Roseoflavin
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| Category | Antibiotics |
| Catalog number | BBF-02637 |
| CAS | 51093-55-1 |
| Molecular Weight | 405.40 |
| Molecular Formula | C18H23N5O6 |
| Purity | >98% by HPLC |
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Description
An antibacterial pigment isolated from streptomyces davawensis; an anti-metabolite of riboflavin; mimic riboflavin in flavin biosynthesis; an important regulator of bacterial gene expression by binding to untranslated regions of RNA, so-called ribo-switching sites.
Specification
| Synonyms | 8-demethyl-8-(dimethylamino)riboflavin; 1-Deoxy-1-[8-(Dimethylamino)-7-Methyl-2,4-Dioxo-3,4-Dihydrobenzo[g]pteridin-10(2h)-Yl]-D-Ribitol; Roseoflavine; 8-Dimethylaminoriboflavin |
| Storage | Store at -20°C |
| IUPAC Name | 8-(dimethylamino)-7-methyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]benzo[g]pteridine-2,4-dione |
| Canonical SMILES | CC1=CC2=C(C=C1N(C)C)N(C3=NC(=O)NC(=O)C3=N2)CC(C(C(CO)O)O)O |
| InChI | InChI=1S/C18H23N5O6/c1-8-4-9-11(5-10(8)22(2)3)23(6-12(25)15(27)13(26)7-24)16-14(19-9)17(28)21-18(29)20-16/h4-5,12-13,15,24-27H,6-7H2,1-3H3,(H,21,28,29)/t12-,13+,15-/m0/s1 |
| InChI Key | IGQLDUYTWDABFK-GUTXKFCHSA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | Dark Red Solid |
| Boiling Point | 732.66°C at 760 mmHg |
| Melting Point | 276-278°C |
| Density | 1.59 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF or DMSO. Limited water solubility. |
Reference Reading
1.Flavoproteins are potential targets for the antibiotic roseoflavin in Escherichia coli.
Langer S1, Hashimoto M, Hobl B, Mathes T, Mack M. J Bacteriol. 2013 Sep;195(18):4037-45. doi: 10.1128/JB.00646-13. Epub 2013 Jul 8.
The riboflavin analog roseoflavin is an antibiotic produced by Streptomyces davawensis. Riboflavin transporters are responsible for roseoflavin uptake by target cells. Roseoflavin is converted to the flavin mononucleotide (FMN) analog roseoflavin mononucleotide (RoFMN) by flavokinase and to the flavin adenine dinucleotide (FAD) analog roseoflavin adenine dinucleotide (RoFAD) by FAD synthetase. In order to study the effect of RoFMN and RoFAD in the cytoplasm of target cells, Escherichia coli was used as a model. E. coli is predicted to contain 38 different FMN- or FAD-dependent proteins (flavoproteins). These proteins were overproduced in recombinant E. coli strains grown in the presence of sublethal amounts of roseoflavin. The flavoproteins were purified and analyzed with regard to their cofactor contents. It was found that 37 out of 38 flavoproteins contained either RoFMN or RoFAD. These cofactors have different physicochemical properties than FMN and FAD and were reported to reduce or completely abolish flavoprotein function.
2.Natural riboflavin analogs.
Pedrolli DB1, Jankowitsch F, Schwarz J, Langer S, Nakanishi S, Mack M. Methods Mol Biol. 2014;1146:41-63. doi: 10.1007/978-1-4939-0452-5_3.
Riboflavin analogs have a good potential to serve as basic structures for the development of novel anti-infectives. Riboflavin analogs have multiple cellular targets, since riboflavin (as a precursor to flavin cofactors) is active at more than one site in the cell. As a result, the frequency of developing resistance to antimicrobials based on riboflavin analogs is expected to be significantly lower. The only known natural riboflavin analog with antibiotic function is roseoflavin from the bacterium Streptomyces davawensis. This antibiotic negatively affects flavoenzymes and FMN riboswitches. Another roseoflavin producer, Streptomyces cinnabarinus, was recently identified. Possibly, flavin analogs with antibiotic activity are more widespread than anticipated. The same could be true for flavin analogs yet to be discovered, which could constitute tools for cellular chemistry, thus allowing a further extension of the catalytic spectrum of flavoenzymes.
3.Photoinduced intramolecular charge transfer in an electronically modified flavin derivative: roseoflavin.
Karasulu B1, Thiel W. J Phys Chem B. 2015 Jan 22;119(3):928-43. doi: 10.1021/jp506101x. Epub 2014 Sep 26.
The photophysical properties of a push-pull flavin derivative, roseoflavin (RoF), are investigated in different surroundings at the molecular level, with focus on intramolecular charge transfer (ICT). Time-dependent density functional theory (TD-DFT, CAM-B3LYP functional) and DFT-based multireference configuration interaction (DFT/MRCI) are used to compute excited-state energies and one-electron properties of a truncated RoF model, roseolumiflavin (RoLF). Solvent effects are taken into account implicitly by the conductor-like polarizable continuum model and explicitly through a microsolvation scheme. In the gas phase, the calculations predict no crossing between the lowest locally excited (LE) and charge-transfer (CT) states upon twisting the dimethylamine donor group relative to the plane of the isoalloxazine acceptor moiety, whereas this crossing is found to be facile in solution (i.e., in water or benzene). Crossing of the LE and CT states facilitates ICT, which is the main cause of the fluorescence quenching and dual fluorescence character experimentally observed for roseoflavin in solution.
4.Bacterial flavin mononucleotide riboswitches as targets for flavin analogs.
Pedrolli DB1, Mack M. Methods Mol Biol. 2014;1103:165-76. doi: 10.1007/978-1-62703-730-3_13.
Roseoflavin is a toxic riboflavin (vitamin B2) analog and naturally is produced by Streptomyces davawensis. Roseoflavin is converted to roseoflavin mononucleotide (RoFMN) by promiscuous flavokinases (EC 2.7.1.26). Flavin mononucleotide (FMN) riboswitches control the expression of genes involved in riboflavin biosynthesis and/or transport. RoFMN triggers FMN riboswitches and negatively (or positively) affects expression of the downstream genes. RoFMN binding to the aptamer portion of FMN riboswitch RNAs occurs in the course of transcription by cellular RNA polymerases. We developed an in vitro test system to functionally characterize the interaction between riboflavin/FMN analogs such as roseoflavin/RoFMN and FMN riboswitches in the context of an actively transcribing RNA polymerase.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
