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

Adenosine Diphosphate Ribose / metabolism ADP-Ribosylation Protein Processing, Post-Translational Peptides Glycosylation Adenosine Diphosphate

Journal

Organic letters
ISSN: 1523-7052
Titre abrégé: Org Lett
Pays: United States
ID NLM: 100890393

Informations de publication

Date de publication:
14 07 2023
Historique:
medline: 17 7 2023
pubmed: 20 6 2023
entrez: 20 6 2023
Statut: ppublish

Résumé

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.

Identifiants

DOI: 10.1021/acs.orglett.3c01554 PMID: 37338412 PMC: PMC10353035
pubmed: 37338412
doi: 10.1021/acs.orglett.3c01554
pmc: PMC10353035
doi:

Substances chimiques

Adenosine Diphosphate Ribose 20762-30-5
Peptides 0
Adenosine Diphosphate 61D2G4IYVH

Types de publication

Journal Article Research Support, Non-U.S. Gov't

Langues

eng

Sous-ensembles de citation

IM

Pagination

4980-4984

Subventions

Organisme : Wellcome Trust
Pays : United Kingdom
Organisme : Wellcome Trust
ID : 210634
Pays : United Kingdom

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Auteurs

Jerre M Madern (JM)

Leiden Institute of Chemistry, Leiden University, Einsteinweg 55, 2333 CC Leiden, The Netherlands.

Jim Voorneveld (J)

Leiden Institute of Chemistry, Leiden University, Einsteinweg 55, 2333 CC Leiden, The Netherlands.

Johannes G M Rack (JGM)

Sir William Dunn School of Pathology, University of Oxford, South Parks Road, Oxford OX1 3RE, United Kingdom.

Hans A V Kistemaker (HAV)

Leiden Institute of Chemistry, Leiden University, Einsteinweg 55, 2333 CC Leiden, The Netherlands.

Ivan Ahel (I)

Sir William Dunn School of Pathology, University of Oxford, South Parks Road, Oxford OX1 3RE, United Kingdom.

Gijsbert A van der Marel (GA)

Leiden Institute of Chemistry, Leiden University, Einsteinweg 55, 2333 CC Leiden, The Netherlands.

Jeroen D C Codée (JDC)

Leiden Institute of Chemistry, Leiden University, Einsteinweg 55, 2333 CC Leiden, The Netherlands.
ORCID: 0000-0003-3531-2138

Dmitri V Filippov (DV)

Leiden Institute of Chemistry, Leiden University, Einsteinweg 55, 2333 CC Leiden, The Netherlands.
ORCID: 0000-0002-6978-7425

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Classifications MeSH

questionsmedicales.fr › Acides nucléiques, nucléotides et nucléosides › Nucléotides › Ribonucléotides › Nucléoside diphosphate ose › Adénosine diphosphate ose › Adénosine diphosphate ribose › 4-Thioribose Analogues of Adenosine...
questionsmedicales.fr › Phénomènes génétiques › Régulation de l'expression des gènes › Modification traductionnelle des protéines › Maturation post-traductionnelle des protéines › ADP-Ribosylation › 4-Thioribose Analogues of Adenosine...
questionsmedicales.fr › Phénomènes génétiques › Régulation de l'expression des gènes › Modification traductionnelle des protéines › Maturation post-traductionnelle des protéines › 4-Thioribose Analogues of Adenosine...
questionsmedicales.fr › Acides aminés, peptides et protéines › Peptides › 4-Thioribose Analogues of Adenosine...
questionsmedicales.fr › Métabolisme › Métabolisme glucidique › Glycosylation › 4-Thioribose Analogues of Adenosine...
questionsmedicales.fr › Acides nucléiques, nucléotides et nucléosides › Nucléotides › Ribonucléotides › Nucléotides adényliques › ADP › 4-Thioribose Analogues of Adenosine...