Hendricks Lauren, Reinhardt Clorice R, Green Tierani, Kunczynski Lily, Roberts August Jaunzarins, Miller Naomi, Rafalin Noga, Kulik Heather J, Groves John T, Austin Rachel N
Department of Chemistry, Barnard College of Columbia University, 3009 Broadway, New York, New York 10027, United States.
Department of Chemical Engineering, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.
J Am Chem Soc. 2025 Mar 19;147(11):9085-9090. doi: 10.1021/jacs.5c00386. Epub 2025 Mar 7.
Purified alkane monooxygenase (AlkB) from (FtAlkB) catalyzes the defluorination of 1-fluorooctane, producing octanal, which is partially reduced under the reaction conditions to generate 1-octanol. This reaction occurs preferentially at the monofluorinated methyl group, with only a minor amount of oxidation at the nonfluorinated end of the molecule. The dehalogenation chemistry is specific to 1-fluorooctane, as neither 1-chlorooctane or 1-bromooctane are dehalogenated to an appreciable extent. Furthermore, cells containing the structurally related AlkB (PpAlkB) along with the full set of genes required for alkane metabolism, utilize 1-fluorooctane as their sole source of carbon with growth rates comparable to those for cells grown with octane.
从 中纯化得到的烷烃单加氧酶（AlkB，FtAlkB）催化1-氟辛烷的脱氟反应，生成辛醛，辛醛在反应条件下会部分还原生成1-辛醇。该反应优先发生在单氟甲基上，分子未氟化的一端只有少量氧化反应。这种脱卤化学性质是1-氟辛烷所特有的，因为1-氯辛烷和1-溴辛烷在相当程度上都不会发生脱卤反应。此外，含有结构相关的AlkB（PpAlkB）以及烷烃代谢所需全套基因的细胞，能够利用1-氟辛烷作为唯一碳源，其生长速率与以辛烷为碳源生长的细胞相当。
