2,6-Pyridinedicarbothioic acid: Difference between revisions
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'''2,6-Pyridinedicarbothioic acid''' (PDTC) is an [[organosulfur]] compound that is produced by some bacteria. It functions as a [[siderophore]], a small [[chelating]] agent with a high affinity for [[iron]]. Siderophores are deployed as [[ion]] scavengers for [[microbes]]. Siderophores solubilize compounds by forming strong complexes. PDTC is secreted by the [[soil]] [[bacteria]] ''[[Pseudomonas stutzeri]]'' and ''[[Pseudomonas putida]]''.<ref> |
'''2,6-Pyridinedicarbothioic acid''' (PDTC) is an [[organosulfur]] compound that is produced by some bacteria. It functions as a [[siderophore]], a small [[chelating]] agent with a high affinity for [[iron]]. Siderophores are deployed as [[ion]] scavengers for [[microbes]]. Siderophores solubilize compounds by forming strong complexes. PDTC is secreted by the [[soil]] [[bacteria]] ''[[Pseudomonas stutzeri]]'' and ''[[Pseudomonas putida]]''.<ref>{{cite journal | doi = 10.1007/978-3-211-99661-4_1}}</ref> |
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Herbert Budzikiewicz "Microbial Siderophores" Progress in the Chemistry of Organic Natural Products, 2010, Vol. 92, p. 1.{{DOI|10.1007/978-3-211-99661-4_1}}.</ref> |
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==Synthesis and biosynthesis== |
==Synthesis and biosynthesis== |
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Revision as of 18:52, 4 May 2011
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| Names | |
|---|---|
| IUPAC name
2,6-pyridinedicarbothioic acid
| |
| Other names
PDTC, dithiopyridinedicarbothioic acid
| |
| Identifiers | |
PubChem CID
|
|
CompTox Dashboard (EPA)
|
|
| Properties | |
| C7H5O2S2 | |
| Molar mass | 199.25 g/mol |
| Appearance | white crystalline |
| Density | 1.415 g/cm3 |
| Melting point | 97–99°C |
| Boiling point | 404.4°C |
| 1000 g/L (5.02 mol/L) | |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards
|
acidic |
| Flash point | 198.4◦C |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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2,6-Pyridinedicarbothioic acid (PDTC) is an organosulfur compound that is produced by some bacteria. It functions as a siderophore, a small chelating agent with a high affinity for iron. Siderophores are deployed as ion scavengers for microbes. Siderophores solubilize compounds by forming strong complexes. PDTC is secreted by the soil bacteria Pseudomonas stutzeri and Pseudomonas putida.[1]
Synthesis and biosynthesis
PDTC can be synthesized by treating the pyridine-2,6-dicarboxylic acid (or its diacid dichloride) with H2S in dry pyridine:
- NC5H3(COOH)2 + 2 H2S → NC5H3(COSH)2 + 2 H2O
This produces an orange 1:1 pyridinium salt of 2,6-pyridinedicarbothioate. Treatment of this salt with acid give PDTC, which can then be extracted with dichloromethane.
The biosynthesis of PDTC remains unclear although some insights can be deduced from the genetics.[2] It is suggested that Pseudomonas stutzeri may have acquired at least one of the genes by lateral transfer from mycobacteria.[3] In a proposed biosynthetic sequence pyridine-2,6-dicarboxylic acid, a known bacterial metabolite,[3] is activated as its bis-adenosine monophosphate (AMP) derivative. The sulfur donor and its activation remain uncertain.[4]
Coordination chemistry
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.[5] It is iron selective[3] 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.[4]
See also
References
- ^ . doi:10.1007/978-3-211-99661-4_1.
{{cite journal}}: Cite journal requires|journal=(help); Missing or empty|title=(help) - ^ . doi:10.1186/1471-2148-2-8.
{{cite journal}}: Cite journal requires|journal=(help); Missing or empty|title=(help)CS1 maint: unflagged free DOI (link) - ^ a b c . doi:10.1023/A:1015241925322.
{{cite journal}}: Cite journal requires|journal=(help); Missing or empty|title=(help) - ^ a b . doi:10.1023/A:1024012015127.
{{cite journal}}: Cite journal requires|journal=(help); Missing or empty|title=(help) - ^ W. Ockels, A. Rijmer, and H. Budzikiewicz. Tetrahedron Letters. 36: 3341–3342.
{{cite journal}}: Missing or empty|title=(help)CS1 maint: multiple names: authors list (link)