Chromomycin A3 (CMA3) or Toyomycin is an anthraquinone antibiotic glycoside produced by the fermentation of a certain strain of Streptomyces griseus (No. 7).[1]
Names | |
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IUPAC name
(6S,7S)-6-[(4-O-Acetyl-2,6-dideoxy-3-C-methyl-α-L-arabino-hexopyranosyl)-(1→3)-(2,6-dideoxy-β-D-arabino-hexopyranosyl)-(1→3)-2,6-dideoxy-β-D-arabino-hexopyranosyloxy]-7-[(1S)-5-deoxy-1-O-methyl-D-threo-pent-2-ulos-1-C-yl]-4,10-dihydroxy-3-methyl-5-oxo-5,6,7,8-tetrahydroanthracen-2-yl (2,6-dideoxy-4-O-methyl-D-lyxo-hexopyranosyl)-(1→3)-2,6-dideoxy-D-lyxo-hexopyranoside 4-acetate
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Systematic IUPAC name
(12S,14S,15S,16S,32S,34R,35R,36R,52S,54R,55R,56R,72S,73S,92S,94R,95S,96R,112R,114R,115R,116R)-73-[(1S,3S,4R)-3,4-Dihydroxy-1-methoxy-2-oxopentyl]-14,35,55,78,79,114-heptahydroxy-115-methoxy-14,16,36,56,77,96,116-heptamethyl-71-oxo-71,72,73,74-tetrahydro-2,4,6,8,10-pentaoxa-1,11(2),3,5(4,2),9(2,4)-pentakis(oxana)-7(2,6)-anthracenaundecaphane-15,95-diyl diacetate | |
Other names
Toyomycin
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Identifiers | |
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ECHA InfoCard | 100.027.589 |
PubChem CID
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UNII |
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CompTox Dashboard (EPA)
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Properties | |
C57H82O26 | |
Molar mass | 1183.257 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
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In the presence of Mg2+ ions, Chromomycin A3 binds reversibly to DNA, preferentially to contiguous G/C base pairs.[2][3]
When bound to DNA, Chromomycin A3 has a maximum excitation wavelength of 445 nm (blue), and a maximum emission wavelength of 575 nm (yellow).[4]