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Prodigiosin information


Prodigiosin
Names
IUPAC name
4-Methoxy-5-[(Z)-(5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl]-1H,1′H-2,2′-bipyrrole
Identifiers
CAS Number
  • 82-89-3 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:82758 checkY
ChEMBL
  • ChEMBL275787 checkY
ChemSpider
  • 10577755 checkY
MeSH Prodigiosin
PubChem CID
  • 5351169
UNII
  • OL369FU7CJ checkY
InChI
  • InChI=1S/C20H25N3O/c1-4-5-6-8-15-11-16(22-14(15)2)12-19-20(24-3)13-18(23-19)17-9-7-10-21-17/h7,9-13,21,23H,4-6,8H2,1-3H3/b16-12+ checkY
    Key: SZXDNGVQRDTJSD-FOWTUZBSSA-N checkY
  • InChI=1/C20H25N3O/c1-4-5-6-8-15-11-16(22-14(15)2)12-19-20(24-3)13-18(23-19)17-9-7-10-21-17/h7,9-13,21,23H,4-6,8H2,1-3H3/b16-12+
    Key: SZXDNGVQRDTJSD-FOWTUZBSBS
SMILES
  • CCCCCc3cc(=Cc2[nH]c(c1ccc[nH]1)cc2OC)nc3C
Properties
Chemical formula
C20H25N3O
Molar mass 323.440 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Prodigiosin is the red dye produced by many strains of the bacterium Serratia marcescens,[1][2] as well as other Gram-negative, gamma proteobacteria such as Vibrio psychroerythrus and Hahella chejuensis. It is responsible for the pink tint occasionally found in grime that accumulates on porcelain surfaces such as bathtubs, sinks, and toilet bowls. It is in the prodiginine family of compounds which are produced in some Gram-negative gamma proteobacteria, as well as select Gram-positive Actinobacteria (e.g. Streptomyces coelicolor).[3] The name prodigiosin is derived from prodigious (i.e. something marvelous).

  1. ^ Bennett JW, Bentley R (2000). "Seeing red: The story of prodigiosin". Adv Appl Microbiol. Advances in Applied Microbiology. 47: 1–32. doi:10.1016/S0065-2164(00)47000-0. ISBN 9780120026470. PMID 12876793.
  2. ^ Yu, Victor L. (1979). "Serratia marcescens — Historical Perspective and Clinical Review". New England Journal of Medicine. 300 (16): 887–893. doi:10.1056/NEJM197904193001604. PMID 370597.
  3. ^ Williamson NR, Fineran PC, Gristwood T, Leeper FJ, Salmond GP (2006). "The biosynthesis and regulation of bacterial prodiginines". Nature Reviews Microbiology. 4 (12): 887–899. doi:10.1038/nrmicro1531. PMID 17109029. S2CID 11649828.

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Prodigiosin

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Prodigiosin is the red dye produced by many strains of the bacterium Serratia marcescens, as well as other Gram-negative, gamma proteobacteria such as...

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Serratia marcescens

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tripyrrole dye called prodigiosin, it may cause staining of the teeth. The biochemical pathway for the production of prodigiosin by S. marcescens has been...

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C20H25N3O

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amide (LSB) Lysergic acid diethylamide (LSD) Methylisopropyllysergamide Prodigiosin This set index page lists chemical structure articles associated with...

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Pyrrole

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metabolites include PQQ, makaluvamine M, ryanodine, rhazinilam, lamellarin, prodigiosin, myrmicarin, and sceptrin. The syntheses of pyrrole-containing haemin...

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Serratia

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animals. Some members of this genus produce a characteristic red pigment, prodigiosin, and can be distinguished from other members of the order Enterobacterales...

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Prodiginines

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Actinomycetota (e.g. Streptomyces coelicolor). The group is named after prodigiosin (prodiginine) and is biosynthesized through a common set of enzymes....

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Corporal of Bolsena

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Raphael. Because of its red pigmentation, caused by expression of the dye prodigiosin, and its ability to grow on bread, S. marcescens has been proposed as...

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Streptomyces variegatus

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species from the genus of Streptomyces. Streptomyces variegatus produces prodigiosin. List of Streptomyces species LPSN bacterio.net Straininfo of Streptomyces...

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Streptomyces hiroshimensis

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isolated from soil. Streptomyces hiroshimensis produces the red pigment prodigiosin. List of Streptomyces species LPSN bacterio.net Deutsche Sammlung von...

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Colonial morphology

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specimens of Serratia marcescens produce an orange-red pigment called prodigiosin.: 26 : 236  Organisms with swarming motility, like Proteus species, exhibit...

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Streptomyces griseoviridis

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Streptomyces griseoviridis produces etamycin, griseoviridin, bactobolin, prodigiosin R1, actinobolin, and rosophilin. Streptomyces griseoviridis can be used...

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Undecylprodigiosin

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D. D. (1966). "The structure and synthesis of undecylprodigiosin. A prodigiosin analogue from Streptomyces". Chemical Communications (22): 825–826. doi:10...

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Biological pigment

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Bacteria produce pigments such as carotenoids, melanin, violacein, prodigiosin, pyocyanin, actinorhodin, and zeaxanthin. Cyanobacteria produce phycocyanin...

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Biofilm

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marcescens is a Gram-negative bacterium that can produce red pigment called prodigiosin when under certain specific environmental conditions. It is a fairly...

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Violacein

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Van De Sand VF (July 1946). "The Antibiotic Activity of Violacein, Prodigiosin, and Phthiocol". Journal of Bacteriology. 52 (1): 145–146. doi:10.1128/JB...

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Tambjamine

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found to be highly similar to proteins in the Red and Pig pathways from prodigiosin biosynthesis, based on sequence data. The biosynthesis of tambjamine...

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Roseophilin

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Fürstner, A. (2003). "Chemistry and Biology of Roseophilin and the Prodigiosin Alkaloids: A Survey of the Last 2500 Years". Angew. Chem. Int. Ed. 42...

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Millicent Goldschmidt

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"Inhibition by temperature of the terminal step in biosynthesis of prodigiosin". Biochemical and Biophysical Research Communications. 19 (2): 177–181...

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Hydrocarbonoclastic bacteria

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and some small molecules of the cell surface, such as gramicidin S and prodigiosin. All petroleum products are derived from crude oil whose major constituents...

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Transporter Classification Database

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2.B.19 The Calix(4)pyrrole Derivative (C4P) Family 2.B.20 The Prodigiosin (Prodigiosin) Chloride/Bicarbonate Exchanger Family 2.B.21 The ortho-Phenylenediamine-bis-Urea...

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TSUP family

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JS; Salmond, GP; Fineran, PC (March 2011). "PigS and PigP regulate prodigiosin biosynthesis in Serratia via differential control of divergent operons...

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