N1-aminopropylagmatine, a new polyamine produced as a key intermediate in polyamine biosynthesis of an extreme thermophile, Thermus thermophilus.
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.
Department of Molecular Biology, Tokyo University of Pharmacy and Life Science, Hachioji, Japan.
Mio
M
Ohnuma
Yusuke
Y
Terui
Masatada
M
Tamakoshi
Hidemichi
H
Mitome
Masaru
M
Niitsu
Keijiro
K
Samejima
Etsuko
E
Kawashima
Tairo
T
Oshima
D000376:Agmatine / Q000737:chemistry* / Q000378:metabolism; D000595:Amino Acid Sequence; D001426:Bacterial Proteins / Q000235:genetics / Q000378:metabolism*; D002849:Chromatography, Gas; D002851:Chromatography, High Pressure Liquid; D003546:Cysteine Endopeptidases / Q000235:genetics / Q000378:metabolism*; D004247:DNA / Q000737:chemistry; D004591:Electrophoresis, Polyacrylamide Gel; D004926:Escherichia coli / Q000378:metabolism; D005838:Genotype; D006868:Hydrolysis; D007700:Kinetics; D013058:Mass Spectrometry; D008954:Models, Biological; D008956:Models, Chemical; D008957:Models, Genetic; D008969:Molecular Sequence Data; D009154:Mutation; D009841:Oligonucleotides / Q000737:chemistry; D010957:Plasmids / Q000378:metabolism; D011073:Polyamines / Q000737:chemistry* / Q000378:metabolism*; D017386:Sequence Homology, Amino Acid; D013095:Spermidine / Q000737:chemistry; D011436:Spermidine Synthase / Q000235:genetics / Q000378:metabolism*; D013696:Temperature; D016963:Thermus thermophilus / Q000378:metabolism*; D013997:Time Factors
D001426:Bacterial Proteins; D009841:Oligonucleotides; D011073:Polyamines; D000376:Agmatine; D004247:DNA; D011436:Spermidine Synthase; D003546:Cysteine Endopeptidases; C042477:streptopain; D013095:Spermidine