Parvibaculum lavamentivorans DS-1 ^T Degrades Centrally Substituted Congeners of Commercial Linear Alkylbenzenesulfonate to Sulfophenyl Carboxylates and Sulfophenyl Dicarboxylates

Abstract

, C6-, C8-, and C10-SPdC. These were identified by electrospray ionization-mass spectrometry (ESI-MS) after separation by high-pressure liquid chromatography (HPLC). ESI ion-trap MS and ESItime of flight-MS were used to confirm the identities of key intermediates. Different mixtures of congenersobtained by separation of commercial LAS by HPLC were degraded, and the degradative products were compared. If a congener carried the sulfophenyl substituent on the 5, 6, or 7 position, SPdCs were formed as well as SPC, SPC-2H, and SPC؉2C, whereas the substituent on the 2, 3, or 4 position yielded only SPC, SPC-2H, and SPC؉2C. Some 50 products were generated from the 20 LAS congeners: 11 major SPCs, each with an SPC-2H and an SPC؉2C (i.e., 33 SPC and SPC-2H species), and about 17 SPdC species. A large array of compounds, many in low quantities, is thus generated by P. lavamentivorans DS-1 during the degradation of commercial LAS.

Characterization of the Tautomycin Biosynthetic Gene Cluster from Streptomyces spiroverticillatus Unveiling New Insights into Dialkylmaleic Anhydride and Polyketide Biosynthesis

“…Of the remaining orfs, the deduced gene product of ttmG exhibits 50% identity to the carboxymuconolactone decarboxylase Plav_1659 (YP_001412935) from Parvibaculum lavamentivorans DS-1, supporting the assignment of TtmG as a carboxylase responsible for the decarboxylation step (Fig. 3) (49).…”

“…BP-7 (44). Formation of the methyl ketone via decarboxylation of a polyketide intermediate is attributed to the putative decarboxylase TtmG because of its homology to the carboxymuconolactone decarboxylase Plav_1659 from P. lavamentivorans DS-1 (49). It is unclear at present the timing of the TtmG-and TtmKcatalyzed steps, although the precise orchestration and ordering of both tailoring reactions must be determined for future biosynthetic engineering efforts to afford TTM analogs predictably (Fig.…”

The Missing Link in Linear Alkylbenzenesulfonate Surfactant Degradation: 4-Sulfoacetophenone as a Transient Intermediate in the Degradation of 3-(4-Sulfophenyl)Butyrate by Comamonas testosteroni KF-1

“…Recognition that the overall degradation of LAS involved communities of microorganisms developed 10 to 15 years ago (36), when routine high-performance liquid chromatography (HPLC) analysis of LAS and SPC in biological samples became available (16,20). The coupling of HPLC technology to mass spectrometers has allowed the analysis of the transient SPC intermediates to be further improved (e.g., see references 7 and 19), such that we now have a comprehensive picture of some 50 SPC-like products (mostly chiral) formed from commercial LAS by the first-tier organism in an LASdegrading bacterial community (27).…”

“…The first tier of organisms, which is so far represented only by Parvibaculum lavamentivorans DS-1 (6,12,(27)(28)(29), converts all LAS congeners to about 50 SPCs (and related compounds, see below) and cell material derived from the acetyl coenzyme A (acetyl-CoA) released through ␤-oxidation from the alkane moiety. In principle, each LAS congener yields three products that are released by strain DS-1, an SPC, an ␣,␤-unsaturated SPC (SPC-2H), and an SPC from the previous round of ␤-oxidation (SPCϩ2C) ( Fig.…”

Quantificação de alquilbenzeno linear sulfonato em estação de tratamento de efluentes e rios por cromatografia líquida de alta eficiência e extração em fase sólida

“…Esse resultado foi associado ao efeito do impedimento estérico, causado pelo grupo fenilsulfonato, o qual é menor nos isômeros em que ele está mais distante do final da cadeia linear, onde a degradação é iniciada. 35,36 Essa constatação pode ser estendida aos demais homólogos, pois têm a mesma função química, diferindo apenas no número de átomos de carbonos na cadeia linear. Ainda, os isômeros com o grupo fenilsulfonato em uma mesma posição são mais facilmente degradados nos homólogos com cadeias lineares maiores, pois estão mais distantes do final da cadeia.…”