期刊
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY
卷 85, 期 2, 页码 215-222出版社
OXFORD UNIV PRESS
DOI: 10.1093/bbb/zbaa031
关键词
deuterium labeling; hinokitiol; tropolone
Hinokitiol, a compound with broad antibacterial activity, was labeled with deuterium as a traceable molecular probe for studying its dynamics in natural environments. Deuteration mainly occurred on the ring and aliphatic hydrogens, providing insights into the biodegradation pathway of hinokitiol. The experimental results suggested that deuteration on the tropolone ring was mediated by D+ while deuteration on the aliphatic group was catalyzed by Pd(II) species.
Hinokitiol has a broad antibacterial activity against bacteria and fungi. While its biosynthetic pathway has been intensively studied, its dynamics in natural environments, such as biodegradation pathway, remain unclear. In this study, the authors report a direct deuterium labeling of hinokitiol as a traceable molecular probe to serve those studies. Hinokitiol was subjected to the H-2-Pd/C-D2O conditions and deuterated hinokitiol was obtained with excellent deuteration efficiencies and in moderate yield. The H-1 and H-2 NMR spectra indicated that all ring- and aliphatic hydrogens except that on C-6 were substituted by deuterium. According to the substrate scope and computational chemistry, deuteration on tropolone ring was suggested to proceed via D+-mediated process, and which was supported by the results of the experiment with trifluoroacetic acid and Pd(TPP)(4). On the other hand, the deuteration on aliphatic group was predicted to be catalyzed by Pd(II) species.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据