Servatius Phil, Kazmaier Uli
Organic Chemistry, Saarland University, Campus C4.2, 66123 Saarbrücken, Germany.
Beilstein J Org Chem. 2022 Feb 4;18:174-181. doi: 10.3762/bjoc.18.19. eCollection 2022.
A peptide Claisen rearrangement is used as key step to generate a tetrapeptide with a C-terminal double unsaturated side chain. Activation and cyclization give direct access to cyclopeptides related to naturally occurring histone deacetylase (HDAC) inhibitors Cyl-1 and Cyl-2. Late stage modifications on the unsaturated amino acid side chain allow the introduction of functionalities which might coordinate to metal ions in the active center of metalloproteins, such as histone deacetylases.
肽克莱森重排反应被用作关键步骤来生成具有C端双不饱和侧链的四肽。活化和环化可直接得到与天然存在的组蛋白脱乙酰酶（HDAC）抑制剂Cyl-1和Cyl-2相关的环肽。对不饱和氨基酸侧链进行后期修饰可引入可能与金属蛋白（如组蛋白脱乙酰酶）活性中心的金属离子配位的官能团。
