Reutericyclin
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(2R)-4-Acetyl-1-[(E)-dec-2-enoyl]-3-hydroxy-2-(2-methylpropyl)-2H-pyrrol-5-one
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3D model (JSmol)
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PubChem CID
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Reutericyclin is a tetramic acid antibiotic produced by the bacterium Limosilactobacillus reuteri (formerly Lactobacillus reuteri) that has potential use as a food preservative.[1] Reutericyclin is a hydrophobic, negatively charged molecule with the molecular formula C20H31NO4.[1][2]
Reutericyclin disrupts the cell membrane of sensitive bacteria by acting as a proton ionophore.[2] Reutericyclin has a broad spectrum of activity against Gram-positive bacteria, but has no effect on Gram-negative bacteria because the lipopolysaccharide (LPS) in the outer membrane of Gram-negative bacteria prevents access by hydrophobic compounds.[1][2]
Biosynthesis
[edit]Reutericyclin is synthesized by some strains of L. reuteri by a 9-gene cluster, containing a polyketide synthase (PKSs) and a non-ribosomal peptide synthetase (NRPS). [3]
References
[edit]- ^ a b c Gänzle MG (2004). "Reutericyclin: biological activity, mode of action, and potential applications". Applied Microbiology and Biotechnology. 64 (3): 326–332. doi:10.1007/s00253-003-1536-8. PMID 14735324.
- ^ a b c Engevik MA, Versalovic J (2017). "Biochemical Features of Beneficial Microbes: Foundations for Therapeutic Microbiology". Microbiology Spectrum. 5 (5): 3–47. doi:10.1128/microbiolspec.BAD-0012-2016. ISBN 9781555819699. PMC 5873327. PMID 28984235.
- ^ Lin, XB; Lohans, CT; Duar, R; Zheng, J; Vederas, JC; Walter, J; Gänzle, M (March 2015). "Genetic determinants of reutericyclin biosynthesis in Lactobacillus reuteri". Applied and environmental microbiology. 81 (6): 2032–41. doi:10.1128/AEM.03691-14. PMID 25576609.
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