4-thioribose analogues of adenosine diphosphate ribose (ADPr) peptides

Madern, J.M.; Voorneveld, J.; Rack, J.G.M.; Kistemaker, H.A.V.; Ahel, I.; Marel, G.A. van der; ... ; Filippov, D.V. (2023)

Article / Letter to editor

Adenosine diphosphate (ADP) ribosylation is an importantpost-translationalmodification (PTM) that plays a role in a wide variety of cellularprocesses. To study the enzymes responsible for the establishment,recognition, and removal of this PTM, stable analogues are invaluabletools. We describe the design and synthesis of a 4-thioribosyl APRrpeptide that has been assembled by solid phase synthesis. The key4-thioribosyl serine building block was obtained in a stereoselectiveglycosylation reaction using an alkynylbenzoate 4-thioribosyl donor.

• All authors: Madern, J.M.; Voorneveld, J.; Rack, J.G.M.; Kistemaker, H.A.V.; Ahel, I.; Marel, G.A. van der; Codee, J.D.C.; Filippov, D.V.
• Date: 2023-06-20
• Journal: Organic Letters
• Volume: 25
• Issue: 27
• Pages: 4980 - 4984
• DOI: doi:10.1021/acs.orglett.3c01554
• Link: https://pubs.acs.org/doi/10.1021/acs.orglett.3c01554