Department of Chemistry, Birla Institute of Technology and Science, Pilani, Rajasthan 333031, India.
Department of Chemistry and Biochemistry, Augusta University, Augusta, Georgia 30912, United States.
Org Lett. 2023 Oct 27;25(42):7673-7677. doi: 10.1021/acs.orglett.3c02994. Epub 2023 Oct 18.
Pyridyloxy-directed Rh(III)-catalyzed regioselective C3-H alkenylation of protected tyrosines was achieved with -aryl and -alkyl maleimides, furnishing a series of maleimide-appended tyrosine-based unnatural amino acids in good yields. Further, the late-stage exemplification of the strategy was successfully accomplished on tyrosine-containing dipeptides, tripeptides, and tetrapeptides in moderate reactivity. Also, the chemical applications of the strategy were successfully executed toward nailing tyrosine with other amino acids via a maleimide linker and intramolecular hydroarylation to produce tyrosine-centered stapled products and succinimide-glued macrocyclized products, respectively.
吡啶氧基导向的 Rh(III)催化的保护酪氨酸的 C3-H 区域选择性烯基化反应与 -芳基和 -烷基马来酰亚胺反应，以良好的收率得到了一系列马来酰亚胺修饰的酪氨酸衍生的非天然氨基酸。此外，该策略的后期实例研究成功地应用于含有酪氨酸的二肽、三肽和四肽中，具有中等的反应性。此外，该策略的化学应用也成功地通过马来酰亚胺键将酪氨酸与其他氨基酸连接，并通过分子内氢芳基化反应分别产生以酪氨酸为中心的订书钉产物和琥珀酰亚胺键合的大环化产物。
