Identity of cosynthetic factor I of Streptomyces aureofaciens and fragment FO from coenzyme F420 of Methanobacterium species

McCormick, J. R. D.; Morton, George O.

doi:10.1021/ja00378a044

Cited by 80 publications

(52 citation statements)

References 2 publications

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“…As far back as 1960, McCormick et al isolated a hydride-transferring cofactor mediating tetracycline biosynthesis (24,(381)(382)(383), now known to be F 420 (29,122,384). A combination of genetic and biochemical studies have since shown that an F 420 H 2 -dependent reductase (OxyR) catalyzes the final step of oxytetracycline biosynthesis (385), namely, reduction of the C-5aϭC-11a double bond of dehydrooxytetracycline ( Fig.…”

Section: Streptomycetesmentioning

confidence: 99%

“…While it has been proposed that FDOR-A proteins are F 420 H 2 -dependent menaquinone reductases (32), to date, activity has been observed only with nonphysiological quinones (e.g., menadione), rather than with menaquinone (30,32); hence, it is unclear whether these enzymes have primarily evolved to input electrons into the respiratory chain or instead detoxify exogenous redox cycling agents (section 4.1.1). Finally, it was recently shown that the F 420 H 2 -dependent step in the biosynthesis of antibiotics of the tetracycline, oxotetracycline, and chlortetracycline classes (122,381,382,384 420 -reducing glucose-6-phosphate dehydrogenase (Fgd), and F 420 -reducing hydroxymycolic acid dehydrogenase (fHMAD). However, comparative genome analysis indicates that there are numerous other F 420 -dependent LLHTs in actinomycetes, the majority probably serving as reductases (37).…”

Section: Fdors: Flavin/deazaflavin Oxidoreductase Superfamilymentioning

confidence: 99%

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Physiology, Biochemistry, and Applications of F₄₂₀- and F_o-Dependent Redox Reactions

Greening

Ahmed

Mohamed

et al. 2016

Microbiol Mol Biol Rev

159

208

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SUMMARY5-Deazaflavin cofactors enhance the metabolic flexibility of microorganisms by catalyzing a wide range of challenging enzymatic redox reactions. While structurally similar to riboflavin, 5-deazaflavins have distinctive and biologically useful electrochemical and photochemical properties as a result of the substitution of N-5 of the isoalloxazine ring for a carbon. 8-Hydroxy-5-deazaflavin (Fo) appears to be used for a single function: as a light-harvesting chromophore for DNA photolyases across the three domains of life. In contrast, its oligoglutamyl derivative F420is a taxonomically restricted but functionally versatile cofactor that facilitates many low-potential two-electron redox reactions. It serves as an essential catabolic cofactor in methanogenic, sulfate-reducing, and likely methanotrophic archaea. It also transforms a wide range of exogenous substrates and endogenous metabolites in aerobic actinobacteria, for example mycobacteria and streptomycetes. In this review, we discuss the physiological roles of F420in microorganisms and the biochemistry of the various oxidoreductases that mediate these roles. Particular focus is placed on the central roles of F420in methanogenic archaea in processes such as substrate oxidation, C1pathways, respiration, and oxygen detoxification. We also describe how two F420-dependent oxidoreductase superfamilies mediate many environmentally and medically important reactions in bacteria, including biosynthesis of tetracycline and pyrrolobenzodiazepine antibiotics by streptomycetes, activation of the prodrugs pretomanid and delamanid byMycobacterium tuberculosis, and degradation of environmental contaminants such as picrate, aflatoxin, and malachite green. The biosynthesis pathways of Foand F420are also detailed. We conclude by considering opportunities to exploit deazaflavin-dependent processes in tuberculosis treatment, methane mitigation, bioremediation, and industrial biocatalysis.

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Section: Streptomycetesmentioning

confidence: 99%

Section: Fdors: Flavin/deazaflavin Oxidoreductase Superfamilymentioning

confidence: 99%

Physiology, Biochemistry, and Applications of F₄₂₀- and F_o-Dependent Redox Reactions

Greening

Ahmed

Mohamed

et al. 2016

Microbiol Mol Biol Rev

159

208

View full text Add to dashboard Cite

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“…A single 34-kb DNA segment allowed heterologous expression of OTC biosynthesis in S. lividans (29), showing the presence of a single OTC cluster. Cross-feeding experiments (200) showed that some of the mutants in the second region (csf mutants) were defective in the synthesis of an essential flavin cofactor, cosynthesis factor 1 (146,147,154).…”

Section: Chromosomal Linkage Mappingmentioning

confidence: 99%

Genetics ofStreptomyces rimosus, the Oxytetracycline Producer

Petković

Cullum

Hranueli

et al. 2006

Microbiol Mol Biol Rev

101

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SUMMARY From a genetic standpoint, Streptomyces rimosus is arguably the best-characterized industrial streptomycete as the producer of oxytetracycline and other tetracycline antibiotics. Although resistance to these antibiotics has reduced their clinical use in recent years, tetracyclines have an increasing role in the treatment of emerging infections and noninfective diseases. Procedures for in vivo and in vitro genetic manipulations in S. rimosus have been developed since the 1950s and applied to study the genetic instability of S. rimosus strains and for the molecular cloning and characterization of genes involved in oxytetracycline biosynthesis. Recent advances in the methodology of genome sequencing bring the realistic prospect of obtaining the genome sequence of S. rimosus in the near term.

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“…After the structure of LCFwas assigned, a literature search revealed that I has been reported previously as a cosynthetic factor in tetracycline biosynthesis. 6) Comparison of spectroscopic data (IR, 13C NMR, XH NMR, UVvis) convinced us that LCF was identical to cosynthetic factor 1. After this work was completed, a report by Daniels et alP describing the presence of a 5-deazaflavin co factor in nine species of Streptomyces and one Nocardia species was called to our attention.…”

mentioning

confidence: 90%

Isolation and identification of 7,8-didemethyl-8-hydroxy-5-deazariboflavin, an unusual cosynthetic factor in streptomycetes, from Streptomyces lincolnensis.

et al. 1989

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Identity of cosynthetic factor I of Streptomyces aureofaciens and fragment FO from coenzyme F420 of Methanobacterium species

Cited by 80 publications

References 2 publications

Physiology, Biochemistry, and Applications of F₄₂₀- and F_o-Dependent Redox Reactions

Physiology, Biochemistry, and Applications of F₄₂₀- and F_o-Dependent Redox Reactions

Genetics ofStreptomyces rimosus, the Oxytetracycline Producer

Isolation and identification of 7,8-didemethyl-8-hydroxy-5-deazariboflavin, an unusual cosynthetic factor in streptomycetes, from Streptomyces lincolnensis.

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Identity of cosynthetic factor I of Streptomyces aureofaciens and fragment FO from coenzyme F420 of Methanobacterium species

Cited by 80 publications

References 2 publications

Physiology, Biochemistry, and Applications of F420- and Fo-Dependent Redox Reactions

Physiology, Biochemistry, and Applications of F420- and Fo-Dependent Redox Reactions

Genetics ofStreptomyces rimosus, the Oxytetracycline Producer

Isolation and identification of 7,8-didemethyl-8-hydroxy-5-deazariboflavin, an unusual cosynthetic factor in streptomycetes, from Streptomyces lincolnensis.

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Physiology, Biochemistry, and Applications of F₄₂₀- and F_o-Dependent Redox Reactions

Physiology, Biochemistry, and Applications of F₄₂₀- and F_o-Dependent Redox Reactions