Department of Discovery Chemistry, Merck & Co., Inc., West Point, Pennsylvania 19486, United States.
J Org Chem. 2020 May 1;85(9):6225-6232. doi: 10.1021/acs.joc.0c00635. Epub 2020 Apr 21.
Unnatural amino acids are key building blocks in therapeutically relevant peptides. Thus, the development of novel methods to increase the structural diversity of the unnatural amino acid pool is needed. Herein, a photoredox-mediated decarboxylative radical conjugate addition to dehydroalanine derivatives is disclosed. Mild, robust, and general conditions were identified and applied to the diastereoselective synthesis of unnatural amino acids and the late-stage derivatization of a tripeptide.
非天然氨基酸是治疗相关肽的关键结构单元。因此，需要开发新的方法来增加非天然氨基酸库的结构多样性。本文报道了一种光氧化还原介导的去氢丙氨酸衍生物的脱羧基自由基共轭加成反应。确定了温和、稳健和通用的条件，并将其应用于非天然氨基酸的立体选择性合成和三肽的后期衍生化。
