Comparative studies on the degradation of guanidino and ureido compounds by Pseudomonas

Abstract

~~The utilization of guanidino and ureido compounds was studied in several Pseudomonas species. Multiple routes of agmatine catabolism were found. All members of the homology group I of Pseudomonas use the initial deamination of agmatine to carbamoylputrescine which is subsequently converted to putrescine. In Pseudomonas indigofera, the catabolism of agmatine can also occur via an initial hydrolysis of the amidino group to putrescine catalyzed by an agmatine amidinohydrolase. A third pathway was found in Pseudomonas cepacia, namely oxidative deamination producing guanidinobutyraldehyde catalyzed by agmatine dehydrogenase, followed by formation of guanidinobutyrate and removal of urea by guanidinobutyrate amidinohydrolase to produce 4-aminobutyrate. Novel amidinohydrolases were characterized in P.putida for the utilization of arcaine and audouine, and in P. cepacia for arcaine, homoarginine and guanidinovalerate. Guanidinovalerate amidinohydrolase was also detected in P. doudorofii Some of these amidinohydrolases accept more than one substrate, e.g. guanidinobutyrate and guanidinovalerate utilization by P. doudorofii and P. cepacia, the catabolism of arcaine and audouine by P. putida, and the degradation of arcaine and homoarginine by P. cepacia.

Diguanidinobutane (Arcaine) Degradation inRhodococcussp. C-x

“…Homologues of DGB were synthesized as described previously.4) Homologues of agmatine were prepared from the DGB homologues with diguanidinobutanase of Pseudomonas putida. 4 ) Carbamoylagmatine (I-guanidino-4-ureidobutane) and carbamoylputrescine were prepared by the methods of Tricot et al 5 ) 3-Guanidinopropionate and 5-guanidinovalerate were prepared as described previously. 14) 3-Guanidinopropionamide and its homologues were prepared by the method of Thoai and Olomucki.…”

“…The synthetic carbamoylputrescine to putrescine and urea by agmatinase (EC 3.5.3.11) in Escherichia coli,26) Klebsiella aerogene,~', 2 7) and Pseudomonas indigofera. 5 ) Agmatine is also degraded to 4-guanidinobutyraldehyde. The reaction in P. cepacia is catalyzed by a dehydrogenase 5 ) and that in a nocardioform Nocardioides simplex is catalyzed by an enzyme that transfers the amino group to pyruvate.…”

Function of the Arginine Oxygenase Pathway in Utilization ofL-Arginine-related Compounds inArthrobacter globiformisandBrevibacterium helvolum

“…4) Similar results have been obtained with P. putida degrading L-arginine or other guanidino compounds. 5) The occurrence of multiple pathways for the degradation of L-arginine has been reported for Bacillus and fluorescent Pseudomonas species. 1) None of these bacteria has been reported to have the oxygenase pathway.…”

“…P. cepacia has been suggested to degrade agmatine to 4-guanidinobutyrate via 4-guanidinobutyraldehyde, which is formed from agmatine by phenazine methosulfate-dependent agmatine dehydrogenase. 5) Gram-positive Streptococcus /aecalis hydrolyses agmatine to carbamoylputrescine, and the latter is then degraded to putrescine and carbamoylphosphate by putrescine carbamoyltransferase. 29 ,30) A. globiformis and B. helvolum, which are also Gram-positive bacteria and probably devoid of arginine decarboxylase, can degrade agmatine to 4-aminobutyrate via carbamoylputrescine, putrescine, and 4-aminobutyraldehyde (Table III).…”

“…Degradation of these compounds in several species of the genus Pseudomonas has been studied and three different pathways of agmatine breakdown have been found. 5) Studies on the mutants of P. putida have found that L-citrulline is degraded to L-glutamate via L-proline after the conversion to L-ornithine, and that the major pathway of L-arginine degradation is the arginine oxidase pathway, which does not participate in the L-citrulline breakdown. 2) Coryneform bacteria are now classified as irregular, nonsporing, Gram-positive rods in Bergey's Manual of Systematic Bacteriology6) and a group of high guanine and cytosine contents of DNA comprise this group of bacteria and actinomycete strains.…”