Relationship between osmoprotection and the structure and intracellular accumulation of betaines by Escherichia coli.

Naturally occurring betaines, especially glycine betaine and proline betaine, were accumulated by Escherichia coli from urine. In synthetic hyperosmotic medium, with an homologous series of added betaines, (CH3)3N(+)-(CH2)n-COO-, osmoprotective activity and intracellular accumulation decreased monotonically as n increased from 1 to 5. In contrast, alpha-substituted glycine betaines were accumulated in a similar manner to glycine betaine, but with different osmoprotective activities. Arsenobetaine, with a quaternary arsonium group, was also accumulated but amino acids which can become negatively charged in a chemically basic environment were not.