State Key Laboratory of Coordination Chemistry, Chemistry and Biomedicine Innovation Center of Nanjing University, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China.
School of Primary Education, Chongqing Normal University, Chongqing 400700, China.
Org Lett. 2021 Apr 16;23(8):2933-2937. doi: 10.1021/acs.orglett.1c00580. Epub 2021 Apr 5.
Oxazole is an important pharmacophore and exists in the backbone of many bioactive peptide natural products and peptidomimetics. Efficient methods for the synthesis and direct functionalization of complex oxazole-containing peptides are in high demand. Herein, we report the late-stage site-selective functionalization of oxazole-containing peptides via palladium-catalyzed δ-C(sp)-H olefination of phenylalanine, tryptophan, and tyrosine residues. This strategy utilizes oxazole motifs as internal directing groups and provides access to oxazole-containing peptide macrocycles with bioactivities.
恶唑是一种重要的药效团，存在于许多生物活性肽天然产物和肽模拟物的骨架中。高效的合成和直接功能化复杂含恶唑肽的方法需求很高。在此，我们报告了通过钯催化的苯丙氨酸、色氨酸和酪氨酸残基的δ-C(sp)-H 烯烃化反应，对含恶唑肽进行晚期位点选择性功能化。该策略利用恶唑基作为内部导向基团，为具有生物活性的含恶唑肽大环提供了途径。
