The first low molecular weight antibiotic from lactic acid bacteria: Reutericyclin, a new tetramic acid

Angewandte Chemie - International Edition

Volumn 39, Issue 15, 2000, Pages 2766-2768

  Höltzel, Alexandra ^a   Gänzle, Michael G ^b   Nicholson, Graeme J ^a   Hammes, Walter P ^b   Jung, Günther ^a  

^a UNIVERSITY OF TÜBINGEN   (Germany)

^b UNIVERSITY OF HOHENHEIM   (Germany)

Author keywords

Antibiotics; Lactic acid bacteria; Natural products; Structure elucidation; Tetramic acids

Indexed keywords

ANTIBIOTIC AGENT; REUTERICYCLIN; TETRAMIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ARTICLE; CHEMICAL STRUCTURE; DRUG SYNTHESIS; FERMENTATION; FOOD PRESERVATION; INTESTINE FLORA; LACTIC ACID BACTERIUM; NONHUMAN;

EID: 0040778476     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20000804)39:15<2766::AID-ANIE2766>3.0.CO;2-G     Document Type: Article

References (21)

1. M. G. Gänzle, C. Hertel, W. P. Hammes in Beijerinck Centennial. Microbial physiology and gene regulation (Eds.: W. A. Scheffers, J. P. van Dijken), Delft University Press, 1995, pp. 380-381.
2. G. Böcker, P. Stolz, W. P. Hammes, Getriede Mehl Brot 1995, 49, 370-374.
3. 2O/0.1% TFA solution, A/B = 85/15) was used as a final purification step.
4. C. E. Stickings, Biochem. J. 1959, 72, 332-340.
5. a) H.-D. Stachel, K. K. Harigel, H. Poschenrieder, H. Burghard, J. Heterocycl. Chem. 1980, 17, 1195-1199;
6. 2-pyrroline-4-one as the methanolysis product of 1 is based on the mass spectrum of 4 in which the base peak at m/z 209 originales from a McLafferty rearrangement which would require the carbonyl group at position 4.
7. H. Frank, G. J. Nicholson, E. Bayer, J. Chromatogr. 1978, 167, 187-196.
8. U. Marquardt, D. Schmid, G. Jung, Synlett, in press.
9. 13C NMR spectra: a) P. S. Steyn, P. L. Wessels, Tetrahedron Lett. 1978, 47, 4707-4710; b) M. J. Nolte, P. S. Steyn, P. L. Wessels, J. Chem. Soc. Perkin Trans. 1 1980, 1057-1065.
10. 13C NMR spectra: a) P. S. Steyn, P. L. Wessels, Tetrahedron Lett. 1978, 47, 4707-4710; b) M. J. Nolte, P. S. Steyn, P. L. Wessels, J. Chem. Soc. Perkin Trans. 1 1980, 1057-1065.
11. 3-pyrroline-2-one forms: N. Imamura, K. Adachi, H. Sano, J. Antibiot. 1994, 47, 257-261.
12. 3-pyrroline-2-ones (with the exception of magnesidins A and B).
13. I. A. Casas, W. J. Dobrogosz, Microecol. Ther. 1997, 26, 221-231.
14. a) The optimal conditions with respect to temperature, pH, and substrate supply correspond to the conditions during sourdough fermentations: M. G. Gänzle, PhD. thesis, Universität Hohenheim, 1998;
15. b) additionally, it has been shown that reutericyclin-sensitive strains are inhibited in their growth or killed during cofermentation in sourdough containing L. reuteri LTH2584: W. P. Hammes, J. Walter, unpublished results; M. G. Gänzle, R. Vogel, unpublished results.
16. a) P. A. Vandenbergh, FEMS Microbiol Rev. 1993, 12, 221-337;
17. b) M.-L. Niku-Paavola, A. Laitila, T. Mattila-Sandholm, A. Haikara, J. Appl. Microbiol. 1999, 86, 29-35.
18. a) R. W. Jack, J. R. Tagg, B. Ray, Microbiol. Rev. 1995, 59, 171-200;
19. b) R. W. Jack, F. Götz, G. Jung in Biotechnology. Vol. 7, 2nd edition (Eds.: H. Kleinkauf, H. von Döhren), VCH, Weinheim, 1997, pp. 325-368.
20. a) M.-H. Coconnier, V. Liévin, E. Hemery, A. L. Servin, Appl. Environ. Microbiol. 1998, 64, 4573-4580;
21. b) M.-F. Bernet-Camard, V. Liévin, D. Brassart, J.-R. Neeser, A. L. Servia, S. Hudault, Appl. Environ. Microbiol 1997, 63, 2747-2753.