5:3 Polyfluorinated acid aerobic biotransformation in activated sludge via novel "one-carbon removal pathways"
Wang, N; Buck, RC; Szostek, B; Sulecki, LM; Wolstenholme, BW
HERO ID
2325379
Reference Type
Journal Article
Year
2012
Language
English
PMID
| HERO ID | 2325379 |
|---|---|
| In Press | No |
| Year | 2012 |
| Title | 5:3 Polyfluorinated acid aerobic biotransformation in activated sludge via novel "one-carbon removal pathways" |
| Authors | Wang, N; Buck, RC; Szostek, B; Sulecki, LM; Wolstenholme, BW |
| Journal | Chemosphere |
| Volume | 87 |
| Issue | 5 |
| Page Numbers | 527-534 |
| Abstract | 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 90 d to determine their biodegradability. The 7:3 acid aerobic biodegradability was low, only 1.7 mol% 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, 14.2 mol%) and 3:3 acid (C(3)F(7)CH(2)CH(2)CO(2)H, 0.9 mol%) via "one-carbon removal pathways". The 5:3 acid biotransformation also yielded perfluoropentanoic acid (PFPeA, 5.9 mol%) and perfluorobutanoic acid (PFBA, 0.8 mol%). 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 (10.2 mol% 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. |
| Doi | 10.1016/j.chemosphere.2011.12.056 |
| Pmid | 22264858 |
| Wosid | WOS:000302524100013 |
| Url | https://www.scopus.com/inward/record.uri?eid=2-s2.0-84857801750&doi=10.1016%2fj.chemosphere.2011.12.056&partnerID=40&md5=a5944e3650d89f56d9b96b8cf2a31f79 |
| Is Certified Translation | No |
| Dupe Override | No |
| Comments | Scopus URL: https://www.scopus.com/inward/record.uri?eid=2-s2.0-84857801750&doi=10.1016%2fj.chemosphere.2011.12.056&partnerID=40&md5=a5944e3650d89f56d9b96b8cf2a31f79 |
| Is Public | Yes |
| Language Text | English |
| Keyword | 5:3 Polyfluorinated acid (5:3 acid); 7:3 Polyfluorinated acid (7:3 acid); Biodegradation; Biotransformation; Fluorotelomer alcohols; Perfluoroalkyl carboxylic acids |