Catalyzed Click Chemistry
title_sort mimetics of adp-ribosylated histidine through copper(i)-catalyzed click chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9171823/
https://www.ncbi.nlm.nih.gov/pubmed/35587229
http://dx.doi.org/10.1021/acs.orglett.2c01300
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