Names | |
---|---|
IUPAC name
2,6-Pyridinedicarbothioic acid
| |
Preferred IUPAC name
Pyridine-2,6-bis(carbothioic S-acid) | |
Other names
PDTC, dithiopyridinedicarbothioic acid
| |
Identifiers | |
3D model (
JSmol)
|
|
ChemSpider | |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
C7H5O2S2 | |
Molar mass | 185.24 g·mol−1 |
Appearance | White crystalline solid |
Density | 1.415 g/cm3 |
Melting point | 97 to 99 °C (207 to 210 °F; 370 to 372 K) |
Boiling point | 404.4 °C (759.9 °F; 677.5 K) |
1000 g/L (5.02 mol/L) | |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards
|
acidic |
Flash point | 198.4 °C (389.1 °F; 471.5 K) |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
2,6-Pyridinedicarbothioic acid (PDTC) is an organosulfur compound that is produced by some bacteria. It functions as a , a low molecular weight compound that scavenges iron. Siderophores solubilize compounds by forming strong complexes. PDTC is secreted by the soil bacteria Pseudomonas stutzeri and Pseudomonas putida. [1]
PDTC can be synthesized in the laboratory by treating the diacid dichloride of pyridine-2,6-dicarboxylic with H2S in pyridine:
This route produces the pyridinium salt of pyridinium-2,6-dicarbothioate. Treatment of this orange-colored salt with sulfuric acid gives colorless PDTC, which can then be extracted with dichloromethane. [2]
The biosynthesis of PDTC remains unclear although some insights can be deduced from the genetics. [3] It is suggested that Pseudomonas stutzeri may have acquired at least one of the genes by lateral transfer from mycobacteria. [4] In a proposed biosynthetic sequence pyridine-2,6-dicarboxylic acid, a known bacterial metabolite, [4] is activated as its bis-adenosine monophosphate (AMP) derivative. The sulfur donor and its activation remain uncertain. [5]
PDTC binds to both Fe2+ and Fe3+. The ferric complex is brown, whereas the ferrous complex is blue. In the presence of air, the ferrous complex oxidizes to the ferric compound. [7] It is iron selective [4] as only the Fe complex is soluble in water. PDTC is produced mainly during the exponential phase of bacterial growth. The conditions at which Pseudomonas produces PDTC is 25 °C, pH=8 and sufficient aeration. [5]
Names | |
---|---|
IUPAC name
2,6-Pyridinedicarbothioic acid
| |
Preferred IUPAC name
Pyridine-2,6-bis(carbothioic S-acid) | |
Other names
PDTC, dithiopyridinedicarbothioic acid
| |
Identifiers | |
3D model (
JSmol)
|
|
ChemSpider | |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
C7H5O2S2 | |
Molar mass | 185.24 g·mol−1 |
Appearance | White crystalline solid |
Density | 1.415 g/cm3 |
Melting point | 97 to 99 °C (207 to 210 °F; 370 to 372 K) |
Boiling point | 404.4 °C (759.9 °F; 677.5 K) |
1000 g/L (5.02 mol/L) | |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards
|
acidic |
Flash point | 198.4 °C (389.1 °F; 471.5 K) |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
2,6-Pyridinedicarbothioic acid (PDTC) is an organosulfur compound that is produced by some bacteria. It functions as a , a low molecular weight compound that scavenges iron. Siderophores solubilize compounds by forming strong complexes. PDTC is secreted by the soil bacteria Pseudomonas stutzeri and Pseudomonas putida. [1]
PDTC can be synthesized in the laboratory by treating the diacid dichloride of pyridine-2,6-dicarboxylic with H2S in pyridine:
This route produces the pyridinium salt of pyridinium-2,6-dicarbothioate. Treatment of this orange-colored salt with sulfuric acid gives colorless PDTC, which can then be extracted with dichloromethane. [2]
The biosynthesis of PDTC remains unclear although some insights can be deduced from the genetics. [3] It is suggested that Pseudomonas stutzeri may have acquired at least one of the genes by lateral transfer from mycobacteria. [4] In a proposed biosynthetic sequence pyridine-2,6-dicarboxylic acid, a known bacterial metabolite, [4] is activated as its bis-adenosine monophosphate (AMP) derivative. The sulfur donor and its activation remain uncertain. [5]
PDTC binds to both Fe2+ and Fe3+. The ferric complex is brown, whereas the ferrous complex is blue. In the presence of air, the ferrous complex oxidizes to the ferric compound. [7] It is iron selective [4] as only the Fe complex is soluble in water. PDTC is produced mainly during the exponential phase of bacterial growth. The conditions at which Pseudomonas produces PDTC is 25 °C, pH=8 and sufficient aeration. [5]