Document Detail

5:3 Polyfluorinated acid aerobic biotransformation in activated sludge via novel "one-carbon removal pathways"
MedLine Citation:
PMID:  22264858     Owner:  NLM     Status:  Publisher    
The polyfluorinated carboxylic acids 5:3 acid (C(5)F(11)CH(2)CH(2)CO(2)H) and 7:3 acid (C(7)F(15)CH(2)CH(2)CO(2)H) are major products from 6:2 FTOH (C(6)F(13)CH(2)CH(2)OH) and 8:2 FTOH (C(8)F(17)CH(2)CH(2)OH) aerobic biotransformation, respectively. The 5:3 and 7:3 acids were dosed into domestic WWTP activated sludge for 90d to determine their biodegradability. The 7:3 acid aerobic biodegradability was low, only 1.7mol% conversion to perfluoroheptanoic acid (PFHpA), whereas no transformation was observed previously in soil. In stark contrast, 5:3 acid aerobic biodegradability was enhanced 10 times in activated sludge compared to soil. The 5:3 acid was not activated by acyl CoEnzyme A (CoA) synthetase, a key step required for further α- or ß-oxidation. Instead, 5:3 acid was directly converted to 4:3 acid (C(4)F(9)CH(2)CH(2)CO(2)H, 14.2mol%) and 3:3 acid (C(3)F(7)CH(2)CH(2)CO(2)H, 0.9mol%) via "one-carbon removal pathways". The 5:3 acid biotransformation also yielded perfluoropentanoic acid (PFPeA, 5.9mol%) and perfluorobutanoic acid (PFBA, 0.8mol%). This is the first report to identify key biotransformation intermediates which demonstrate novel one-carbon removal pathways with sequential removal of CF(2) groups. Identified biotransformation intermediates (10.2mol% in sum) were 5:3 Uacid, α-OH 5:3 acid, 5:2 acid, and 5:2 Uacid. The 5:2 Uacid and 5:2 acid are novel intermediates identified for the first time which confirm the proposed pathways. In the biodegradation pathways, the genesis of the one carbon removal is CO(2) elimination from α-OH 5:3 acid. These results suggest that there are enzymatic mechanisms available in the environment that can lead to 6:2 FTOH and 5:3 acid mineralization. The dehydrogenation from 5:3 acid to 5:3 Uacid was the rate-limiting enzymatic step for 5:3 acid conversion to 4:3 acid.
Ning Wang; Robert C Buck; Bogdan Szostek; Lisa M Sulecki; Barry W Wolstenholme
Related Documents :
20185228 - Liquid phase nitration of benzene over supported ammonium salt of 12-molybdophosphoric ...
16832508 - Markownikoff and anti-markownikoff hydroamination with palladium catalysts immobilized ...
18844418 - An efficient approach to chiral c8/c9-piperazino-substituted 1,4-benzodiazepin-2-ones a...
14685328 - Preparation of enantiomerically pure pyridyl amino acids from serine.
11160538 - Total fat intake modifies plasma fatty acid composition in humans.
2955838 - Zymograms of kurloff cell acid phosphatases. thin layer isoelectric focusing and native...
Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-1-19
Journal Detail:
Title:  Chemosphere     Volume:  -     ISSN:  1879-1298     ISO Abbreviation:  -     Publication Date:  2012 Jan 
Date Detail:
Created Date:  2012-1-23     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0320657     Medline TA:  Chemosphere     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Copyright Information:
Copyright © 2012 Elsevier Ltd. All rights reserved.
E.I. du Pont De Nemours & Company, Inc., Wilmington, DE, USA.
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

Previous Document:  Evaluation of (68)Ga-labeled tracers for PET imaging of myocardial perfusion in pigs.
Next Document:  Vaporization of heavy metals during thermal treatment of model solid waste in a fluidized bed incine...