Reutericyclin

Last updated
Reutericyclin
Reutericyclin.svg
Names
IUPAC name
(2R)-4-Acetyl-1-[(E)-dec-2-enoyl]-3-hydroxy-2-(2-methylpropyl)-2H-pyrrol-5-one
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C20H31NO4/c1-5-6-7-8-9-10-11-12-17(23)21-16(13-14(2)3)19(24)18(15(4)22)20(21)25/h11-12,14,16,24H,5-10,13H2,1-4H3/b12-11+
    Key: GNGSBVNLHSNSDF-VAWYXSNFSA-N
  • C(/C=C/CCCCCCC)(=O)N1[C@H](CC(C)C)C(=O)C(C(C)=O)=C1O
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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

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

  1. 1 2 3 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.
  2. 1 2 3 Engevik MA, Versalovic J (2017). Britton RA, Cani PD (eds.). "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.
  3. ↑ 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. Bibcode:2015ApEnM..81.2032L. doi:10.1128/AEM.03691-14. PMC   4345372 . PMID   25576609.
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