Construction of Peptide-Isoquinolone Conjugates via Rh(III)-Catalyzed C-H Activation/Annulation.
Construction of Peptide-Isoquinolone Conjugates via Rh(III)-Catalyzed C-H Activation/Annulation.
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DOI：
10.1021/acs.orglett.3c00766
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发表时间：
2023-04
期刊：
影响因子：
5.2
通讯作者：
Liangliang Song;Zhenwei Lv;Yan Li;Kui Zhang;E. V. Van der Eycken;Lingchao Cai
中科院分区：
文献类型：
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作者：
Liangliang Song;Zhenwei Lv;Yan Li;Kui Zhang;E. V. Van der Eycken;Lingchao Cai
在此，我们公开了Rh（III）催化的C-H活化/成环反应，用于基于赖氨酸的肽的衍生化，原位提供不同的肽-异喹诺酮缀合物。这种方法的特点是无外消旋化条件，高原子和步骤经济性，优异的化学和位点选择性，和广泛的范围，包括基板轴承未保护的色氨酸和酪氨酸，游离丝氨酸和谷氨酰胺，和蛋氨酸残基。肽-异喹诺酮缀合物还显示出良好的荧光性质，最大发射波长高达460 nm。重要的是，初步的抗真菌活性研究表明，肽-异喹诺酮缀合物显示出对作物和森林病原真菌的潜在活性，其中含有未保护的Tyr残基的肽-异喹诺酮缀合物对B表现出更好的抗真菌活性。cinerea和C.与阳性对照相比，
Herein, we disclose a Rh(III)-catalyzed C-H activation/annulation reaction for the derivatization of Lys-based peptides, in situ affording diverse peptide-isoquinolone conjugates. This approach features racemization-free conditions, high atom- and step-economy, excellent chemo- and site-selectivity, and broad scope including substrates bearing unprotected Trp and Tyr, free Ser and Gln, and Met residues. The peptide-isoquinolone conjugates also display good fluorescent properties with maximum emission wavelengths up to 460 nm. Importantly, preliminary antifungal activity studies indicate that peptide-isoquinolone conjugates show potential activities toward crop and forest pathogenic fungi, in which the peptide-isoquinolone conjugate bearing unprotected Tyr residue exhibits much better antifungal activities toward B. cinerea Pers. and C. chrysosperma than the positive control.