Actinorhodin

Last updated
Actinorhodin
Actinorhodin.svg
Names
Preferred IUPAC name
2,2′-[(1R,1′R,3S,3′S)-5,5′,10,10′-Tetrahydroxy-6,6′,9,9′-tetraoxo-3,3′,4,4′,6,6′,9,9′-octahydro-1H,1′H-[8,8′-binaphtho[2,3-c]pyran]-3,3′-diyl]diacetic acid
Identifiers
3D model (JSmol)
76401
ChEBI
ChemSpider
KEGG
PubChem CID
UNII
  • 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/s1 Yes check.svgY
    Key: VTIKDEXOEJDMJP-WYUUTHIRSA-N Yes check.svgY
  • 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/s1
    Key: VTIKDEXOEJDMJP-WYUUTHIRBL
  • OC(=O)C[C@@H]5CC=6C(=O)c4c(O)cc(c3cc(O)c2C(=O)C=1C[C@@H](CC(O)=O)O[C@H](C)C=1C(=O)c2c3O)c(O)c4C(=O)C=6[C@@H](C)O5
Properties
C32H26O14
Molar mass 634.546 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Actinorhodin is a benzoisochromanequinone dimer polyketide antibiotic produced by Streptomyces coelicolor . [1] [2] The gene cluster responsible for actinorhodin production contains the biosynthetic enzymes and genes responsible for export of the antibiotic. [3] The antibiotic also has the effect of being a pH indicator due to its pH-dependent color change. [4] It is a product of a Type II polyketide synthase biosynthetic pathway. [5]

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.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.