Linked Life Data

11679330

Source:http://linkedlifedata.com/resource/pubmed/id/11679330

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
11
pubmed:dateCreated
2001-10-26
pubmed:abstractText
Several investigations have identified benzothiophene-2,3-dione in the organic solvent extracts of acidified cultures degrading dibenzothiophene via the Kodama pathway. In solution at neutral pH, the 2,3-dione exists as 2-mercaptophenylglyoxylate, which cyclizes upon acidification and is extracted as the 2,3-dione. The fate of these compounds in microbial cultures has never been determined. This study investigated the abiotic reactions of 2-mercaptophenylglyoxylate incubated aerobically in mineral salts medium at neutral pH. Oxidation led to the formation of 2-oxo-2-(2-thiophenyl)ethanoic acid disulfide, formed from two molecules of 2-mercaptophenylglyoxylate. Two sequential abiotic, net losses of both a carbon and an oxygen atom produced two additional disulfides, 2-oxo-2-(2-thiophenyl)ethanoic acid 2-benzoic acid disulfide and 2,2'-dithiosalicylic acid. The methods developed to extract and detect these three disulfides were then used for the analysis of a culture of Pseudomonas sp. strain BT1d grown on dibenzothiophene as its sole carbon and energy source. All three of the disulfides were detected, indicating that 2-mercaptophenylglyoxylate is an important, short-lived intermediate in the breakdown of dibenzothiophene via the Kodama pathway. The disulfides eluded previous investigations because of (i) their high polarity, being dicarboxylic acids; (ii) the need to lower the pH of the aqueous medium to <1 to extract them into an organic solvent such as dichloromethane; (iii) their poor solubility in organic solvents, (iv) their removal from organic extracts of cultures during filtration through the commonly used drying agent anhydrous sodium sulfate; and (v) their high molecular masses (362, 334, and 306 Da) compared to that of dibenzothiophene (184 Da).
pubmed:commentsCorrections
http://linkedlifedata.com/resource/pubmed/commentcorrection/11679330-10446711, http://linkedlifedata.com/resource/pubmed/commentcorrection/11679330-10872075, http://linkedlifedata.com/resource/pubmed/commentcorrection/11679330-11064208, http://linkedlifedata.com/resource/pubmed/commentcorrection/11679330-11157249, http://linkedlifedata.com/resource/pubmed/commentcorrection/11679330-3001166, http://linkedlifedata.com/resource/pubmed/commentcorrection/11679330-3146950, http://linkedlifedata.com/resource/pubmed/commentcorrection/11679330-4004209, http://linkedlifedata.com/resource/pubmed/commentcorrection/11679330-4078222, http://linkedlifedata.com/resource/pubmed/commentcorrection/11679330-4557559, http://linkedlifedata.com/resource/pubmed/commentcorrection/11679330-4601045, http://linkedlifedata.com/resource/pubmed/commentcorrection/11679330-596875, http://linkedlifedata.com/resource/pubmed/commentcorrection/11679330-612708, http://linkedlifedata.com/resource/pubmed/commentcorrection/11679330-647478, http://linkedlifedata.com/resource/pubmed/commentcorrection/11679330-6996929, http://linkedlifedata.com/resource/pubmed/commentcorrection/11679330-8021182, http://linkedlifedata.com/resource/pubmed/commentcorrection/11679330-8782392, http://linkedlifedata.com/resource/pubmed/commentcorrection/11679330-9606911, http://linkedlifedata.com/resource/pubmed/commentcorrection/11679330-9783422
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Nov
pubmed:issn
0099-2240
pubmed:author
pubmed:issnType
Print
pubmed:volume
67
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
5084-93
pubmed:dateRevised
2010-9-14
pubmed:meshHeading
pubmed:year
2001
pubmed:articleTitle
Identification of disulfides from the biodegradation of dibenzothiophene.
pubmed:affiliation
Department of Biological Sciences, University of Alberta, Edmonton, Alberta, Canada T6G 2E9.
pubmed:publicationType
Journal Article, Research Support, Non-U.S. Gov't