Identification of 5-Fluoro-5-Deoxy-Ribulose as a Shunt Fluorometabolite in Streptomyces sp. MA37

Linrui Wu; Ming Him Tong; Kwaku Kyeremeh; Hai Deng

doi:10.3390/biom10071023

Identification of 5-Fluoro-5-Deoxy-Ribulose as a Shunt Fluorometabolite in Streptomyces sp. MA37

Linrui Wu, Ming Him Tong, Kwaku Kyeremeh, Hai Deng^* (Corresponding Author)

^*Corresponding author for this work

Chemistry

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Abstract

A fluorometabolite, 5-fluoro-5-deoxy-D-ribulose (5-FDRul), from the culture broth of the soil bacterium Streptomyces sp. MA37, was identified through a combination of genetic manipulation, chemo-enzymatic synthesis and NMR comparison. Although 5-FDRul has been chemically synthesized before, it was not an intermediate or a shunt product in previous studies of fluorometalism in S. cattleya. Our study of MA37 demonstrates that 5-FDRul is a naturally occurring fluorometabolite, rendering it a new addition to this rare collection of natural products. The genetic inactivation of key biosynthetic genes involved in the fluorometabolisms in MA37 resulted in the increased accumulation of unidentified fluorometabolites as observed from 19F-NMR spectral comparison among the wild type (WT) of MA37 and the mutated variants, providing evidence of the presence of other new biosynthetic enzymes involved in the fluorometabolite pathway in MA37.

Original language	English
Article number	1023
Number of pages	11
Journal	Biomolecules
Volume	10
Issue number	7
DOIs	https://doi.org/10.3390/biom10071023
Publication status	Published - 10 Jul 2020

Bibliographical note

Funding: This study was funded by an IBioIC PhD studentship (L.W.), a Leverhulme Trust Research Project (H.D. and M.H.T., project no. RPG-2014-418), a Leverhulme Trust–Royal Society Africa award (K.K. and H.D., AA090088), the jointly funded UK Medical Research Council–UK Department for International Development
(MRC/DFID) concordat agreement African Research Leaders Award (K.K. and H.D., MR/S00520X/1), and the Royal Society–NSFC Newton Mobility Grant Award (IEC\NSFC\170617 to H.D.).

Keywords

fluorometabolites
5-FDRul
Streptomyces sp.
MA37
genetic manipulation
chemo-enzymatic synthesis
Genetic manipulation
Chemo-enzymatic synthesis
Fluorometabolites
Streptomyces sp. MA37

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Cite this

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title = "Identification of 5-Fluoro-5-Deoxy-Ribulose as a Shunt Fluorometabolite in Streptomyces sp. MA37",

abstract = "A fluorometabolite, 5-fluoro-5-deoxy-D-ribulose (5-FDRul), from the culture broth of the soil bacterium Streptomyces sp. MA37, was identified through a combination of genetic manipulation, chemo-enzymatic synthesis and NMR comparison. Although 5-FDRul has been chemically synthesized before, it was not an intermediate or a shunt product in previous studies of fluorometalism in S. cattleya. Our study of MA37 demonstrates that 5-FDRul is a naturally occurring fluorometabolite, rendering it a new addition to this rare collection of natural products. The genetic inactivation of key biosynthetic genes involved in the fluorometabolisms in MA37 resulted in the increased accumulation of unidentified fluorometabolites as observed from 19F-NMR spectral comparison among the wild type (WT) of MA37 and the mutated variants, providing evidence of the presence of other new biosynthetic enzymes involved in the fluorometabolite pathway in MA37. ",

keywords = "fluorometabolites, 5-FDRul, Streptomyces sp., MA37, genetic manipulation, chemo-enzymatic synthesis, Genetic manipulation, Chemo-enzymatic synthesis, Fluorometabolites, Streptomyces sp. MA37",

author = "Linrui Wu and Tong, {Ming Him} and Kwaku Kyeremeh and Hai Deng",

note = "Funding: This study was funded by an IBioIC PhD studentship (L.W.), a Leverhulme Trust Research Project (H.D. and M.H.T., project no. RPG-2014-418), a Leverhulme Trust–Royal Society Africa award (K.K. and H.D., AA090088), the jointly funded UK Medical Research Council–UK Department for International Development (MRC/DFID) concordat agreement African Research Leaders Award (K.K. and H.D., MR/S00520X/1), and the Royal Society–NSFC Newton Mobility Grant Award (IEC\NSFC\170617 to H.D.). ",

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N2 - A fluorometabolite, 5-fluoro-5-deoxy-D-ribulose (5-FDRul), from the culture broth of the soil bacterium Streptomyces sp. MA37, was identified through a combination of genetic manipulation, chemo-enzymatic synthesis and NMR comparison. Although 5-FDRul has been chemically synthesized before, it was not an intermediate or a shunt product in previous studies of fluorometalism in S. cattleya. Our study of MA37 demonstrates that 5-FDRul is a naturally occurring fluorometabolite, rendering it a new addition to this rare collection of natural products. The genetic inactivation of key biosynthetic genes involved in the fluorometabolisms in MA37 resulted in the increased accumulation of unidentified fluorometabolites as observed from 19F-NMR spectral comparison among the wild type (WT) of MA37 and the mutated variants, providing evidence of the presence of other new biosynthetic enzymes involved in the fluorometabolite pathway in MA37.

AB - A fluorometabolite, 5-fluoro-5-deoxy-D-ribulose (5-FDRul), from the culture broth of the soil bacterium Streptomyces sp. MA37, was identified through a combination of genetic manipulation, chemo-enzymatic synthesis and NMR comparison. Although 5-FDRul has been chemically synthesized before, it was not an intermediate or a shunt product in previous studies of fluorometalism in S. cattleya. Our study of MA37 demonstrates that 5-FDRul is a naturally occurring fluorometabolite, rendering it a new addition to this rare collection of natural products. The genetic inactivation of key biosynthetic genes involved in the fluorometabolisms in MA37 resulted in the increased accumulation of unidentified fluorometabolites as observed from 19F-NMR spectral comparison among the wild type (WT) of MA37 and the mutated variants, providing evidence of the presence of other new biosynthetic enzymes involved in the fluorometabolite pathway in MA37.

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Identification of 5-Fluoro-5-Deoxy-Ribulose as a Shunt Fluorometabolite in Streptomyces sp. MA37

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