Identification of a fluorometabolite from Streptomyces sp. MA37: (2R3S4S)-5-fluoro-2,3,4-trihydroxypentanoic acid.
Identification of a fluorometabolite from Streptomyces sp. MA37: (2R3S4S)-5-fluoro-2,3,4-trihydroxypentanoic acid.
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DOI：
10.1039/c4sc03540b
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发表时间：
2015-02-01
期刊：
影响因子：
8.4
通讯作者：
O'Hagan D
中科院分区：
文献类型：
--
作者：
Ma L;Bartholome A;Tong MH;Qin Z;Yu Y;Shepherd T;Kyeremeh K;Deng H;O'Hagan D
（2 R3 S4 S）-5-氟-2，3，4-三羟基戊酸（5-FHPA）是在土壤细菌链霉菌（Streptomycessp.MA37）中发现的一种新的氟代代谢物。（2 R3 S4 S）-5-氟-2，3，4-三羟基戊酸（5-FHPA）是在土壤细菌链霉菌（Streptomycessp.MA37）中发现的一种新的氟代代谢物。将5-氟-5-脱氧-d-核糖（5-FDR）外源添加到MA 37的无细胞提取物中证明5-FDR是一系列未鉴定的氟代代谢物的中间体，不同于氟乙酸盐（FAc）和4-氟代苏氨酸（4-FT）。生物信息学分析允许鉴定基因簇（fdr），其编码5-FHPA的生物合成途径。FdrC的过表达和体外测定表明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，然后水解为5-FHPA。通过合成参比化合物，然后通过19 F-NMR和GC-MS分析进行相关性分析，确认发酵液中5-FHPA的身份。5-FHPA的出现证明了新的氟代谢途径的存在。
(2R3S4S)-5-Fluoro-2,3,4-trihydroxypentanoic acid (5-FHPA) has been discovered as a new fluorometabolite in the soil bacterium Streptomyces sp. MA37. (2R3S4S)-5-Fluoro-2,3,4-trihydroxypentanoic acid (5-FHPA) has been discovered as a new fluorometabolite in the soil bacterium Streptomyces 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 (fdr), encoding a pathway to the biosynthesis of 5-FHPA. Over-expression and in vitro 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 19F-NMR and GC-MS analysis. The occurrence of 5-FHPA proves the existence of a new fluorometabolite pathway.
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影响因子：
5.1
作者：
Eustaquio, Alessandra S.;O'Hagan, David;Moore, Bradley S.
通讯作者：
Moore, Bradley S.
影响因子：
2.1
作者：
Fusaro, Maxime B.;Chagnault, Vincent;Postel, Denis
通讯作者：
Postel, Denis
影响因子：
3.5
作者：
Fenical, William;Jensen, Paul R.;Palladino, Michael A.;Lam, Kin S.;Lloyd, G. Kenneth;Potts, Barbara C.
通讯作者：
Potts, Barbara C.
影响因子：
5.1
作者：
Jaivel, Nanjundan;Uvarani, Chokkalingam;Marimuthu, Ponnusamy
通讯作者：
Marimuthu, Ponnusamy
影响因子：
3.8
作者：
OHAGAN, D;PERRY, R;HARPER, DB
通讯作者：
HARPER, DB