An efficient method for synthesizing dimethylsulfonio‐34S‐propionate hydrochloride from 34S8

Wirth, Joseph S.; Whitman, William B.

doi:10.1002/jlcr.3696

Cited by 3 publications

(6 citation statements)

References 25 publications

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“…All glassware used in the amino acid extractions and subsequent derivatizations (see below) was acid washed in 3% (vol/vol) HCl for 24 h to remove trace contaminants and then baked at 180°C for 24 h to degrade any remaining organic compounds. Dry HCl was generated as previously described (33). Methanolic HCl was generated by bubbling dry HCl into methanol while stirring.…”

Section: Methodsmentioning

confidence: 99%

“…Synthesis of substrates. Di(methyl-13 C)sulfonio- 34 S-propionate ([ 13 C, 34 S]DMSP) hydrochloride was synthesized as previously described (33). Briefly, 34 S 8 was reduced to Na 2 34 S via a Birch reduction in liquid ammonia (34,35).…”

Section: Methodsmentioning

confidence: 99%

“…The purified [ 13 C, 34 S]DMS was then converted to [ 13 C, 34 S]DMSP hydrochloride via a Michael addition to acrylic acid and washed with CH 2 Cl 2 to remove any excess reactants (37). The isotopic purity of the resulting compound was greater than 98% (33).…”

Section: Methodsmentioning

confidence: 99%

“…The fraction of labeled to unlabeled DMSP in the sterile medium was determined as previously described (33). Briefly, 2 ml of sterile medium was transferred to a 10-ml serum vial.…”

Section: Methodsmentioning

confidence: 99%

“…Calculation of isotopomer enrichments. The relative percent enrichment of each isotopomer was calculated from the relative abundances observed via GC-MS after correction for the natural abundances of 2 H, 13 C, 15 N, 17 O, 18 O, 33 S, 34 S, and 36 S (49) as previously described (50). Briefly, the natural abundance of each mass shift was calculated using a custom R script, and this process was repeated for each of the possible isotopomers for the derivatives of both L-methionine and L-cysteine.…”

Section: Methodsmentioning

confidence: 99%

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Dimethylsulfoniopropionate Sulfur and Methyl Carbon Assimilation inRuegeriaSpecies

Wirth

Wang

Huang

et al. 2020

mBio

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Dimethylsulfoniopropionate (DMSP) is abundant in marine environments and an important source of reduced carbon and sulfur for marine bacteria. While both Ruegeria pomeroyi and Ruegeria lacuscaerulensis possessed genes encoding the DMSP demethylation and cleavage pathways, their responses to DMSP differed. A glucose-fed, chemostat culture of R. pomeroyi consumed 99% of the DMSP even when fed a high concentration of 5 mM. At the same time, cultures released 19% and 7.1% of the DMSP as dimethylsulfide (DMS) and methanethiol, respectively. Under the same conditions, R. lacuscaerulensis consumed only 28% of the DMSP and formed one-third of the amount of gases. To examine the pathways of sulfur and methyl C assimilation, glucose-fed chemostats of both species were fed 100 μM mixtures of unlabeled and doubly labeled [dimethyl-13C, 34S]DMSP. Both species derived nearly all of their sulfur from DMSP despite high sulfate availability. In addition, only 33% and 50% of the methionine was biosynthesized from the direct capture of methanethiol in R. pomeroyi and R. lacuscaerulensis, respectively. The remaining methionine was biosynthesized by the random assembly of free sulfide and methyl-tetrahydrofolate derived from DMSP. Thus, although the two species possessed similar genes encoding DMSP metabolism, their growth responses were very different. IMPORTANCE Dimethylsulfoniopropionate (DMSP) is abundant in marine environments and an important source of reduced carbon and sulfur for marine bacteria. DMSP is the precursor for the majority of atmospheric dimethylsulfide (DMS), a climatically active gas that connects the marine and terrestrial sulfur cycles. Although research into the assimilation of DMSP has been conducted for over 20 years, the fate of DMSP in microbial biomass is not well understood. In particular, the biosynthesis of methionine from DMSP has been a focal point, and it has been widely believed that most methionine was synthesized via the direct capture of methanethiol. Using an isotopic labeling strategy, we have demonstrated that the direct capture of methanethiol is not the primary pathway used for methionine biosynthesis in two Ruegeria species, a genus comprised primarily of globally abundant marine bacteria. Furthermore, although the catabolism of DMSP by these species varied greatly, the anabolic pathways were highly conserved.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

“…The fraction of labeled to unlabeled DMSP in the sterile medium was determined as previously described (33). Briefly, 2 ml of sterile medium was transferred to a 10-ml serum vial.…”

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Dimethylsulfoniopropionate Sulfur and Methyl Carbon Assimilation inRuegeriaSpecies

Wirth

Wang

Huang

et al. 2020

mBio

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Similar but different: Characterization of dddD gene–mediated DMSP metabolism among coral-associated Endozoicomonas

Chiou,

Chan,

et al. 2023

Sci. Adv.

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Endozoicomonas are often predominant bacteria and prominently important in coral health. Their role in dimethylsulfoniopropionate (DMSP) degradation has been a subject of discussion for over a decade. A previous study found that Endozoicomonas degraded DMSP through the dddD pathway. This process releases dimethyl sulfide, which is vital for corals coping with thermal stress. However, little is known about the related gene regulation and metabolic abilities of DMSP metabolism in Endozoicomonadaceae . In this study, we isolated a novel Endozoicomonas DMSP degrader and observed a distinct DMSP metabolic trend in two phylogenetically close dddD -harboring Endozoicomonas species, confirmed genetically by comparative transcriptomic profiling and visualization of the change of DMSP stable isotopes in bacterial cells using nanoscale secondary ion spectrometry. Furthermore, we found that DMSP cleavage enzymes are ubiquitous in coral Endozoicomonas with a preference for having DddD lyase. We speculate that harboring DMSP degrading genes enables Endozoicomonas to successfully colonize various coral species across the globe.

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Similar but different: characterization of dddD gene mediated dimethylsulfoniopropionatemetabolism among Coral-Associated Endozoicomonas

Chiou,

Chan,

et al. 2023

Preprint

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Endozoicomonas, the predominant bacterium associated with corals, is believed to play crucial roles in maintaining coral health. Its role in dimethylsulfoniopropionate (DMSP) degradation has been a subject of discussion for over a decade. A previous study found Endozoicomonas degraded DMSP through dddD pathway. This process releases dimethyl sulfide (DMS), which is vital for corals coping with thermal stress. However, little is known about the related gene regulation and metabolic abilities of DMSP metabolism in Endozoicomonadaceae. In this study, we observed a distinct DMSP metabolic trend in two phylogenetically close dddD -harboring Endozoicomonas species confirming genetically by the comparative transcriptomic profiling and visualizing the change of DMSP stable isotopes in bacterial cell using NanoSIMS. Furthermore, we found that DMSP cleavage enzymes are ubiquitous in coral Endozoicomonas with a preference for possessing DddD lyase. We speculate harboring DMSP degrading genes enables Endozoicomonas to successfully colonize various coral species across the globe. Teaser: Coral-associated Endozoicomonas are widespread DMSP degraders monopolized by the dddD gene, employing various degradation mechanisms.

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An efficient method for synthesizing dimethylsulfonio‐³⁴S‐propionate hydrochloride from ³⁴S₈

Cited by 3 publications

References 25 publications

Dimethylsulfoniopropionate Sulfur and Methyl Carbon Assimilation inRuegeriaSpecies

Dimethylsulfoniopropionate Sulfur and Methyl Carbon Assimilation inRuegeriaSpecies

Similar but different: Characterization of dddD gene–mediated DMSP metabolism among coral-associated Endozoicomonas

Similar but different: characterization of dddD gene mediated dimethylsulfoniopropionatemetabolism among Coral-Associated Endozoicomonas

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