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

Author(s):
Madern, J.M.; Voorneveld, J. (0000-0002-1046-6926); Rack, J.G.M.; Kistemaker, H.A.V.; Ahel, I.; Marel, G.A. van der (0000-0001-8917-3458); Codee, J.D.C. (0000-0003-3531-2138); Filippov, D.V. (0000-0002-6978-7425)
Published
2023
Publication type
Article / Letter to editor

Abstract

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.

Date issued
2023-06-20
Language
English
Publisher
AMER CHEMICAL SOC
Is part of
Organic Letters (2023), Vol. 25, no. 27, p. 4980-4984
hdl
1887/3656606
doi
10.1021/acs.orglett.3c01554
URL
https://pubs.acs.org/doi/10.1021/acs.orglett.3c01554