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{{Chembox |
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{{Chembox |
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| Watchedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 431382949 |
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| verifiedrevid = 438566750 |
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| ImageFile = 2,6-Pyridinedicarbothioicacid.svg |
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| ImageFile = 2,6-Pyridinedicarbothioicacid.svg |
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| ImageSize = |
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| ImageSize = |
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| ImageAlt = |
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| ImageAlt = Skeletal formula of 2,6-pyridinedicarbothioic acid |
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| IUPACName = 2,6-pyridinedicarbothioic acid |
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| ImageFile1 = 2,6-Pyridinedicarbothioic acid 3D ball.png |
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| ImageSize1 = 220 |
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| ImageAlt1 = Ball-and-stick model of the 2,6-pyridinedicarbothioic acid molecule |
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| IUPACName = 2,6-Pyridinedicarbothioic acid |
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| PIN = Pyridine-2,6-bis(carbothioic ''S''-acid) |
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| OtherNames = PDTC, dithiopyridinedicarbothioic acid |
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| OtherNames = PDTC, dithiopyridinedicarbothioic acid |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 69945-42-2 |
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| CASNo = 69945-42-2 |
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| PubChem =25202662 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| SMILES = C1=CC(=NC(=C1)C(=O)S)C(=O)S |
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| PubChem = 10214455 |
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| UNII = KJ7K75Z4JS |
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<!--| PubChem =25202662 twice?--> |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| SMILES = C1=CC(=NC(=C1)C(=O)S)C(=O)S |
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| PubChem = 10214455 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 8389947 |
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| ChemSpiderID = 8389947 |
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| SMILES = O=C(S)c1nc(C(=O)S)ccc1 |
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| SMILES1 = O=C(S)c1nc(C(=O)S)ccc1 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI=1S/C7H5NO2S2/c9-6(11)4-2-1-3-5(8-4)7(10)12/h1-3H,(H,9,11)(H,10,12) |
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| StdInChI=1S/C7H5NO2S2/c9-6(11)4-2-1-3-5(8-4)7(10)12/h1-3H,(H,9,11)(H,10,12) |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = SSRIAMRLMUFTNV-UHFFFAOYSA-N |
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| StdInChIKey = SSRIAMRLMUFTNV-UHFFFAOYSA-N |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=7|H=5|O=2|S=2 |
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| C=7 | H=5 | O=2 | S=2 |
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| Appearance =White crystalline solid |
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| Appearance =White crystalline solid |
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| Density = 1.415 g/cm<sup>3</sup> |
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| Density = 1.415 g/cm<sup>3</sup> |
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| MeltingPtCL = 97 |
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| MeltingPtC = 97 to 99 |
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| MeltingPtCH = 99 |
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| BoilingPtC = 404.4 |
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| Solubility = 1000 g/L (5.02 mol/L)}} |
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| BoilingPtC = 404.4 |
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|Section3={{Chembox Hazards |
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| Solubility = 1000 g/L (5.02 mol/L)}} |
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|MainHazards = acidic |
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| Section3 = {{Chembox Hazards |
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|FlashPtC = 198.4}} |
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| MainHazards = acidic |
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| FlashPt = {{convert|198.4|C|F}} |
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| Autoignition = }} |
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}} |
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'''2,6-Pyridinedicarbothioic acid''' (PDTC) is an ] compound that is produced by some bacteria. It functions as a ], a small ] agent with a high affinity for ]. Siderophores are deployed as ] scavengers for ]. Siderophores solubilize compounds by forming strong complexes. PDTC is secreted by the ] ] '']'' and '']''.<ref>{{cite journal | doi = 10.1007/978-3-211-99661-4_1 | title = Microbial Siderophores | year = 2010 | last1 = Budzikiewicz | first1 = Herbert | volume = 92 | pages = 1–75}}</ref> |
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'''2,6-Pyridinedicarbothioic acid''' (PDTC) is an ] compound that is produced by some bacteria. It functions as a , a low molecular weight compound that ]. Siderophores solubilize compounds by forming strong complexes. PDTC is secreted by the ] ] '']'' and '']''.<ref>{{cite book |doi=10.1007/978-3-211-99661-4_1 |year=2010 |last=Budzikiewicz |first=Herbert |title=Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products, Vol. 92 |editor-first=A. Douglas |editor-last=Kinghorn |editor-first2=Heinz |editor-last2=Falk |editor-first3=Junichi |editor-last3=Kobayashi |volume=92 |trans-title=Progress in the Chemistry of Organic Natural Products |chapter=Microbial Siderophores |pages=1–75 |pmid=20198464 |isbn=978-3-211-99660-7}}</ref> |
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==Synthesis and biosynthesis== |
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==Synthesis and biosynthesis== |
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PDTC can be synthesized by treating the pyridine-2,6-dicarboxylic acid (or its diacid dichloride) with H<sub>2</sub>S in dry ]: |
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PDTC can be synthesized in the laboratory by treating the diacid dichloride of ] with H<sub>2</sub>S in ]: |
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:{{chem2|NC5H3(COCl)2 + 2 H2S + 2 C5H5N → + Cl}} |
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:NC<sub>5</sub>H<sub>3</sub>(COOH)<sub>2</sub> + 2 H<sub>2</sub>S → NC<sub>5</sub>H<sub>3</sub>(COSH)<sub>2</sub> + 2 H<sub>2</sub>O |
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This produces an orange 1:1 ] salt of 2,6-pyridinedicarbothioate. Treatment of this salt with acid give PDTC, which can then be extracted with ]. |
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This route produces the ] salt of pyridinium-2,6-dicarbothioate. Treatment of this orange-colored salt with ] gives colorless PDTC, which can then be extracted with ].<ref>{{cite journal |doi=10.1080/03086648308080490 |title=Zur Struktur Eines 1:1-Adduktes von Pyridin-2,6-Dicarbothiosäure und Pyridin |date=1983 |last1=Hildebrand |first1=U. |last2=Ockels |first2=W. |last3=Lex |first3=J. |last4=Budzikiewicz |first4=H. |journal=Phosphorus and Sulfur and the Related Elements |volume=16 |issue=3 |pages=361–364 }}</ref> |
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The biosynthesis of PDTC remains unclear although some insights can be deduced from the genetics.<ref>{{cite journal | doi = 10.1186/1471-2148-2-8 | year = 2002 | last1 = Cortese | first1 = Marc S | last2 = Caplan | first2 = Allan B | last3 = Crawford | first3 = Ronald L | journal = BMC Evolutionary Biology | volume = 2 | pages = 8 | pmid = 11972321 | title = 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) | pmc = 115864}}</ref> It is suggested that ''Pseudomonas stutzeri'' may have acquired at least one of the genes by lateral transfer from ].<ref name = cortese>{{cite journal | doi = 10.1023/A:1015241925322 | year = 2002 | last1 = Cortese | first1 = Marc S. | last2 = Paszczynski | first2 = Andrzej | last3 = Lewis | first3 = Thomas A. | last4 = Sebat | first4 = Jonathan L. | last5 = Borek | first5 = Vladimir | last6 = Crawford | first6 = Ronald L. | journal = BioMetals | volume = 15 | issue = 2 | pages = 103–120 | pmid = 12046919 | title = Metal chelating properties of pyridine-2,6-bis(thiocarboxylic acid) produced by Pseudomonas spp. And the biological activities of the formed complexes}}</ref> In a proposed biosynthetic sequence pyridine-2,6-dicarboxylic acid, a known bacterial metabolite,<ref name = cortese/> is activated as its bis-adenosine monophosphate (AMP) derivative. The sulfur donor and its activation remain uncertain.<ref name = budzi>{{cite journal | doi = 10.1023/A:1024012015127 | year = 2003 | last1 = Budzikiewicz | first1 = H. | journal = Biodegradation | volume = 14 | issue = 2 | pages = 65–72 | pmid = 12877462 | title = Heteroaromatic monothiocarboxylic acids from Pseudomonas spp}}</ref> |
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The biosynthesis of PDTC remains unclear although some insights can be deduced from the genetics.<ref>{{cite journal | doi = 10.1186/1471-2148-2-8 | year = 2002 | last1 = Cortese | first1 = Marc S | last2 = Caplan | first2 = Allan B | last3 = Crawford | first3 = Ronald L | journal = BMC Evolutionary Biology | volume = 2 | pages = 8 | pmid = 11972321 | title = 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) | pmc = 115864 | doi-access = free }}</ref> It is suggested that ''Pseudomonas stutzeri'' may have acquired at least one of the genes by lateral transfer from ].<ref name = cortese>{{cite journal | doi = 10.1023/A:1015241925322 | year = 2002 | last1 = Cortese | first1 = Marc S. | last2 = Paszczynski | first2 = Andrzej | last3 = Lewis | first3 = Thomas A. | last4 = Sebat | first4 = Jonathan L. | last5 = Borek | first5 = Vladimir | last6 = Crawford | first6 = Ronald L. | journal = BioMetals | volume = 15 | issue = 2 | pages = 103–120 | pmid = 12046919 | title = Metal chelating properties of pyridine-2,6-bis(thiocarboxylic acid) produced by ''Pseudomonas'' spp. And the biological activities of the formed complexes| s2cid = 5545637 }}</ref> In a proposed biosynthetic sequence pyridine-2,6-dicarboxylic acid, a known bacterial metabolite,<ref name = cortese/> is activated as its bis-adenosine monophosphate (AMP) derivative. The sulfur donor and its activation remain uncertain.<ref name = budzi>{{cite journal | doi = 10.1023/A:1024012015127 | year = 2003 | last1 = Budzikiewicz | first1 = H. | journal = Biodegradation | volume = 14 | issue = 2 | pages = 65–72 | pmid = 12877462 | title = Heteroaromatic monothiocarboxylic acids from ''Pseudomonas'' spp| s2cid = 29898226 }}</ref> |
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==Coordination chemistry== |
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==Coordination chemistry== |
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] |
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PDTC binds to both Fe<sup>2+</sup> and Fe<sup>3+</sup>. The ferric complex is brown, whereas the ferrous complex is blue. In the presence of air, the ferrous complex oxidizes to the ferric compound.{{cn|date=May 2011}} It is iron selective<ref name = cortese/> 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.<ref name = budzi/> |
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PDTC binds to both Fe<sup>2+</sup> and Fe<sup>3+</sup>. The ferric complex is brown, whereas the ferrous complex is blue. In the presence of air, the ferrous complex oxidizes to the ferric compound.<ref>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}}</ref> It is iron selective<ref name = cortese/> 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.<ref name = budzi/> |
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== See also == |
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== See also == |
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{{DEFAULTSORT:Pyridinedicarbothioic acid, 2,6-}} |
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{{DEFAULTSORT:Pyridinedicarbothioic acid, 2,6-}} |
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