1,3,5-triazine-2,4,6-triamine phosphate

Biotransformation and kinetics

Administrative data

Endpoint:

biotransformation and kinetics

Type of information:

experimental study

Adequacy of study:

supporting study

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

study well documented, meets generally accepted scientific principles, acceptable for assessment

Remarks:

Appropriate publication. Not according to any guideline.

Cross-reference

Reason / purpose for cross-reference:

reference to other study

Data source

Reference

Reference Type:

publication

Title:

Unnamed

Year:

1982

Materials and methods

Principles of method if other than guideline:

The degradative pathway of melamine by Pseudomonas sp. was examined and the degradation products were identified.

GLP compliance:

not specified

Type of medium:

aquatic

Test material

Test material information

Constituent 1

Reference substance name:

Melamine

EC Number:

203-615-4

EC Name:

Melamine

Cas Number:

108-78-1

Molecular formula:

C3H6N6

IUPAC Name:

1,3,5-triazine-2,4,6-triamine

Test material form:

solid

Results and discussion

Transformation products:

yes

Identity of transformation products

Identity of transformation products 1

No.:

#1

Reference

Reference substance name:

Unnamed

IUPAC name:

4,6-diamino-1,3,5-triazin-2(1H)-one

Inventory number:

InventoryMultipleMappingImpl [inventoryEntryValue=EC 211-455-1]

CAS number:

645-92-1

Identifier:

IUPAC name

Identity:

ammeline

Molecular formula:

C3H5N5O

Molecular weight:

127.105

SMILES notation:

NC1=NC(=NC(=O)N1)N

InChl:

InChI=1/C3H5N5O/c4-1-6-2(5)8-3(9)7-1/h(H5,4,5,6,7,8,9)

Identity of transformation products 2

No.:

#2

Reference

Reference substance name:

Unnamed

IUPAC name:

6-amino-1,3,5-triazine-2,4(1H,3H)-dione

Inventory number:

InventoryMultipleMappingImpl [inventoryEntryValue=EC 211-456-7]

CAS number:

645-93-2

Identifier:

IUPAC name

Identity:

ammelide

Molecular formula:

C3H4N4O2

Molecular weight:

128.089

SMILES notation:

NC1=NC(=O)NC(=O)N1

InChl:

InChI=1/C3H4N4O2/c4-1-5-2(8)7-3(9)6-1/h(H4,4,5,6,7,8,9)

Identity of transformation products 3

No.:

#3

Reference

Reference substance name:

Unnamed

IUPAC name:

1,3,5-triazine-2,4,6-triol

Inventory number:

InventoryMultipleMappingImpl [inventoryEntryValue=EC 203-618-0]

CAS number:

108-80-5

Molecular formula:

C3H3N3O3

Molecular weight:

129.07

Identity of transformation products 4

No.:

#4

Any other information on results incl. tables

The bacterium Pseudomonas sp. strain A grew with melamine, ammeline, ammelide, cyanuric acid or NH4+ as sole source of nitrogen, and each substrate was entirely metabolized. Utilization of ammeline, ammelide, cyanuric acid or NH4+ was concomitant with growth. But with melamine as substrate, a transient intermediate was detected, which was identified as ammeline by three methods.

Enzymes from strain A were separated by chromatography on DEAE-cellulose and four activities were examined.

Melamine was converted stoichiometrically into equimolar amounts of ammeline and NH4+.

Ammeline was converted stoichiometrically into equimolar amounts of ammelide and NH4+, ammelide was identified by four methods.

Ammelide was converted stoichiometrically into equimolar amounts of cyanuric acid and NH4+, cyanuric acid was identified by four methods.

Cyanuric acid was converted by an enzyme preparation into an unidentified product with negligible release of NH4+.

The specific activities of the degradative enzymes (>= 0.3 mkat/kg of protein) were high enough to explain the growth rate of the organism.

The bacterium converted 0.4 mM-melamine anaerobically into 2.3 mM NH4+.

Two other pseudomonas and two strains of Klebsiella pneumoniae were also examined, with similar results.

The degradative pathway of melamine appears to be hydrolytic, and proceeds by three successive deaminations to cyanuric acid, which is further metabolized.