2,6-Pyridinedicarbothioic acid

changed 438566750 2,6-Pyridinedicarbothioicacid.svg Skeletal formula of 2,6-pyridinedicarbothioic acid 2,6-Pyridinedicarbothioic acid 3D ball.png 220 Ball-and-stick model of the 2,6-pyridinedicarbothioic acid molecule Pyridine-2,6-dicarbothioic acid PDTC, dithiopyridinedicarbothioic acid correct CAS 69945-42-2 correct FDA KJ7K75Z4JS C1=CC(=NC(=C1)C(=O)S)C(=O)S 10214455 correct chemspider 8389947 O=C(S)c1nc(C(=O)S)ccc1 correct chemspider 1S/C7H5NO2S2/c9-6(11)4-2-1-3-5(8-4)7(10)12/h1-3H,(H,9,11)(H,10,12) correct chemspider SSRIAMRLMUFTNV-UHFFFAOYSA-N 7 5 2 2 White crystalline solid 1.415 g/cm3 97 to 99 404.4 1000 g/L (5.02 mol/L) acidic 198.4 2,6-Pyridinedicarbothioic acid (PDTC) is an organosulfur compound that is produced by some bacteria. It functions as a siderophore, 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.10.1007/978-3-211-99661-4_1 2010 Budzikiewicz Herbert Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products, Vol. 92 A. Douglas Kinghorn Heinz Falk Junichi Kobayashi 92 Progress in the Chemistry of Organic Natural Products Microbial Siderophores 1–75 20198464 978-3-211-99660-7 Synthesis and biosynthesis PDTC can be synthesized in the laboratory by treating the diacid dichloride of pyridine-2,6-dicarboxylic with H2S in pyridine: NC5H3(COCl)2 + 2 H2S + 2 C5H5N → [C5H5NH+][HNC5H3(COS)2-] + [C5H5NH]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.10.1080/03086648308080490 Zur Struktur Eines 1:1-Adduktes von Pyridin-2,6-Dicarbothiosäure und Pyridin 1983 Hildebrand U. Ockels W. Lex J. Budzikiewicz H. Phosphorus and Sulfur and the Related Elements 16 3 361–364 The biosynthesis of PDTC remains unclear although some insights can be deduced from the genetics. 10.1186/1471-2148-2-8 2002 Cortese Marc S Caplan Allan B Crawford Ronald L BMC Evolutionary Biology 2 8 11972321 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) 115864 free It is suggested that Pseudomonas stutzeri may have acquired at least one of the genes by lateral transfer from mycobacteria. 10.1023/A:1015241925322 2002 Cortese Marc S. Paszczynski Andrzej Lewis Thomas A. Sebat Jonathan L. Borek Vladimir Crawford Ronald L. BioMetals 15 2 103–120 12046919 Metal chelating properties of pyridine-2,6-bis(thiocarboxylic acid) produced by Pseudomonas spp. And the biological activities of the formed complexes 5545637 In a proposed biosynthetic sequence pyridine-2,6-dicarboxylic acid, a known bacterial metabolite, is activated as its bis-adenosine monophosphate (AMP) derivative. The sulfur donor and its activation remain uncertain. 10.1023/A:1024012015127 2003 Budzikiewicz H. Biodegradation 14 2 65–72 12877462 Heteroaromatic monothiocarboxylic acids from Pseudomonas spp 29898226 Coordination chemistry thumb|Structure of Fe(III) complex with two 2,6-pyridinedicarbothioate ligands.10.1515/znb-1984-1123 Untersuchungen zum Redox-System Bis-(pyridin-2,6-dicarbothioato)-Ferrat(II) /-Ferrat(III) [1] 1984 Hildebrand U. Lex J. Taraz K. Winkler S. Ockels W. Budzikiewicz H. Zeitschrift für Naturforschung B 39 11 1607–1613 94908888 free Color code: yellow = S, blue = N and Fe, gray = C, red = O.|left 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.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. 10.1016/S0040-4039(01)85634-3 It is iron selective 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. See also Dipicolinic acid References Category:Thiocarboxylic acids Category:Disubstituted pyridines