Reutericyclin

Reutericyclin
Names
	IUPAC name (2R)-4-Acetyl-1-[(E)-dec-2-enoyl]-3-hydroxy-2-(2-methylpropyl)-2H-pyrrol-5-one
Identifiers
CAS Number	303957-69-9;
3D model (JSmol)	Interactive image;
ChemSpider	111251545;
PubChem CID	54696024;
	InChI 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;
	SMILES 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). Infobox references

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

^ ^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). 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.
^ 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.

[pmid14735324-1] 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.

[pmid28984235-2] 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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