tetrakis(3-aminopropyl)ammonium and caldopentamine

Recent research progress on polyamines in extreme thermophiles is reviewed. Extreme thermophiles produce two types of unique polyamines; one is longer polyamines such as caldopentamine and caldohexamine, and the other is branched polyamines such as tetrakis(3-aminopropyl)ammonium. The protein synthesis catalyzed by a cell-free extract of Thermus thermophilus, an extreme thermophile, required the presence of a polyamine and the highest activity was found in the presence of tetrakis(3-aminopropyl)ammonium. In vitro experiments, longer polyamines efficiently stabilized double stranded nucleic acids and a branched polyamine, tetrakis(3-aminropyl)ammonium, stabilized stem-and-loop structures. In T. thermophilus, polyamines are synthesized from arginine by a new metabolic pathway; arginine is converted to agmatine and then agmatine is aminopropylated to N(1)-aminopropylagmatine which is converted to spermidine by an enzyme coded by a gene homologous to speB (a gene for agmatinase). In this new pathway spermidine is not synthesized from putrescine. Reverse genetic studies indicated that the unique polyamines are synthesized from spermidine.

Topics: Adenosylmethionine Decarboxylase; Arginine; Bacterial Proteins; Biogenic Polyamines; Carboxy-Lyases; Hot Temperature; Metabolic Networks and Pathways; Poly U; Polyamines; Quaternary Ammonium Compounds; RNA, Transfer; Spermidine Synthase; Thermus thermophilus; Ureohydrolases

Unusual long polyamines such as caldopentamine and caldohexamine, and branched polyamines such as tetrakis(3-aminopropyl)ammonium and N (4)-aminopropylspermidine were often found in cells of extreme thermophiles and hyperthermophiles belonging to both Bacteria and Archaea domains. Some of these unusual polyamines are essential for life at extreme temperatures. In some cases, the unusual polyamines also exist in cells of nonthermophilic organisms and play important physiological roles under normal conditions. Methods for chromatographic analysis, isolation, and chemical syntheses of unusual polyamines as well as experimental methods for measuring their physiological roles are discussed. Especially, many newly improved methods for chemical syntheses are presented in this article.

Topics: Biochemistry; Biosynthetic Pathways; Chromatography, High Pressure Liquid; Magnetic Resonance Spectroscopy; Nucleic Acids; Plasmids; Polyamines; Protein Biosynthesis; Quaternary Ammonium Compounds; Recombination, Genetic; Spermidine; Spermine; Thermus thermophilus

Polyamines, especially branched polyamines such as tetrakis(3-aminopropyl)ammonium (Taa), stabilize the tertiary structure of RNA molecules. In this study, we examined the polyamine binding site of the HIV-1 dimerization initiation site (DIS) in the kissing-loop dimer by the docking simulation. It was found that Taa binds predominantly to the kissing loop interaction site of DIS.

Topics: Binding Sites; Computer Simulation; Dimerization; HIV-1; Models, Molecular; Nucleic Acid Conformation; Polyamines; Quaternary Ammonium Compounds; RNA, Viral