Synthesis of a proposed isomer of F<sub>420</sub> having α‐glutamyl bonding

Kimachi, Tetsutaro; Tanaka, Kiyoshi; Yoneda, Fumio

doi:10.1002/jhet.5570280244

Cited by 16 publications

(10 citation statements)

References 13 publications

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“…The physiological significance and biochemical basis for these differences is not yet understood. In some archaea, a terminal ␣-linked glutamate residue (126,127) is also added by ␥-F 420 -2:␣-L-glutamate ligase (CofF) (128), an enzyme of the ATP-grasp superfamily.…”

Section: Biosynthesismentioning

confidence: 99%

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

Greening

Ahmed

Mohamed

et al. 2016

Microbiol Mol Biol Rev

154

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: Biosynthesismentioning

confidence: 99%

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

Greening

Ahmed

Mohamed

et al. 2016

Microbiol Mol Biol Rev

154

208

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“…The anthracenyl, dansyl, and pyrenyl units 19 , 20 , and 21 are commercially available, and 20 and 21 were derivatized to obtain the alcohols 22 21 and 23 22. The deazaflavinyl alcohol 24 was synthesized from 6‐chlorouracil 25 23, 24 in three steps via 26 and 27 (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

Fluorescent Probes for Rapid Screening of Potential Drug–Drug Interactions at the CYP3A4 Level

et al. 2007

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Steroid derivatives bearing fluorescent groups such as anthracene, dansyl, deazaflavin, and pyrene attached to C6 were synthesized. These compounds are unique inhibitors of cytochrome P450 3A4 (CYP3A4) and display similar IC(50) values in the microM range for the CYP3A4 substrates midazolam, testosterone, and nifedipine. On binding to CYP3A4, the fluorescence of the dansyl, deazaflavin, and pyrene probes is quenched by photophysical interaction of the fluorophore with the heme. The addition of drug candidates with binding constants in the nM-microM range causes displacement of the probes from the active site, and hence leads to restoration of fluorescence. Accordingly, relative affinities of drug candidates to CYP3A4 can be easily and accurately determined by fluorescence measurements.

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“…[13] Subsequent treatment of the product 12 with the bis-benzyl-protected 2,4-dihydroxybenzaldehyde 13 [14] afforded the deazaflavin 14, which was alkylated to 15 with pentyl bromide to increase the solubility of the model compounds. Cleavage of the Boc group to yield 9 and reaction with the bis-carboxymethyl-substituted cyclobutane derivative, uracil dimer 16, [12] afforded the bis-deazaflavin model compound 7.…”

Section: Flavin-and Deazaflavin-containing Model Compounds Mimic the mentioning

confidence: 99%

Flavin- and Deazaflavin-Containing Model Compounds Mimic the Energy Transfer Step in Type-II DNA-Photolyases

Epple¹,

Carell²

1998

Angewandte Chemie International Edition

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Synthesis of a proposed isomer of F₄₂₀ having α‐glutamyl bonding

Abstract: A proposed isomer of redox coenzyme F420, having αglutamyl bonding, has been synthesized from 8‐benzyloxy‐10‐D‐ribityl‐5‐deazaflavin and α‐L‐glutamyl‐L‐glutamic acid moiety, by the phosphite triester approach followed by deprotection procedures.

Cited by 16 publications

References 13 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

Fluorescent Probes for Rapid Screening of Potential Drug–Drug Interactions at the CYP3A4 Level

Flavin- and Deazaflavin-Containing Model Compounds Mimic the Energy Transfer Step in Type-II DNA-Photolyases

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Synthesis of a proposed isomer of F420 having α‐glutamyl bonding

Abstract: A proposed isomer of redox coenzyme F420, having αglutamyl bonding, has been synthesized from 8‐benzyloxy‐10‐D‐ribityl‐5‐deazaflavin and α‐L‐glutamyl‐L‐glutamic acid moiety, by the phosphite triester approach followed by deprotection procedures.

Cited by 16 publications

References 13 publications

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

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

Fluorescent Probes for Rapid Screening of Potential Drug–Drug Interactions at the CYP3A4 Level

Flavin- and Deazaflavin-Containing Model Compounds Mimic the Energy Transfer Step in Type-II DNA-Photolyases

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Synthesis of a proposed isomer of F₄₂₀ having α‐glutamyl bonding

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

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