28399-50-0

Basic information

• Product Name: rabelomycin
• Synonyms: rabelomycin;(-)-3,4-Dihydro-3,6,8-trihydroxy-3-methylbenz[a]anthracene-1,7,12(2H)-trione
• CAS NO: 28399-50-0
• Molecular Formula: C19H14O6
• Molecular Weight: 0
• Mol File: 28399-50-0.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 675.7°Cat760mmHg
• Flash Point: 376.4°C
• Appearance: /
• Density: 1.576g/cm³
• Vapor Pressure: 3.52E-19mmHg at 25°C
• Refractive Index: 1.728
• CAS DataBase Reference: rabelomycin(CAS DataBase Reference)
• NIST Chemistry Reference: rabelomycin(28399-50-0)
• EPA Substance Registry System: rabelomycin(28399-50-0)

Safety Data

• Hazardous Substances Data: 28399-50-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C19H14O6/c1-19(25)6-8-5-11(21)15-16(13(8)12(22)7-19)17(23)9-3-2-4-10(20)14(9)18(15)24/h2-5,20-21,25H,6-7H2,1H3/t19-/m1/s1

Upstream product

• 1193-18-6 3-methylcyclohexen-2-one 
• 155652-44-1 6-ethoxy-1,2,3,4-tetrahydro-8-hydroxy-3-methyl-3-(pentamethyldisilanyl)benzoanthracen-7,12-dione 
• 155652-45-2 1,2,3,4-tetrahydro-6,8-dihydroxy-3-methyl-3-(hydroxydimethylsilanyl)benzoanthracen-7,12-dione 
• 155652-41-8 ethyl (E/Z)-<3-methyl-3-(pentamethyldisilanyl)cyclohexylidene>acetate 
• 155652-39-4 3-Methyl-3-(1,1,2,2,2-pentamethyl-disilanyl)-cyclohexanone 
• 155652-46-3 rac-1-deoxyrabelomycin 

Relevant articles and documents

Engineering anthracycline biosynthesis toward angucyclines

The biosynthesis pathways of two anthracyclines, nogalamycin and aclacinomycin, were directed toward angucyclines by using an angucycline-specific cyclase, pgaF, isolated from a silent antibiotic biosynthesis gene cluster. Addition of pgaF to a gene cassette that harbored the early biosynthesis genes of nogalamycin resulted in the production of two known angucyclinone metabolites, rabelomycin and its precursor, UWM6. Substrate flexibility of pgaF was demonstrated by replacement of the nogalamycin minimal polyketide synthase genes in the gene cassette with the equivalent aclacinomycin genes together with aknE2 and aknF, which specify the unusual propionate starter unit in aclacinomycin biosynthesis. This modification led to the production of a novel angucyclinone, MM2002, in which the expected ethyl side chain was incorporated into the fourth ring.

Erste Totalsynthese von (+/-)-Rabelomycin

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