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


ABSTRACT: 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.

SUBMITTER: Madern JM 

PROVIDER: S-EPMC10353035 | biostudies-literature | 2023 Jul

REPOSITORIES: biostudies-literature

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

Madern Jerre M JM   Voorneveld Jim J   Rack Johannes G M JGM   Kistemaker Hans A V HAV   Ahel Ivan I   van der Marel Gijsbert A GA   Codée Jeroen D C JDC   Filippov Dmitri V DV  

Organic letters 20230620 27


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 re  ...[more]

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