Abstract
Glycine betaine is believed to be the most active naturally occurring osmoprotectant molecule for Escherichia coli and other bacteria. It is a dipolar ion possessing a quaternary ammonimum group and a carboxylic acid group. To examine the molecular requirements for osmoprotective activity, dimethylthetin was compared with glycine betaine. Dimethylthetin is identical to glycine betaine except for substitution of dimethyl sulfonium for the quaternary nitrogen group. Dimethylthetin was found to be about equally as effective as glycine betaine in permitting E. coli to grow in hypertonic NaCl, and both compounds were recovered almost completely from bacterial cells grown in the presence of hypertonic NaCl. 3-Dimethylsulfonioproprionate, an analog of dimethylthetin observed in marine algae, and 3-Dimethylsulfonio-2-methylproprionate were found to be less active. Dimethylthetin may prove useful as a molecular probe to study betaine metabolism and as a model for the development of antibacterial agents.
Full text
PDF
Selected References
These references are in PubMed. This may not be the complete list of references from this article.
- Alphen W. V., Lugtenberg B. Influence of osmolarity of the growth medium on the outer membrane protein pattern of Escherichia coli. J Bacteriol. 1977 Aug;131(2):623–630. doi: 10.1128/jb.131.2.623-630.1977. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Bagnasco S., Balaban R., Fales H. M., Yang Y. M., Burg M. Predominant osmotically active organic solutes in rat and rabbit renal medullas. J Biol Chem. 1986 May 5;261(13):5872–5877. [PubMed] [Google Scholar]
- Chambers S. T., Kunin C. M. Isolation of glycine betaine and proline betaine from human urine. Assessment of their role as osmoprotective agents for bacteria and the kidney. J Clin Invest. 1987 Mar;79(3):731–737. doi: 10.1172/JCI112878. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Chambers S., Kunin C. M. The osmoprotective properties of urine for bacteria: the protective effect of betaine and human urine against low pH and high concentrations of electrolytes, sugars, and urea. J Infect Dis. 1985 Dec;152(6):1308–1316. doi: 10.1093/infdis/152.6.1308. [DOI] [PubMed] [Google Scholar]
- Imhoff J. F., Rodriguez-Valera F. Betaine is the main compatible solute of halophilic eubacteria. J Bacteriol. 1984 Oct;160(1):478–479. doi: 10.1128/jb.160.1.478-479.1984. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Laimins L. A., Rhoads D. B., Altendorf K., Epstein W. Identification of the structural proteins of an ATP-driven potassium transport system in Escherichia coli. Proc Natl Acad Sci U S A. 1978 Jul;75(7):3216–3219. doi: 10.1073/pnas.75.7.3216. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Le Rudulier D., Strom A. R., Dandekar A. M., Smith L. T., Valentine R. C. Molecular biology of osmoregulation. Science. 1984 Jun 8;224(4653):1064–1068. doi: 10.1126/science.224.4653.1064. [DOI] [PubMed] [Google Scholar]
- Lugtenberg B., Peters R., Bernheimer H., Berendsen W. Influence of cultural conditions and mutations on the composition of the outer membrane proteins of Escherichia coli. Mol Gen Genet. 1976 Sep 23;147(3):251–262. doi: 10.1007/BF00582876. [DOI] [PubMed] [Google Scholar]
- Perroud B., Le Rudulier D. Glycine betaine transport in Escherichia coli: osmotic modulation. J Bacteriol. 1985 Jan;161(1):393–401. doi: 10.1128/jb.161.1.393-401.1985. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Rhoads D. B., Waters F. B., Epstein W. Cation transport in Escherichia coli. VIII. Potassium transport mutants. J Gen Physiol. 1976 Mar;67(3):325–341. doi: 10.1085/jgp.67.3.325. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Yancey P. H., Clark M. E., Hand S. C., Bowlus R. D., Somero G. N. Living with water stress: evolution of osmolyte systems. Science. 1982 Sep 24;217(4566):1214–1222. doi: 10.1126/science.7112124. [DOI] [PubMed] [Google Scholar]