Roseoflavin (CAS 51093-55-1)
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Roseoflavin, a natural riboflavin (vitamin B2) analog, is primarily sourced from the bacterium Streptomyces davawensis. Its structural similarity to riboflavin allows it to competitively inhibit flavin mononucleotide (FMN) and flavin adenine dinucleotide (FAD) synthesis, pivotal cofactors in various enzymatic reactions, including those involved in the oxidative metabolism and electron transport chain. In research, roseoflavin′s mechanism of action is harnessed to study the regulatory roles of FMN and FAD in cellular processes, offering insights into the modulation of metabolic pathways and electron transport systems. This compound serves as a tool in molecular biology to understand the intricacies of flavoprotein function and their contribution to cellular redox states, energy production, and metabolic regulation. By interfering with riboflavin metabolism, roseoflavin provides a unique approach to elucidate the biological significance of vitamin B2 in various organisms, including its impact on bacterial growth and survival, which aids in the exploration of antimicrobial targets.
Roseoflavin (CAS 51093-55-1) References
- The bifunctional flavokinase/flavin adenine dinucleotide synthetase from Streptomyces davawensis produces inactive flavin cofactors and is not involved in resistance to the antibiotic roseoflavin. | Grill, S., et al. 2008. J Bacteriol. 190: 1546-53. PMID: 18156273
- Roseoflavin is a natural antibacterial compound that binds to FMN riboswitches and regulates gene expression. | Lee, ER., et al. 2009. RNA Biol. 6: 187-94. PMID: 19246992
- The RFN riboswitch of Bacillus subtilis is a target for the antibiotic roseoflavin produced by Streptomyces davawensis. | Ott, E., et al. 2009. RNA Biol. 6: 276-80. PMID: 19333008
- A highly specialized flavin mononucleotide riboswitch responds differently to similar ligands and confers roseoflavin resistance to Streptomyces davawensis. | Pedrolli, DB., et al. 2012. Nucleic Acids Res. 40: 8662-73. PMID: 22740651
- Genome sequence of the bacterium Streptomyces davawensis JCM 4913 and heterologous production of the unique antibiotic roseoflavin. | Jankowitsch, F., et al. 2012. J Bacteriol. 194: 6818-27. PMID: 23043000
- The flavoenzyme azobenzene reductase AzoR from Escherichia coli binds roseoflavin mononucleotide (RoFMN) with high affinity and is less active in its RoFMN form. | Langer, S., et al. 2013. Biochemistry. 52: 4288-95. PMID: 23713585
- Flavoproteins are potential targets for the antibiotic roseoflavin in Escherichia coli. | Langer, S., et al. 2013. J Bacteriol. 195: 4037-45. PMID: 23836860
- Identification of the Key Enzyme of Roseoflavin Biosynthesis. | Schwarz, J., et al. 2016. Angew Chem Int Ed Engl. 55: 6103-6. PMID: 27062037
- Characterization of the small flavin-binding dodecin in the roseoflavin producer Streptomyces davawensis. | Ludwig, P., et al. 2018. Microbiology (Reading). 164: 908-919. PMID: 29856311
- Metabolic engineering of roseoflavin-overproducing microorganisms. | Mora-Lugo, R., et al. 2019. Microb Cell Fact. 18: 146. PMID: 31451111
- The roseoflavin producer Streptomyces davaonensis has a high catalytic capacity and specific genetic adaptations with regard to the biosynthesis of riboflavin. | Kißling, L., et al. 2020. Environ Microbiol. 22: 3248-3265. PMID: 32410282
- A second riboflavin import system is present in flavinogenic Streptomyces davaonensis and supports roseoflavin biosynthesis. | Schneider, C. and Mack, M. 2021. Mol Microbiol. 116: 470-482. PMID: 33829573
- Affinity-Based Profiling of the Flavin Mononucleotide Riboswitch. | Crielaard, S., et al. 2022. J Am Chem Soc. 144: 10462-10470. PMID: 35666649
- Roseoflavin, a Natural Riboflavin Analogue, Possesses In Vitro and In Vivo Antiplasmodial Activity. | Hemasa, AL., et al. 2022. Antimicrob Agents Chemother. 66: e0054022. PMID: 36094195
Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
Roseoflavin, 2.5 mg | sc-208315A | 2.5 mg | $124.00 | |||
Roseoflavin, 5 mg | sc-208315B | 5 mg | $146.00 | |||
Roseoflavin, 10 mg | sc-208315C | 10 mg | $208.00 | |||
Roseoflavin, 25 mg | sc-208315 | 25 mg | $336.00 | |||
Roseoflavin, 100 mg | sc-208315D | 100 mg | $936.00 | |||
Roseoflavin, 250 mg | sc-208315E | 250 mg | $1399.00 |