Newly discovered polyamine, 2-hydroxyspermidine, in Pseudomonas acidovorans.
A previously unknown hydroxylated polyamine has been recovered from Pseudomonas acidovorans 29. It has been identified as 2-hydroxyspermidine, N4-(3-aminopropyl)-1,4-diaminobutane-2-ol, by its chromatographic behavior, electrophoretic mobility, and reaction with metaperiodate. It can be synthesized enzymatically from 2-hydroxyputrescine by cell-free preparations from Escherichia coli or P. acidovorans 29 which contain propylamine transferase. It is interesting to note that the naturally occurring compound is the 2-hydroxyspermidine and not the 3-hydroxyspermidine, N1-(3-aminopropyl)-1,4-diaminobutane-2-ol, indicating that the propylamine transferase reacts preferentially with the amine distal to the hydroxyl group. A mixture of 2- and 3-hydroxyspermidines and hydroxyspermine was synthesized by reacting acrylonitrile with 2-hydroxyspermidine and catalytic reduction of the products with hydrogen. N-(gamma-aminopropyl)-beta-alanine, used to help identify the hydroxyspermidines, was synthesized from N-(3-aminopropyl)-3-aminopropanenitrile by hydrolysis with 10% NaOH.
D011549:Pseudomonas / Q000032:analysis*; D011700:Putrescine / Q000031:analogs & derivatives / Q000378:metabolism; D013095:Spermidine / Q000031:analogs & derivatives* / Q000096:biosynthesis / Q000302:isolation & purification; D011436:Spermidine Synthase / Q000378:metabolism
D011436:Spermidine Synthase; D013095:Spermidine; D011700:Putrescine