化学
立体选择性
生物合成
氮丙啶
立体化学
生物化学
基因
催化作用
有机化学
戒指(化学)
作者
Zhou Lu,Takayoshi Awakawa,Richiro Ushimaru,Masahiro Kanaida,Ikuro Abe
出处
期刊:Organic Letters
[American Chemical Society]
日期:2024-01-16
卷期号:26 (3): 724-727
标识
DOI:10.1021/acs.orglett.3c04185
摘要
l-Isovaline biosynthesis by TqaLFM-ti from Tolypocladium inflatum was demonstrated in vitro. The biochemical analysis of the α-ketoglutarate-dependent oxygenase TqaL-ti revealed that it produces (2S,3S)-3-ethyl-3-methylaziridine-2-carboxylic acid from l-isoleucine, thus exhibiting a stereoselectivity different from those of the reported homologues. Remarkably, a single mutation on I295 in TqaL-ti completely exchanged its stereoselectivity to produce the C-3 stereoisomer. TqaFM-ti generates d-isovaline from (2S,3R)-aziridine-2-carboxylic acid, suggesting that the stereochemistry of the TqaL product defines that of isovaline.
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