Leiden Institute of Chemistry, Leiden University, Einsteinweg 55, 2333 CC Leiden, The Netherlands.
Sir William Dunn School of Pathology, University of Oxford, South Parks Road, Oxford OX1 3RE, United Kingdom.
Org Lett. 2023 Jul 14;25(27):4980-4984. doi: 10.1021/acs.orglett.3c01554. Epub 2023 Jun 20.
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.
二磷酸腺苷（ADP）核糖基化是一种重要的翻译后修饰（PTM），在多种细胞过程中发挥作用。为了研究建立、识别和去除这种 PTM 的酶，稳定类似物是非常有价值的工具。我们描述了通过固相合成组装的 4-硫代核糖基 APRr 肽的设计和合成。关键的 4-硫代核糖基丝氨酸砌块是通过使用炔基苯甲酸酯 4-硫代核糖基供体的立体选择性糖苷化反应获得的。
