Metabolism of 2,3-dihydroxypropane-1-sulfonate by marine bacteria

Celik, Ersin; Maczka, Michael; Bergen, Nils; Schulz, Stefan; Dickschat, Jeroen S.

doi:10.1039/c7ob00357a

Cited by 15 publications

(14 citation statements)

References 36 publications

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“…A similar series of γ-lactones spanning from pentan-4-olide ( 14) to dodecan-4olide (20), in addition to 3-methylbutan-4-olide ( 21) and 4-methylhex-5-en-4-olide (22), was detected in strain-specific patterns, with almost all of these compounds present in C. marinus; only C. halophilus did not emit lactones. Furans included furan-2-ylmethanol (23), furfural (24), and 2-acetylfuran (25). Cyclohexanol ( 26) was observed only once in C. marinus, and aromatic compounds included benzyl alcohol (27), benzaldehyde (28) and salicylaldehyde ( 29), acetophenone (30) and o-aminoacetophenone (31), 2-phenylethanol (32), and phenylacetone (33).…”

Section: Headspace Analysismentioning

confidence: 99%

“…It has already been pointed out in the 1970s and 1980s that atmospheric DMS is important for the global sulfur cycle [20] and influences the climate on Earth, known as CLAW hypoth-esis according to the authors' initials (Carlson, Lovelock, Andreae, Warren) [21], which underpins the relevance of this algal-bacterial interaction. Isotopic labeling experiments demonstrated that also in laboratory cultures roseobacter group bacteria efficiently degrade DMSP into sulfur volatiles [22,23], but also from other sulfur sources including 2,3-dihydroxypropane-1-sulfonic acid (DHPS, Scheme 1C) labeling was efficiently incorporated into sulfur volatiles [24,25]. Notably, DHPS is produced in large quantities by the marine diatom Thalassiosira pseudonana [26], and diatoms from this genus live in symbiotic relationship with bacteria of the roseobacter group [27].…”

Section: Introductionmentioning

confidence: 99%

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Identification of volatiles from six marine Celeribacter strains

Chhalodia¹,

Rinkel²,

Konvalinková³

et al. 2021

Beilstein J. Org. Chem.

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The volatiles emitted from six marine Rhodobacteraceae species of the genus Celeribacter were investigated by GC–MS. Besides several known compounds including dimethyl trisulfide and S-methyl methanethiosulfonate, the sulfur-containing compounds ethyl (E)-3-(methylsulfanyl)acrylate and 2-(methyldisulfanyl)benzothiazole were identified and their structures were verified by synthesis. Feeding experiments with [methyl-2H3]methionine, [methyl-13C]methionine and [34S]-3-(dimethylsulfonio)propanoate (DMSP) resulted in the high incorporation into dimethyl trisulfide and S-methyl methanethiosulfonate, and revealed the origin of the methylsulfanyl group of 2-(methyldisulfanyl)benzothiazole from methionine or DMSP, while the biosynthetic origin of the benzothiazol-2-ylsulfanyl portion could not be traced. The heterocyclic moiety of this compound is likely of anthropogenic origin, because 2-mercaptobenzothiazole is used in the sulfur vulcanization of rubber. Also in none of the feeding experiments incorporation into ethyl (E)-3-(methylsulfanyl)acrylate could be observed, questioning its bacterial origin. Our results demonstrate that the Celeribacter strains are capable of methionine and DMSP degradation to widespread sulfur volatiles, but the analysis of trace compounds in natural samples must be taken with care.

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Section: Headspace Analysismentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Identification of volatiles from six marine Celeribacter strains

Chhalodia¹,

Rinkel²,

Konvalinková³

et al. 2021

Beilstein J. Org. Chem.

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“…8 DHPS is the substrate for a range of bacterial biomineralization processes that cleave the carbon−sulfur bond to liberate inorganic sulfite, 3 sulfate, 9 or sulfide 10 or that lead to assorted secondary metabolites. 11 For instance, the Desulfovibrio sp. strain DF1 from anaerobic sewage sludge converts DHPS to hydrogen sulfide, 10 while Roseobacter in marine environments convert DHPS to bisulfite.…”

Section: ■ Introductionmentioning

confidence: 99%

Dynamic Structural Changes Accompany the Production of Dihydroxypropanesulfonate by Sulfolactaldehyde Reductase

et al. 2020

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2,3-Dihydroxypropanesulfonate (DHPS) is a major sulfur species in the biosphere. One important route for the production of DHPS is sulfoglycolytic catabolism of sulfoquinovose (SQ) through the Embden-Meyerhof-Parnas (sulfo-EMP) pathway. SQ is a sulfonated carbohydrate present in plant and cyanobacterial sulfolipids (sulfoquinovosyl diacylglyceride and its metabolites) and is biosynthesised globally at a rate of around 10 billion tonnes per annum. The final step in the bacterial sulfo-EMP pathway involves reduction of sulfolactaldehyde (SLA) to DHPS, catalysed by an NADH-dependent SLA reductase. Based on conserved sequence motifs, we assign SLA reductase to the β-hydroxyacid dehydrogenase (β-HAD) family, an example of a β-HAD enzyme that acts on a sulfonic acid substrate, rather than a carboxylic acid. We report crystal structures of the SLA reductase YihU from E. coli K-12 in its apo and cofactor-bound states, as well as a ternary complex YihU•NADH•DHPS with the cofactor and product bound in the active site. Conformational flexibility observed in these structures, combined with kinetic studies, confirm a sequential mechanism and provide evidence for dynamic domain movements that occur during catalysis. The ternary complex structure reveals a conserved sulfonate pocket in SLA reductase that recognises the sulfonate oxygens through hydrogen bonding to Asn174, Ser178, and the backbone amide of Arg123, along with an ordered water molecule. This triad of residues distinguishes these enzymes from classical β-HADs that act on carboxylate substrates. A comparison of YihU crystal structures with close structural homologues within the β-HAD family highlights key differences in the overall domain organization and identifies a peptide sequence that is predictive of SLA reductase activity.

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“…It is present in up to millimolar intracellular concentrations in eukaryotic marine phytoplankton, including the highly abundant diatoms (2,8), which are estimated to contribute ∼20% of the total global primary production (9). These phytoplankton use sulfate, present at ∼30 mM levels in seawater to synthesize a variety of organosulfur compounds including DHPS and sulfoquinovose, Secretion or cell lysis makes these compounds available for degradation by marine heterotrophic bacteria, accounting for a large component of the flux of organic carbon in the surface oceans (8,10).…”

mentioning

confidence: 99%

Two radical-dependent mechanisms for anaerobic degradation of the globally abundant organosulfur compound dihydroxypropanesulfonate

Liu

Wei

Lin

et al. 2020

Proc. Natl. Acad. Sci. U.S.A.

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2(S)-dihydroxypropanesulfonate (DHPS) is a microbial degradation product of 6-deoxy-6-sulfo-d-glucopyranose (sulfoquinovose), a component of plant sulfolipid with an estimated annual production of 1010tons. DHPS is also at millimolar levels in highly abundant marine phytoplankton. Its degradation and sulfur recycling by microbes, thus, play important roles in the biogeochemical sulfur cycle. However, DHPS degradative pathways in the anaerobic biosphere are not well understood. Here, we report the discovery and characterization of two O2-sensitive glycyl radical enzymes that use distinct mechanisms for DHPS degradation. DHPS-sulfolyase (HpsG) in sulfate- and sulfite-reducing bacteria catalyzes C–S cleavage to release sulfite for use as a terminal electron acceptor in respiration, producing H2S. DHPS-dehydratase (HpfG), in fermenting bacteria, catalyzes C–O cleavage to generate 3-sulfopropionaldehyde, subsequently reduced by the NADH-dependent sulfopropionaldehyde reductase (HpfD). Both enzymes are present in bacteria from diverse environments including human gut, suggesting the contribution of enzymatic radical chemistry to sulfur flux in various anaerobic niches.

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Metabolism of 2,3-dihydroxypropane-1-sulfonate by marine bacteria

Cited by 15 publications

References 36 publications

Identification of volatiles from six marine Celeribacter strains

Identification of volatiles from six marine Celeribacter strains

Dynamic Structural Changes Accompany the Production of Dihydroxypropanesulfonate by Sulfolactaldehyde Reductase

Two radical-dependent mechanisms for anaerobic degradation of the globally abundant organosulfur compound dihydroxypropanesulfonate

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