Synthetic α- and β-Ser-ADP-ribosylated Peptides Reveal α-Ser-ADPr as the Native Epimer

[Image: see text] A solid-phase methodology to synthesize oligopeptides, specifically incorporating serine residues linked to ADP-ribose (ADPr), is presented. Through the synthesis of both α- and β-anomers of the phosphoribosylated Fmoc-Ser building block and their usage in our modified solid-phase...

Descripción completa

Detalles Bibliográficos
Autores principales: Voorneveld, Jim, Rack, Johannes G. M., Ahel, Ivan, Overkleeft, Herman S., van der Marel, Gijsbert A., Filippov, Dmitri V.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2018
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6038095/
https://www.ncbi.nlm.nih.gov/pubmed/29947522
http://dx.doi.org/10.1021/acs.orglett.8b01742
_version_ 1783338428002205696
author Voorneveld, Jim
Rack, Johannes G. M.
Ahel, Ivan
Overkleeft, Herman S.
van der Marel, Gijsbert A.
Filippov, Dmitri V.
author_facet Voorneveld, Jim
Rack, Johannes G. M.
Ahel, Ivan
Overkleeft, Herman S.
van der Marel, Gijsbert A.
Filippov, Dmitri V.
author_sort Voorneveld, Jim
collection PubMed
description [Image: see text] A solid-phase methodology to synthesize oligopeptides, specifically incorporating serine residues linked to ADP-ribose (ADPr), is presented. Through the synthesis of both α- and β-anomers of the phosphoribosylated Fmoc-Ser building block and their usage in our modified solid-phase peptide synthesis protocol, both α- and β-ADPr peptides from a naturally Ser-ADPr containing H2B sequence were obtained. With these, and by digestion studies using the human glycohydrolase, ARH3 (hARH3), compelling evidence is obtained that the α-Ser-ADPr linkage comprises the naturally occurring configuration.
format Online
Article
Text
id pubmed-6038095
institution National Center for Biotechnology Information
language English
publishDate 2018
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-60380952018-07-15 Synthetic α- and β-Ser-ADP-ribosylated Peptides Reveal α-Ser-ADPr as the Native Epimer Voorneveld, Jim Rack, Johannes G. M. Ahel, Ivan Overkleeft, Herman S. van der Marel, Gijsbert A. Filippov, Dmitri V. Org Lett [Image: see text] A solid-phase methodology to synthesize oligopeptides, specifically incorporating serine residues linked to ADP-ribose (ADPr), is presented. Through the synthesis of both α- and β-anomers of the phosphoribosylated Fmoc-Ser building block and their usage in our modified solid-phase peptide synthesis protocol, both α- and β-ADPr peptides from a naturally Ser-ADPr containing H2B sequence were obtained. With these, and by digestion studies using the human glycohydrolase, ARH3 (hARH3), compelling evidence is obtained that the α-Ser-ADPr linkage comprises the naturally occurring configuration. American Chemical Society 2018-06-27 2018-07-06 /pmc/articles/PMC6038095/ /pubmed/29947522 http://dx.doi.org/10.1021/acs.orglett.8b01742 Text en Copyright © 2018 American Chemical Society This is an open access article published under a Creative Commons Non-Commercial No Derivative Works (CC-BY-NC-ND) Attribution License (http://pubs.acs.org/page/policy/authorchoice_ccbyncnd_termsofuse.html) , which permits copying and redistribution of the article, and creation of adaptations, all for non-commercial purposes.
spellingShingle Voorneveld, Jim
Rack, Johannes G. M.
Ahel, Ivan
Overkleeft, Herman S.
van der Marel, Gijsbert A.
Filippov, Dmitri V.
Synthetic α- and β-Ser-ADP-ribosylated Peptides Reveal α-Ser-ADPr as the Native Epimer
title Synthetic α- and β-Ser-ADP-ribosylated Peptides Reveal α-Ser-ADPr as the Native Epimer
title_full Synthetic α- and β-Ser-ADP-ribosylated Peptides Reveal α-Ser-ADPr as the Native Epimer
title_fullStr Synthetic α- and β-Ser-ADP-ribosylated Peptides Reveal α-Ser-ADPr as the Native Epimer
title_full_unstemmed Synthetic α- and β-Ser-ADP-ribosylated Peptides Reveal α-Ser-ADPr as the Native Epimer
title_short Synthetic α- and β-Ser-ADP-ribosylated Peptides Reveal α-Ser-ADPr as the Native Epimer
title_sort synthetic α- and β-ser-adp-ribosylated peptides reveal α-ser-adpr as the native epimer
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6038095/
https://www.ncbi.nlm.nih.gov/pubmed/29947522
http://dx.doi.org/10.1021/acs.orglett.8b01742
work_keys_str_mv AT voorneveldjim syntheticaandbseradpribosylatedpeptidesrevealaseradprasthenativeepimer
AT rackjohannesgm syntheticaandbseradpribosylatedpeptidesrevealaseradprasthenativeepimer
AT ahelivan syntheticaandbseradpribosylatedpeptidesrevealaseradprasthenativeepimer
AT overkleefthermans syntheticaandbseradpribosylatedpeptidesrevealaseradprasthenativeepimer
AT vandermarelgijsberta syntheticaandbseradpribosylatedpeptidesrevealaseradprasthenativeepimer
AT filippovdmitriv syntheticaandbseradpribosylatedpeptidesrevealaseradprasthenativeepimer

Ejemplares similares