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Actinorhodin

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Actinorhodin
Names
Preferred IUPAC name 2,2′-pyran]-3,3′-diyl]diacetic acid
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 76401
ChEBI
ChemSpider
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C32H26O14/c1-9-21-15(3-11(45-9)5-19(35)36)29(41)23-17(33)7-13(27(39)25(23)31(21)43)14-8-18(34)24-26(28(14)40)32(44)22-10(2)46-12(6-20(37)38)4-16(22)30(24)42/h7-12,33-34,39-40H,3-6H2,1-2H3,(H,35,36)(H,37,38)/t9-,10-,11+,12+/m1/s1Key: VTIKDEXOEJDMJP-WYUUTHIRSA-N
  • InChI=1/C32H26O14/c1-9-21-15(3-11(45-9)5-19(35)36)29(41)23-17(33)7-13(27(39)25(23)31(21)43)14-8-18(34)24-26(28(14)40)32(44)22-10(2)46-12(6-20(37)38)4-16(22)30(24)42/h7-12,33-34,39-40H,3-6H2,1-2H3,(H,35,36)(H,37,38)/t9-,10-,11+,12+/m1/s1Key: VTIKDEXOEJDMJP-WYUUTHIRBL
SMILES
  • OC(=O)C5CC=6C(=O)c4c(O)cc(c3cc(O)c2C(=O)C=1C(CC(O)=O)O(C)C=1C(=O)c2c3O)c(O)c4C(=O)C=6(C)O5
Properties
Chemical formula C32H26O14
Molar mass 634.546 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Actinorhodin is a benzoisochromanequinone dimer polyketide antibiotic produced by Streptomyces coelicolor. The gene cluster responsible for actinorhodin production contains the biosynthetic enzymes and genes responsible for export of the antibiotic. The antibiotic also has the effect of being a pH indicator due to its pH-dependent color change. It is a product of a Type II polyketide synthase biosynthetic pathway.

References

  1. Magnolo SK, Leenutaphong DL, DeModena JA, et al. (May 1991). "Actinorhodin production by Streptomyces coelicolor and growth of Streptomyces lividans are improved by the expression of a bacterial hemoglobin". Bio/Technology. 9 (5): 473–6. doi:10.1038/nbt0591-473. PMID 1367312. S2CID 21623645.
  2. Brian P, Riggle PJ, Santos RA, Champness WC (June 1996). "Global negative regulation of Streptomyces coelicolor antibiotic synthesis mediated by an absA-encoded putative signal transduction system". J. Bacteriol. 178 (11): 3221–31. doi:10.1128/jb.178.11.3221-3231.1996. PMC 178074. PMID 8655502.
  3. Tahlan, K; Ahn SK; Sing A; Bodnaruk TD; Willems AR; Davidson AR; Nodwell JR. (February 2007). "Initiation of actinorhodin export in Streptomyces coelicolor". Molecular Microbiology. 63 (4): 951–961. doi:10.1111/j.1365-2958.2006.05559.x. PMID 17338074.
  4. Bystrykh, LV; Fernández-Moreno MA; Herrema JK; Malpartida F; Hopwood DA; Dijkhuizen L (April 1996). "Production of actinorhodin-related "blue pigments" by Streptomyces coelicolor A3(2)". Journal of Bacteriology. 178 (8): 2238–44. doi:10.1128/jb.178.8.2238-2244.1996. PMC 177931. PMID 8636024.
  5. Javidpour, Pouya; Bruegger, Joel; Srithahan, Supawadee; Korman, Tyler P.; Crump, Matthew P.; Crosby, John; Burkart, Michael D.; Tsai, Shiou-Chuan (2013). "The Determinants of Activity and Specificity in Actinorhodin Type II Polyketide Ketoreductase". Chemistry & Biology. 20 (10): 1225–1234. doi:10.1016/j.chembiol.2013.07.016. PMC 3855848. PMID 24035284.
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