Chemistry:2,6-Pyridinedicarbothioic acid

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2,6-Pyridinedicarbothioic acid
Skeletal formula of 2,6-pyridinedicarbothioic acid
Ball-and-stick model of the 2,6-pyridinedicarbothioic acid molecule
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
UNII
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
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).
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Infobox references
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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]

Synthesis and biosynthesis

PDTC can be synthesized in the laboratory by treating the diacid dichloride of pyridine-2,6-dicarboxylic with H2S in pyridine:

NC
5H
3(COCl)
2 + 2 H
2S + 2 C
5H
5N → [C
5H
5NH+
][HNC
5H
3(COS)−
2] + [C
5H
5NH]Cl

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]

Coordination chemistry

Structure of Fe(III) complex with two 2,6-pyridinedicarbothioate ligands.[6] Color code: yellow = S, blue = N and Fe, gray = C, red = O.

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]

See also

References

  1. ↑ Budzikiewicz, Herbert (2010). "Microbial Siderophores". in Kinghorn, A. Douglas. Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products, Vol. 92. 92. pp. 1–75. doi:10.1007/978-3-211-99661-4_1. ISBN 978-3-211-99660-7. 
  2. ↑ Hildebrand, U.; Ockels, W.; Lex, J.; Budzikiewicz, H. (1983). "Zur Struktur Eines 1:1-Adduktes von Pyridin-2,6-Dicarbothiosäure und Pyridin". Phosphorus and Sulfur and the Related Elements 16 (3): 361–364. doi:10.1080/03086648308080490. 
  3. ↑ Cortese, Marc S; Caplan, Allan B; Crawford, Ronald L (2002). "Structural, functional, and evolutionary analysis of moeZ, a gene encoding an enzyme required for the synthesis of the Pseudomonas metabolite, pyridine-2,6-bis(thiocarboxylic acid)". BMC Evolutionary Biology 2: 8. doi:10.1186/1471-2148-2-8. PMID 11972321. 
  4. ↑ 4.0 4.1 4.2 Cortese, Marc S.; Paszczynski, Andrzej; Lewis, Thomas A.; Sebat, Jonathan L.; Borek, Vladimir; Crawford, Ronald L. (2002). "Metal chelating properties of pyridine-2,6-bis(thiocarboxylic acid) produced by Pseudomonas spp. And the biological activities of the formed complexes". BioMetals 15 (2): 103–120. doi:10.1023/A:1015241925322. PMID 12046919. 
  5. ↑ 5.0 5.1 Budzikiewicz, H. (2003). "Heteroaromatic monothiocarboxylic acids from Pseudomonas spp". Biodegradation 14 (2): 65–72. doi:10.1023/A:1024012015127. PMID 12877462. 
  6. ↑ Hildebrand, U.; Lex, J.; Taraz, K.; Winkler, S.; Ockels, W.; Budzikiewicz, H. (1984). "Untersuchungen zum Redox-System Bis-(pyridin-2,6-dicarbothioato)-Ferrat(II) /-Ferrat(III) [1]". Zeitschrift für Naturforschung B 39 (11): 1607–1613. doi:10.1515/znb-1984-1123. 
  7. ↑ Ockels, W., Roemer, A., Budzikiewicz, H., Korth, H., Pulverer, G., "Bacterial constituents. II. An iron(II) complex of pyridine-2,6-di-(monothiocarboxylic acid) - a novel bacterial metabolic product", Tetrahedron Lett. 1978, 3341. doi:10.1016/S0040-4039(01)85634-3



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