{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,2]],"date-time":"2026-09-02T13:19:19Z","timestamp":1788355159224,"version":"build-2803163510"},"reference-count":58,"publisher":"American Chemical Society (ACS)","issue":"27","license":[{"start":{"date-parts":[[2019,12,16]],"date-time":"2019-12-16T00:00:00Z","timestamp":1576454400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/pubs.acs.org\/page\/policy\/authorchoice_termsofuse.html"}],"funder":[{"DOI":"10.13039\/100000152","name":"Division of Molecular and Cellular Biosciences","doi-asserted-by":"publisher","award":["MCB1120346"],"award-info":[{"award-number":["MCB1120346"]}],"id":[{"id":"10.13039\/100000152","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2019,12,31]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>The anaerobic oxidation of methane (AOM) mitigates the flux of methane from marine sediments into the water column. AOM is performed by anaerobic methanotrophic archaea (ANME) that reverse the methanogenesis pathway and partner bacteria that utilize the released reducing equivalents for sulfate reduction. Here, we investigated small-molecule extracts from sediment-free thermophilic enrichment cultures of ANME-1 and sulfate-reducing bacteria using ultraperformance liquid chromatography with high-resolution mass spectrometry. During the analysis, we discovered a novel thioquinoxalinol-containing redox molecule as a major component of the chemically derivatized small-molecule pool. This compound contains both a redox active quinoxaline heterocyclic ring and a thiol group. Additionally, the same core structure was identified that contains a sulfate ester on the hydroxyl group, which likely makes the molecule more water soluble. Hydrated versions of both structures were also observed as major compounds in the extracts. On the basis of reactions of model compounds such as quinoxalin-6-ol, the hydrated version appears to be formed from the addition of water to the dehydropyrazine ring followed by an oxidation. These thioquinoxalinol compounds, which represent completely new structures in biochemistry, may be involved in electron transport processes within and\/or between ANME-1 and sulfate-reducing bacteria, may serve protective roles by reacting with toxic compounds such as hydrogen sulfide, or may transport sulfate as a sulfate ester into the sulfate-reducing bacteria.<\/jats:p>","DOI":"10.1021\/acsomega.9b03450","type":"journal-article","created":{"date-parts":[[2019,12,16]],"date-time":"2019-12-16T13:55:36Z","timestamp":1576504536000},"page":"22613-22622","source":"Crossref","is-referenced-by-count":3,"title":["Identification\nof a Redox Active Thioquinoxalinol\nSulfate Compound Produced by an Anaerobic Methane-Oxidizing Microbial\nConsortium"],"prefix":"10.1021","volume":"4","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-9105-7445","authenticated-orcid":true,"given":"Robert H.","family":"White","sequence":"first","affiliation":[{"name":"Virginia Polytechnic Institute and State University , , , ,","place":["Blacksburg, Virginia, United States, 24061"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kylie D.","family":"Allen","sequence":"additional","affiliation":[{"name":"Virginia Polytechnic Institute and State University , , , ,","place":["Blacksburg, Virginia, United States, 24061"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Gunter","family":"Wegener","sequence":"additional","affiliation":[{"name":"Center for Marine Environmental Sciences , , ,","place":["Bremen, Germany, 28359"]},{"name":"University Bremen , , ,","place":["Bremen, Germany, 28359"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2019,12,16]]},"reference":[{"key":"2026090208392340200_cit1","doi-asserted-by":"publisher","first-page":"457","DOI":"10.1016\/j.tibs.2017.02.005","article-title":"Flavins as Covalent Catalysts: New\nMechanisms Emerge","volume":"42","author":"Piano","year":"2017","journal-title":"Trends Biochem. Sci."},{"key":"2026090208392340200_cit2","doi-asserted-by":"publisher","first-page":"333","DOI":"10.1146\/annurev.micro.55.1.333","article-title":"Novel thiols\nof prokaryotes","volume":"55","author":"Fahey","year":"2001","journal-title":"Annu. Rev. Microbiol."},{"key":"2026090208392340200_cit3","doi-asserted-by":"publisher","first-page":"6403","DOI":"10.1128\/aem.02202-14","article-title":"Discovery\nof multiple modified F430 coenzymes in methanogens and\nanaerobic methanotrophic archaea\nsuggests possible new roles for F430 in nature","volume":"80","author":"Allen","year":"2014","journal-title":"Appl. Environ. Microbiol."},{"key":"2026090208392340200_cit4","doi-asserted-by":"publisher","DOI":"10.1128\/mmbr.00074-18","article-title":"Physiology and Distribution of Archaeal\nMethanotrophs That Couple Anaerobic Oxidation of Methane with Sulfate\nReduction","volume":"83","author":"Bhattarai","year":"2019","journal-title":"Microbiol. Mol. Biol. Rev."},{"key":"2026090208392340200_cit5","doi-asserted-by":"publisher","first-page":"296","DOI":"10.1046\/j.1462-2920.2002.00299.x","article-title":"In vitro demonstration\nof anaerobic oxidation of methane coupled to sulphate reduction in\nsediment from a marine gas hydrate area","volume":"4","author":"Nauhaus","year":"2002","journal-title":"Environ.\nMicrobiol."},{"key":"2026090208392340200_cit6","doi-asserted-by":"publisher","first-page":"98","DOI":"10.1111\/j.1462-2920.2004.00669.x","article-title":"Environmental regulation\nof the anaerobic oxidation of methane: a comparison of ANME-I and\nANME-II communities","volume":"7","author":"Nauhaus","year":"2005","journal-title":"Environ. Microbiol."},{"key":"2026090208392340200_cit7","doi-asserted-by":"publisher","first-page":"1654237","DOI":"10.1155\/2017\/1654237","article-title":"Reverse Methanogenesis\nand Respiration in Methanotrophic\nArchaea","volume":"2017","author":"Timmers","year":"2017","journal-title":"Archaea"},{"key":"2026090208392340200_cit8","doi-asserted-by":"publisher","first-page":"467","DOI":"10.1128\/aem.71.1.467-479.2005","article-title":"Diversity\nand distribution of methanotrophic archaea at cold seeps","volume":"71","author":"Knittel","year":"2005","journal-title":"Appl. Environ. Microbiol."},{"key":"2026090208392340200_cit9","doi-asserted-by":"publisher","first-page":"422","DOI":"10.1111\/j.1462-2920.2009.02083.x","article-title":"Metagenome and mRNA expression analyses\nof anaerobic methanotrophic archaea of the ANME-1 group","volume":"12","author":"Meyerdierks","year":"2010","journal-title":"Environ. Microbiol."},{"key":"2026090208392340200_cit10","doi-asserted-by":"publisher","first-page":"1651","DOI":"10.1111\/1462-2920.14077","article-title":"Gene expression\nand\nultrastructure of meso- and thermophilic methanotrophic consortia","volume":"20","author":"Krukenberg","year":"2018","journal-title":"Environ. Microbiol."},{"key":"2026090208392340200_cit11","doi-asserted-by":"publisher","first-page":"3073","DOI":"10.1111\/1462-2920.13283","article-title":"Candidatus Desulfofervidus\nauxilii, a hydrogenotrophic sulfate-reducing bacterium involved in\nthe thermophilic anaerobic oxidation of methane","volume":"18","author":"Krukenberg","year":"2016","journal-title":"Environ. Microbiol."},{"key":"2026090208392340200_cit12","doi-asserted-by":"publisher","first-page":"46","DOI":"10.3389\/fmicb.2016.00046","article-title":"Metabolic Capabilities\nof Microorganisms Involved in\nand Associated with the Anaerobic Oxidation of Methane","volume":"7","author":"Wegener","year":"2016","journal-title":"Front. 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Bacteriol."},{"key":"2026090208392340200_cit19","doi-asserted-by":"publisher","first-page":"2080","DOI":"10.1002\/jssc.200700081","article-title":"Analysis of\n4-methyl-piperazine-1-carbodithioic acid 3-cyano-3,3-diphenyl-propyl\nester hydrochloride and its major metabolites in rat plasma and tissues\nby LC-MS\/MS","volume":"30","author":"Jiang","year":"2007","journal-title":"J. Sep. Sci."},{"key":"2026090208392340200_cit20","doi-asserted-by":"publisher","first-page":"283","DOI":"10.1002\/bms.1200150508","article-title":"Determination of boldenone sulfoconjugate\nand related steroid sulfates in equine urine by high-performance liquid\nchromatography\/tandem mass spectrometry","volume":"15","author":"Weidolf","year":"1988","journal-title":"Biomed.\nEnviron. Mass Spectrom."},{"key":"2026090208392340200_cit21","doi-asserted-by":"publisher","first-page":"149","DOI":"10.1016\/j.aca.2016.06.057","article-title":"A liquid chromatography - tandem\nmass spectrometry method to measure a selected panel of uremic retention\nsolutes derived from endogenous and colonic microbial metabolism","volume":"936","author":"de Loor","year":"2016","journal-title":"Anal. Chim. Acta"},{"key":"2026090208392340200_cit22","first-page":"51","article-title":"Chemistry and Solution Conformation of the Pyridine\ncoenzymes","volume-title":"The Pyridine Nucleotide Coenzymes","author":"Oppernheimer","year":"1992"},{"key":"2026090208392340200_cit23","doi-asserted-by":"publisher","first-page":"2259","DOI":"10.1021\/jo00979a012","article-title":"Diquaternary salts. I. Preparation\nand characterization\nof the diquaternary salts of some diazines and diazoles","volume":"37","author":"Curphey","year":"1972","journal-title":"J. Org. Chem."},{"key":"2026090208392340200_cit24","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1016\/j.jelechem.2010.05.020","article-title":"Redox mechanism of lumazine at a glassy carbon electrode","volume":"647","author":"Diculescu","year":"2010","journal-title":"J. Electroanal. Chem."},{"key":"2026090208392340200_cit25","doi-asserted-by":"publisher","first-page":"107","DOI":"10.1006\/abio.1996.0059","article-title":"Quantitation of hydrogen peroxide\nusing tris(2-carboxyethyl)phosphine","volume":"234","author":"Han","year":"1996","journal-title":"Anal. Biochem."},{"key":"2026090208392340200_cit26","first-page":"585","volume-title":"Biochemistry of Quinones","author":"Morton","year":"1965"},{"key":"2026090208392340200_cit27","doi-asserted-by":"publisher","first-page":"184","DOI":"10.1016\/0003-9861(60)90566-x","article-title":"Inhibition\nof spinach chloroplast photosynthetic reactions\nby p-chlorophenyl-1,1-dimethylurea","volume":"90","author":"Jagendorf","year":"1960","journal-title":"Arch. Biochem.\nBiophys."},{"key":"2026090208392340200_cit28","doi-asserted-by":"crossref","first-page":"355","DOI":"10.1016\/S0021-9258(18)76619-2","article-title":"Potentiometric\nstudy of pyocyanine","volume":"91","author":"Friedheim","year":"1931","journal-title":"J. Biol. Chem."},{"key":"2026090208392340200_cit29","doi-asserted-by":"publisher","first-page":"2881","DOI":"10.1021\/ja01163a020","article-title":"Some Quaternary\nSalts of Pyrazine","volume":"72","author":"Bahner","year":"1950","journal-title":"J. Am. Chem. Soc."},{"key":"2026090208392340200_cit30","doi-asserted-by":"publisher","first-page":"3803","DOI":"10.1021\/ja01164a509","article-title":"Some Quaternary Ammonium Salts of\nQuinoxalines","volume":"72","author":"Easley","year":"1950","journal-title":"J. Am. Chem. Soc."},{"key":"2026090208392340200_cit31","doi-asserted-by":"publisher","first-page":"1357","DOI":"10.1039\/p29840001357","article-title":"Flavosemiquinone\nmodel systems. Part 1. 4-Hydro-1-alkylpyrazinium radical cations","author":"Kaim","year":"1984","journal-title":"J. Chem. Soc., Perkin Trans. 2"},{"key":"2026090208392340200_cit32","doi-asserted-by":"publisher","first-page":"1767","DOI":"10.1039\/p29840001767","article-title":"Flavosemiquinone\nmodel systems. Part 2. Methyl-substituted quinoxaline radical ions","author":"Kaim","year":"1984","journal-title":"J. Chem. Soc., Perkin Trans. 2"},{"key":"2026090208392340200_cit33","doi-asserted-by":"crossref","first-page":"551","DOI":"10.1016\/S0021-9258(18)65920-4","article-title":"Studies\non the terminal electron transport system.\nI. Succinic dehydrogenase","volume":"217","author":"Green","year":"1955","journal-title":"J. Biol. Chem."},{"key":"2026090208392340200_cit34","doi-asserted-by":"publisher","first-page":"339","DOI":"10.1366\/000370270774371642","article-title":"Optical Spectra\nof Phenazine, 5,10-Dihydrophenazine, and the Phenazhydrins","volume":"24","author":"Wheaton","year":"1970","journal-title":"Appl. Spectrosc."},{"key":"2026090208392340200_cit35","doi-asserted-by":"publisher","first-page":"2380","DOI":"10.1021\/es702290a","article-title":"Redox reactions\nof phenazine antibiotics with ferric\n(hydr)oxides and molecular oxygen","volume":"42","author":"Wang","year":"2008","journal-title":"Environ.\nSci. Technol."},{"key":"2026090208392340200_cit36","doi-asserted-by":"publisher","first-page":"7295","DOI":"10.1021\/ja00776a009","article-title":"Electrochemical\nReduction of Pyrazine in Aqueous Media","volume":"94","author":"Klatt","year":"1972","journal-title":"J. Am.\nChem. Soc."},{"key":"2026090208392340200_cit37","doi-asserted-by":"publisher","first-page":"1237","DOI":"10.1002\/jhet.5570170618","article-title":"Titanium(III)\nChloride and Electrochemical\nReduction of Pyrazine, Quinoxaline and Triazine Derivatives and of\nTheir Salts","volume":"17","author":"Armand","year":"1980","journal-title":"J. Heterocycl. Chem."},{"key":"2026090208392340200_cit38","doi-asserted-by":"publisher","first-page":"190","DOI":"10.1149\/1.2411793","article-title":"Electrochemistry\nand Photopotentials\nof Phenazine in Methanol Solutions","volume":"116","author":"Bailey","year":"1969","journal-title":"J. Electrochem.\nSoc."},{"key":"2026090208392340200_cit39","doi-asserted-by":"publisher","first-page":"1043","DOI":"10.1021\/jo00382a013","article-title":"Reduction\nof heterocycles with nickel-aluminum alloy","volume":"52","author":"Lunn","year":"1987","journal-title":"J. Org. Chem."},{"key":"2026090208392340200_cit40","doi-asserted-by":"publisher","first-page":"2488","DOI":"10.1021\/jo01044a534","article-title":"On the Reduction\nof Quinoxaline","volume":"28","author":"Hamer","year":"1963","journal-title":"J. Org. Chem."},{"key":"2026090208392340200_cit41","doi-asserted-by":"publisher","first-page":"3971","DOI":"10.1139\/v74-593","article-title":"Electrochemical Reduction of Pyrazines\ninto Dihydropyrazines. Preparation of Dihydropyrazines","volume":"52","author":"Armand","year":"1974","journal-title":"Can. J. Chem."},{"key":"2026090208392340200_cit42","doi-asserted-by":"publisher","first-page":"220","DOI":"10.1016\/j.electacta.2018.03.114","article-title":"Comparative\nelectrochemical studies of kinetic and thermodynamic parameters of\nQuinoxaline and Brimonidine redox process","volume":"271","author":"Rupar","year":"2018","journal-title":"Electrochim.\nActa"},{"key":"2026090208392340200_cit43","doi-asserted-by":"publisher","first-page":"2860","DOI":"10.1021\/jo01033a012","article-title":"The Oxidative Cyclization\nof 2,5-Dihydroxyphenylalkylamines\nto 5-Hydroxyindoles and 6-Hydroxyquinolines1","volume":"29","author":"Moore","year":"1964","journal-title":"J. Org. Chem."},{"key":"2026090208392340200_cit44","doi-asserted-by":"publisher","first-page":"6126","DOI":"10.1021\/ja200723n","article-title":"Convergent\nAsymmetric Disproportionation\nReactions: Metal\/Br\u00f8nsted Acid Relay Catalysis for Enantioselective\nReduction of Quinoxalines","volume":"133","author":"Chen","year":"2011","journal-title":"J. Am. Chem. Soc."},{"key":"2026090208392340200_cit45","doi-asserted-by":"publisher","first-page":"137","DOI":"10.1016\/j.orggeochem.2013.01.012","article-title":"Detection of coenzyme F430 in deep sea sediments: A\nkey molecule for biological methanogenesis","volume":"58","author":"Takano","year":"2013","journal-title":"Org. Geochem."},{"key":"2026090208392340200_cit46","doi-asserted-by":"publisher","DOI":"10.1126\/sciadv.aao5682","article-title":"Multi-heme cytochromes provide a\npathway for survival\nin energy-limited environments","volume":"4","author":"Deng","year":"2018","journal-title":"Sci. Adv."},{"key":"2026090208392340200_cit47","doi-asserted-by":"crossref","first-page":"100","DOI":"10.1128\/br.41.1.100-180.1977","article-title":"Energy conservation\nin chemotrophic\nanaerobic bacteria","volume":"41","author":"Thauer","year":"1977","journal-title":"Bacteriol. Rev."},{"key":"2026090208392340200_cit48","doi-asserted-by":"publisher","first-page":"115","DOI":"10.1046\/j.1462-2920.2002.00279.x","article-title":"Reduction of Fe(III)\noxide by methanogens in the presence\nand absence of extracellular quinones","volume":"4","author":"Bond","year":"2002","journal-title":"Environ.\nMicrobiol."},{"key":"2026090208392340200_cit49","doi-asserted-by":"publisher","first-page":"1642","DOI":"10.1038\/s41467-018-04097-9","article-title":"A biochemical framework\nfor anaerobic oxidation of methane driven by Fe(III)-dependent respiration","volume":"9","author":"Yan","year":"2018","journal-title":"Nat. Commun."},{"key":"2026090208392340200_cit50","doi-asserted-by":"publisher","first-page":"181","DOI":"10.1111\/j.1574-6941.2001.tb00768.x","article-title":"Iron metabolism\nin anoxic environments\nat near neutral pH","volume":"34","author":"Straub","year":"2001","journal-title":"FEMS Microbiol. Ecol."},{"key":"2026090208392340200_cit51","doi-asserted-by":"publisher","first-page":"1262","DOI":"10.1016\/j.bbagen.2011.06.024","article-title":"Thioredoxin\nglutathione reductase:\nits role in redox biology and potential as a target for drugs against\nneglected diseases","volume":"1810","author":"Prast-Nielsen","year":"2011","journal-title":"Biochim. Biophys. Acta"},{"key":"2026090208392340200_cit52","article-title":"Gram-negative\nmesophilic sulfate-reducing bacteria","volume-title":"The\nProkaryotes","author":"Widdel","year":"2002","edition":"2"},{"key":"2026090208392340200_cit53","doi-asserted-by":"publisher","first-page":"1310","DOI":"10.1038\/nprot.2018.030","article-title":"Establishing\nanaerobic\nhydrocarbon-degrading enrichment cultures of microorganisms under\nstrictly anoxic conditions","volume":"13","author":"Laso-Pe\u0301rez","year":"2018","journal-title":"Nat. Protoc."},{"key":"2026090208392340200_cit54","doi-asserted-by":"publisher","first-page":"85","DOI":"10.1016\/0076-6879(87)43016-4","article-title":"Determination of low-molecular-weight\nthiols using\nmonobromobimane fluorescent labeling and high-performance liquid chromatography","volume":"143","author":"Fahey","year":"1987","journal-title":"Methods Enzymol."},{"key":"2026090208392340200_cit55","doi-asserted-by":"publisher","first-page":"295","DOI":"10.1016\/s0021-9673(96)00809-6","article-title":"Detection of traces\nof oxidized and reduced sulfur compounds in small samples by combination\nof different high-performance liquid chromatography methods","volume":"760","author":"Rethmeier","year":"1997","journal-title":"J. Chromatogr. A"},{"key":"2026090208392340200_cit56","doi-asserted-by":"publisher","first-page":"fnw217","DOI":"10.1093\/femsle\/fnw217","article-title":"Occurrence and biosynthesis\nof 3-mercaptopropionic\nacid in Methanocaldococcus jannaschii","volume":"363","author":"Allen","year":"2016","journal-title":"FEMS Microbiol. Lett."},{"key":"2026090208392340200_cit57","doi-asserted-by":"publisher","first-page":"1401","DOI":"10.1039\/b912521n","article-title":"Tetra-(tetraalkylammonium)octamolybdate\ncatalysts for selective oxidation\nof sulfides to sulfoxides with hydrogen peroxide","volume":"11","author":"Yang","year":"2009","journal-title":"Green Chem."},{"key":"2026090208392340200_cit58","doi-asserted-by":"publisher","first-page":"3708","DOI":"10.1016\/j.tetlet.2017.08.024","article-title":"Synthesis\nand structure of N-methylated azacalix[4]pyridines and azacalix[1]arene[3]pyridines","volume":"58","author":"Li","year":"2017","journal-title":"Tetrahedron Lett."}],"container-title":["ACS Omega"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acsomega.9b03450","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/acsodf\/article-pdf\/4\/27\/22613\/67748265\/acsomega.9b03450.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/acsodf\/article-pdf\/4\/27\/22613\/67748265\/acsomega.9b03450.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,2]],"date-time":"2026-09-02T12:39:28Z","timestamp":1788352768000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/acsodf\/article\/4\/27\/22613\/605670\/Identification-of-a-Redox-Active-Thioquinoxalinol"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2019,12,16]]},"references-count":58,"journal-issue":{"issue":"27","published-online":{"date-parts":[[2019,12,16]]},"published-print":{"date-parts":[[2019,12,31]]}},"URL":"https:\/\/doi.org\/10.1021\/acsomega.9b03450","relation":{},"ISSN":["2470-1343"],"issn-type":[{"value":"2470-1343","type":"electronic"}],"subject":[],"published":{"date-parts":[[2019,12,16]]}}}