化学
烷基化
炔烃
三氟乙酸
部分
阳离子聚合
环加成
立体化学
药物化学
叠氮化物
催化作用
残留物(化学)
有机化学
作者
Jizhou Song,Takeru Torigoe,Yoichiro Kuninobu
出处
期刊:Organic Letters
[American Chemical Society]
日期:2023-05-15
卷期号:25 (20): 3708-3712
被引量:3
标识
DOI:10.1021/acs.orglett.3c01154
摘要
The decatungstate photocatalyst [W10O32]4- efficiently promoted the C(sp3)-H alkylation of the trifluoroacetic acid salt of valine methyl ester (H-Val-OMe·TFA) with electron-deficient alkenes under UV irradiation. The electrostatic interaction between the cationic ammonium group (+NH3) of the main chain and anionic [W10O32]4- played an important role in this reaction. The influence of various protected amino acids in the C(sp3)-H alkylation was investigated as the model reaction for the alkylation of Val-containing peptides. The introduction of an alkyne moiety into Val through this alkylation was successful, and successive copper-catalyzed azide-alkyne cycloaddition (CuAAC) was demonstrated. The C(sp3)-H bond of a Val residue located at the second from the N-terminus was also successfully converted. C(sp3)-H alkylation of oligopeptides containing two Val residues selectively proceeded proximally to the N-terminus.
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