13925-12-7

Basic information

• Product Name: myxin
• Synonyms: myxin;1-Hydroxy-6-methoxyphenazine 5,10-dioxide;3C-Antibiotic;6-Methoxy-1-phenazinol 5,10-dioxide;6-Methoxy-1-phenazinol-5,10-dioxide
• CAS NO: 13925-12-7
• Molecular Formula: C₁₃H₁₀N₂O₄
• Molecular Weight: 258.232
• Mol File: 13925-12-7.mol
• Article Data: 7

Chemical Properties

• Melting Point: 120-130°; mp 149° (dec) (Sigg, Toth)
• Boiling Point: 401.48°C (rough estimate)
• Flash Point: 279.7°C
• Appearance: /
• Density: 1.2944 (rough estimate)
• Vapor Pressure: 1.93E-12mmHg at 25°C
• Refractive Index: 1.5300 (estimate)
• CAS DataBase Reference: myxin(CAS DataBase Reference)
• NIST Chemistry Reference: myxin(13925-12-7)
• EPA Substance Registry System: myxin(13925-12-7)

Safety Data

• Hazardous Substances Data: 13925-12-7(Hazardous Substances Data)

Usage

Chemical Properties

Reddish, acicular crystals. Evolves heat near 150C and can decompose withexplosive violence at this temperature, soluble inacetone.

Uses

Bacteriostat and antifungal agent, antibiotic.

InChI:InChI=1/C13H10N2O4/c1-19-11-7-3-5-9-13(11)15(18)8-4-2-6-10(16)12(8)14(9)17/h2-7,18H,1H3

Upstream product

• 69-86-3 1,6-dihydroxyphenazine N₅-monooxide 
• 23462-25-1 phenazine-1,6-dicarboxylic acid 
• 68-81-5 iodinin 
• 485-80-3 S-adenosyl-L-methionine 
• 74-88-4 methyl iodide 
• 112970-44-2 2-bromo-3-methoxyaniline 
• 69-48-7 phenazine-1,6-diol 
• 13925-11-6 1,6-dimethoxyphenazine-N₅,N 10-dioxide 
• 13129-58-3 1-hydroxy-6-methoxyphenazine 
• 90-04-0 2-methoxy-phenylamine 
• 13398-79-3 1,6-dimethoxyphenazine 
• 91-23-6 2-Nitroanisole 

Relevant articles and documents

The structure of myxin.

-

Functional and Structural Analysis of Phenazine O -Methyltransferase LaPhzM from Lysobacter antibioticus OH13 and One-Pot Enzymatic Synthesis of the Antibiotic Myxin

Myxin is a well-known antibiotic that had been used for decades. It belongs to the phenazine natural products that exhibit various biological activities, which are often dictated by the decorating groups on the heteroaromatic three-ring system. The three rings of myxin carry a number of decorations, including an unusual aromatic N5,N10-dioxide. We previously showed that phenazine 1,6-dicarboxylic acid (PDC) is the direct precursor of myxin, and two redox enzymes (LaPhzS and LaPhzNO1) catalyze the decarboxylative hydroxylation and aromatic N-oxidations of PDC to produce iodinin (1.6-dihydroxy-N5,N10-dioxide phenazine). In this work, we identified the LaPhzM gene from Lysobacter antibioticus OH13 and demonstrated that LaPhzM encodes a SAM-dependent O-methyltransferase converting iodinin to myxin. The results further showed that LaPhzM is responsible for both monomethoxy and dimethoxy formation in all phenazine compounds isolated from strain OH13. LaPhzM exhibits relaxed substrate selectivity, catalyzing O-methylation of phenazines with non-, mono-, or di-N-oxide. In addition, we demonstrated a one-pot biosynthesis of myxin by in vitro reconstitution of the three phenazine-ring decorating enzymes. Finally, we determined the X-ray crystal structure of LaPhzM with a bound cofactor at 1.4 ? resolution. The structure provided molecular insights into the activity and selectivity of the first characterized phenazine O-methyltransferase. These results will facilitate future exploitation of the thousands of phenazines as new antibiotics through metabolic engineering and chemoenzymatic syntheses.

COMPOUNDS

The invention provides novel phenazine derivatives, methods for their preparation and their medical use, in particular as anti-neoplastic agents and anti- infective agents. The invention further relates to novel methods for the preparation of iodinin and

Method for the purification of 6-methoxy-1-phenazinol 5,10-dioxide

A novel improved procedure is described for the preparation of various metal complexes of 6-methoxy-1-phenazinol 5,10-dioxide by the reaction between 6-methoxy-1-phenazinol 5,10-dioxide and a metal salt or hydroxide in an aqueous suspension or a solution in aqueous mineral acid. Preferred metals disclosed as suitable for use in the process are calcium, strontium, magnesium and iron. Utility of the ferric chloride complex and the calcium complex in the purification of 6-methoxy-1-phenazinol 5,10-dioxide is also disclosed.