Ma Long, Bartholome Axel, Tong Ming Him, Qin Zhiwei, Yu Yi, Shepherd Thomas, Kyeremeh Kwaku, Deng Hai, O'Hagan David
EaStChem School of Chemistry , University of St Andrews , North Haugh , St Andrews KY169ST , UK . Email:
Marine Biodiscovery Centre , Department of Chemistry , University of Aberdeen , Meston Walk , Aberdeen AB24 3UE , UK . Email:
Chem Sci. 2015 Feb 1;6(2):1414-1419. doi: 10.1039/c4sc03540b. Epub 2014 Dec 3.
(234)-5-Fluoro-2,3,4-trihydroxypentanoic acid (5-FHPA) has been discovered as a new fluorometabolite in the soil bacterium sp. MA37. Exogenous addition of 5-fluoro-5-deoxy-d-ribose (5-FDR) into the cell free extract of MA37 demonstrated that 5-FDR was an intermediate to a range of unidentified fluorometabolites, distinct from fluoroacetate (FAc) and 4-fluorothreonine (4-FT). Bioinformatics analysis allowed identification of a gene cluster (), encoding a pathway to the biosynthesis of 5-FHPA. Over-expression and assay of FdrC indicated that FdrC is a NAD dependent dehydrogenase responsible for oxidation of 5-FDR into 5-fluoro-5-deoxy-lactone, followed by hydrolysis to 5-FHPA. The identity of 5-FHPA in the fermentation broth was confirmed by synthesis of a reference compound and then co-correlation by F-NMR and GC-MS analysis. The occurrence of 5-FHPA proves the existence of a new fluorometabolite pathway.
（234）-5-氟-2,3,4-三羟基戊酸（5-FHPA）已被发现是土壤细菌sp. MA37中的一种新的氟代谢产物。向MA37的无细胞提取物中外源添加5-氟-5-脱氧-D-核糖（5-FDR）表明，5-FDR是一系列未鉴定的氟代谢产物的中间体，与氟乙酸（FAc）和4-氟苏氨酸（4-FT）不同。生物信息学分析有助于鉴定一个基因簇（），该基因簇编码5-FHPA生物合成途径。FdrC的过表达和测定表明，FdrC是一种NAD依赖性脱氢酶，负责将5-FDR氧化为5-氟-5-脱氧内酯，随后水解为5-FHPA。通过合成参考化合物，然后通过F-NMR和GC-MS分析进行共关联，证实了发酵液中5-FHPA的身份。5-FHPA的出现证明了一种新的氟代谢产物途径的存在。
