N1-aminopropylagmatine, a new polyamine produced as a key intermediate in polyamine biosynthesis of an extreme thermophile, Thermus thermophilus

J Biol Chem. 2005 Aug 26;280(34):30073-82. doi: 10.1074/jbc.M413332200. Epub 2005 Jun 27.

Abstract

In the extreme thermophile Thermus thermophilus, a disruption mutant of a gene homologous to speB (coding for agmatinase = agmatine ureohydrolase) accumulated N1-aminopropylagmatine (N8-amidino-1,8-diamino-4-azaoctane, N8-amidinospermidine), a new compound, whereas all other polyamines produced by the wild-type strain were absent from the cells. Double disruption of speB and speE (polyamine aminopropyltransferase) resulted in the disappearance of N1-aminopropylagmatine and the accumulation of agmatine. These results suggested the following. 1) N1-Aminopropylagmatine is produced from agmatine by the action of an enzyme coded by speE. 2) N1-Aminopropylagmatine is a metabolic intermediate in the biosynthesis of unique polyamines found in the thermophile. 3) N1-Aminopropylagmatine is a substrate of the SpeB homolog. They further suggest a new biosynthetic pathway in T. thermophilus, by which polyamines are formed from agmatine via N1-aminopropylagmatine. To confirm our speculation, we purified the expression product of the speB homolog and confirmed that the enzyme hydrolyzes N1-aminopropylagmatine to spermidine but does not act on agmatine.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Agmatine / chemistry*
  • Agmatine / metabolism
  • Amino Acid Sequence
  • Bacterial Proteins / genetics
  • Bacterial Proteins / metabolism*
  • Chromatography, Gas
  • Chromatography, High Pressure Liquid
  • Cysteine Endopeptidases / genetics
  • Cysteine Endopeptidases / metabolism*
  • DNA / chemistry
  • Electrophoresis, Polyacrylamide Gel
  • Escherichia coli / metabolism
  • Genotype
  • Hydrolysis
  • Kinetics
  • Mass Spectrometry
  • Models, Biological
  • Models, Chemical
  • Models, Genetic
  • Molecular Sequence Data
  • Mutation
  • Oligonucleotides / chemistry
  • Plasmids / metabolism
  • Polyamines / chemistry*
  • Polyamines / metabolism*
  • Sequence Homology, Amino Acid
  • Spermidine / chemistry
  • Spermidine Synthase / genetics
  • Spermidine Synthase / metabolism*
  • Temperature
  • Thermus thermophilus / metabolism*
  • Time Factors

Substances

  • Bacterial Proteins
  • Oligonucleotides
  • Polyamines
  • Agmatine
  • DNA
  • Spermidine Synthase
  • Cysteine Endopeptidases
  • streptopain
  • Spermidine

Associated data

  • PDB/1UIR