sulfonium compounds


Summary: Sulfur compounds in which the sulfur atom is attached to three organic radicals and an electronegative element or radical.

Top Publications

  1. DeBose J, Lema S, Nevitt G. Dimethylsulfoniopropionate as a foraging cue for reef fishes. Science. 2008;319:1356 pubmed publisher
    ..We present evidence that planktivorous reef fishes will aggregate to experimental deployments of DMSP over coral reef habitats in the wild. ..
  2. Seymour J, Simó R, Ahmed T, Stocker R. Chemoattraction to dimethylsulfoniopropionate throughout the marine microbial food web. Science. 2010;329:342-5 pubmed publisher
  3. Todd J, Curson A, Kirkwood M, Sullivan M, Green R, Johnston A. DddQ, a novel, cupin-containing, dimethylsulfoniopropionate lyase in marine roseobacters and in uncultured marine bacteria. Environ Microbiol. 2011;13:427-38 pubmed publisher
    ..Judged by their frequencies in the Global Ocean Sampling metagenomic databases, DddP and DddQ are relatively abundant among marine bacteria compared with the previously identified DddL and DddD enzymes...
  4. Kiene R, Linn L, Gonzalez J, Moran M, Bruton J. Dimethylsulfoniopropionate and methanethiol are important precursors of methionine and protein-sulfur in marine bacterioplankton. Appl Environ Microbiol. 1999;65:4549-58 pubmed
    ..Our study highlights a remarkable adaptation by marine bacteria: they exploit nanomolar levels of reduced sulfur in apparent preference to sulfate, which is present at 10(6)- to 10(7)-fold higher concentrations. ..
  5. Todd J, Rogers R, Li Y, Wexler M, Bond P, Sun L, et al. Structural and regulatory genes required to make the gas dimethyl sulfide in bacteria. Science. 2007;315:666-9 pubmed
    ..The inferred enzymatic mechanism for DMS liberation involves an initial step in which DMSP is modified by addition of acyl coenzyme A, rather than the immediate release of DMS by a DMSP lyase, the previously suggested mechanism. ..
  6. Amunugama M, Roberts K, Reid G. Mechanisms for the selective gas-phase fragmentation reactions of methionine side chain fixed charge sulfonium ion containing peptides. J Am Soc Mass Spectrom. 2006;17:1631-42 pubmed
    ..As a consequence, the formation of b- or y-type sequence ions are "skipped" at the site of cyclization. Despite this, complete sequence information is still obtained because of the presence of both cyclic products. ..
  7. Todd J, Curson A, Nikolaidou Katsaraidou N, Brearley C, Watmough N, Chan Y, et al. Molecular dissection of bacterial acrylate catabolism--unexpected links with dimethylsulfoniopropionate catabolism and dimethyl sulfide production. Environ Microbiol. 2010;12:327-43 pubmed publisher
    ..This first description of genes involved in acrylate catabolism in any organism shows that the relationship between the catabolic pathways of acrylate and DMSP differs from that which had been suggested in other bacteria...
  8. Curson A, Sullivan M, Todd J, Johnston A. DddY, a periplasmic dimethylsulfoniopropionate lyase found in taxonomically diverse species of Proteobacteria. ISME J. 2011;5:1191-200 pubmed publisher
    ..Although production of DMS and transcription of Alcaligenes dddY are both apparently inducible by pre-growth of cells with DMSP, this substrate must be catabolised to form acrylate, the bona fide coinducer...
  9. Reisch C, Stoudemayer M, Varaljay V, Amster I, Moran M, Whitman W. Novel pathway for assimilation of dimethylsulphoniopropionate widespread in marine bacteria. Nature. 2011;473:208-11 pubmed publisher

More Information


  1. Miller T, Belas R. Dimethylsulfoniopropionate metabolism by Pfiesteria-associated Roseobacter spp. Appl Environ Microbiol. 2004;70:3383-91 pubmed
    ..The diverse metabolism of DMSP by the dinoflagellate-associated Roseobacter spp. offers evidence consistent with a hypothesis that these bacteria benefit from association with DMSP-producing dinoflagellates...
  2. Otte M, Wilson G, Morris J, Moran B. Dimethylsulphoniopropionate (DMSP) and related compounds in higher plants. J Exp Bot. 2004;55:1919-25 pubmed
    ..did not. Ongoing studies with tissue culture of both species have opened up new avenues of research on DMSP in higher plants, ultimately to elucidate the functions of this enigmatic compound...
  3. Howard E, Henriksen J, Buchan A, Reisch C, Bürgmann H, Welsh R, et al. Bacterial taxa that limit sulfur flux from the ocean. Science. 2006;314:649-52 pubmed
    ..One-third of surface ocean bacteria harbor a DMSP demethylase homolog and thereby route a substantial fraction of global marine primary production away from DMS formation and into the marine microbial food web...
  4. Kirkwood M, Le Brun N, Todd J, Johnston A. The dddP gene of Roseovarius nubinhibens encodes a novel lyase that cleaves dimethylsulfoniopropionate into acrylate plus dimethyl sulfide. Microbiology. 2010;156:1900-6 pubmed publisher
    ..However, DddL and DddP have no sequence similarity to each other, so DddP represents a second, wholly different class of DMSP lyase. ..
  5. Rouillon A, Surdin Kerjan Y, Thomas D. Transport of sulfonium compounds. Characterization of the s-adenosylmethionine and s-methylmethionine permeases from the yeast Saccharomyces cerevisiae. J Biol Chem. 1999;274:28096-105 pubmed of sam3Delta and mmp1Delta mutant cells showed that in addition to high affinity permeases, both sulfonium compounds are transported into yeast cells by low affinity transport systems that appear to be carrier-facilitated ..
  6. Yoch D. Dimethylsulfoniopropionate: its sources, role in the marine food web, and biological degradation to dimethylsulfide. Appl Environ Microbiol. 2002;68:5804-15 pubmed
  7. Vila Costa M, Simó R, Harada H, Gasol J, Slezak D, Kiene R. Dimethylsulfoniopropionate uptake by marine phytoplankton. Science. 2006;314:652-4 pubmed
  8. Saló V, Simó R, Vila Costa M, Calbet A. Sulfur assimilation by Oxyrrhis marina feeding on a 35S-DMSP-labelled prey. Environ Microbiol. 2009;11:3063-72 pubmed publisher
    ..This is the first study that provides direct evidence that ingestion of a DMSP-containing prey supplies structural sulfur to a herbivore protist and that quantifies this assimilative supply at one-third of ingested DMSP...
  9. Malmstrom R, Kiene R, Cottrell M, Kirchman D. Contribution of SAR11 bacteria to dissolved dimethylsulfoniopropionate and amino acid uptake in the North Atlantic ocean. Appl Environ Microbiol. 2004;70:4129-35 pubmed
    ..These data suggest that SAR11 bacteria are highly active and play a significant role in C, N, and S cycling in the ocean. ..
  10. Zubkov M, Fuchs B, Archer S, Kiene R, Amann R, Burkill P. Linking the composition of bacterioplankton to rapid turnover of dissolved dimethylsulphoniopropionate in an algal bloom in the North Sea. Environ Microbiol. 2001;3:304-11 pubmed
    ..Our study suggests that single species of bacterioplankton may at times be important in metabolizing DMSP and regulating the generation of DMS in the sea. ..
  11. Spielmeyer A, Gebser B, Pohnert G. Investigations of the uptake of dimethylsulfoniopropionate by phytoplankton. Chembiochem. 2011;12:2276-9 pubmed publisher
    ..This is even true for species that produce no quantifiable amounts of DMSP themselves. ..
  12. Sullivan M, Curson A, Shearer N, Todd J, Green R, Johnston A. Unusual regulation of a leaderless operon involved in the catabolism of dimethylsulfoniopropionate in Rhodobacter sphaeroides. PLoS ONE. 2011;6:e15972 pubmed publisher
    ..sphaeroides acuR-acuI-dddL. ..
  13. Curson A, Todd J, Sullivan M, Johnston A. Catabolism of dimethylsulphoniopropionate: microorganisms, enzymes and genes. Nat Rev Microbiol. 2011;9:849-59 pubmed publisher
  14. Bürgmann H, Howard E, Ye W, Sun F, Sun S, Napierala S, et al. Transcriptional response of Silicibacter pomeroyi DSS-3 to dimethylsulfoniopropionate (DMSP). Environ Microbiol. 2007;9:2742-55 pubmed
    ..DMSP concentration may thus also play a role as a chemical signal, indicating phytoplankton abundance and eliciting a regulatory response aimed at making maximum use of available nutrients...
  15. Ruiz González C, Simó R, Vila Costa M, Sommaruga R, Gasol J. Sunlight modulates the relative importance of heterotrophic bacteria and picophytoplankton in DMSP-sulphur uptake. ISME J. 2012;6:650-9 pubmed publisher
    ..Our results show for the first time a major influence of sunlight in regulating the competition among autotrophic and heterotrophic picoplankton for DMSP uptake at both the daily and seasonal time scales. ..
  16. Howard E, Sun S, Biers E, Moran M. Abundant and diverse bacteria involved in DMSP degradation in marine surface waters. Environ Microbiol. 2008;10:2397-410 pubmed publisher
  17. Sunda W, Kieber D, Kiene R, Huntsman S. An antioxidant function for DMSP and DMS in marine algae. Nature. 2002;418:317-20 pubmed
  18. Raina J, Dinsdale E, Willis B, Bourne D. Do the organic sulfur compounds DMSP and DMS drive coral microbial associations?. Trends Microbiol. 2010;18:101-8 pubmed publisher
  19. Todd J, Curson A, Dupont C, Nicholson P, Johnston A. The dddP gene, encoding a novel enzyme that converts dimethylsulfoniopropionate into dimethyl sulfide, is widespread in ocean metagenomes and marine bacteria and also occurs in some Ascomycete fungi. Environ Microbiol. 2009;11:1376-85 pubmed publisher
    ..The dddP gene is abundant in the bacterial metagenomic sequences in the Global Ocean Sampling Expedition. Thus, dddP has several novel features and is widely dispersed, both taxonomically and geographically...
  20. Moran M, Belas R, Schell M, Gonzalez J, Sun F, Sun S, et al. Ecological genomics of marine Roseobacters. Appl Environ Microbiol. 2007;73:4559-69 pubmed
    ..Genes shared with other cultured marine bacteria include those for utilizing sodium gradients, transport and metabolism of sulfate, and osmoregulation...
  21. Hamilton G, Kanai T, Toste F. Chiral anion-mediated asymmetric ring opening of meso-aziridinium and episulfonium ions. J Am Chem Soc. 2008;130:14984-6 pubmed publisher
    ..The chiral anion concept can also be extended to the related asymmetric opening of meso-episulfonium ions generated by protonation of trichloroacetimidates vicinal to sulfides. ..
  22. Gonzalez J, Kiene R, Moran M. Transformation of sulfur compounds by an abundant lineage of marine bacteria in the alpha-subclass of the class Proteobacteria. Appl Environ Microbiol. 1999;65:3810-9 pubmed
    ..Studies of culturable representatives suggested that the group could mediate a number of steps in the cycling of both organic and inorganic forms of sulfur in marine environments...
  23. Spielmeyer A, Pohnert G. Influence of temperature and elevated carbon dioxide on the production of dimethylsulfoniopropionate and glycine betaine by marine phytoplankton. Mar Environ Res. 2012;73:62-9 pubmed publisher
    ..In diatoms increased CO(2) and temperature led to decreased DMSP concentrations, while rather elevated levels of this metabolite under the influence of these parameters were observed for E. huxleyi...
  24. Todd J, Kirkwood M, Newton Payne S, Johnston A. DddW, a third DMSP lyase in a model Roseobacter marine bacterium, Ruegeria pomeroyi DSS-3. ISME J. 2012;6:223-6 pubmed publisher
    ..In addition to DddW, R. pomeroyi DSS-3 had been shown to have two other, different, DMSP lyases, DddP and DddQ, plus an enzyme that demethylates DMSP, emphasizing the importance of this substrate for this model bacterium...
  25. Tripp H, Kitner J, Schwalbach M, Dacey J, Wilhelm L, Giovannoni S. SAR11 marine bacteria require exogenous reduced sulphur for growth. Nature. 2008;452:741-4 pubmed publisher
    ..P. ubique' relies exclusively on reduced sulphur compounds that originate from other plankton. ..
  26. Todd J, Curson A, Sullivan M, Kirkwood M, Johnston A. The Ruegeria pomeroyi acuI gene has a role in DMSP catabolism and resembles yhdH of E. coli and other bacteria in conferring resistance to acrylate. PLoS ONE. 2012;7:e35947 pubmed publisher
  27. Kavanagh S, Piccinini A, Connon S. The asymmetric synthesis of terminal aziridines by methylene transfer from sulfonium ylides to imines. Org Biomol Chem. 2013;11:3535-40 pubmed publisher
  28. Bae S, Lee J, Shimizu K, Kuwazuka Y. Increase effect of transforming growth factor on eotaxin production by normal cultured dermal fibroblasts stimulated with interleukin-4: inhibitory effect of suplatast tosilate on eotaxin production. Immunol Invest. 2010;39:93-102 pubmed publisher
    ..These results suggest that TGF-beta may regulate skin allergic inflammation by up-regulating eotaxin production in dermal fibroblasts. Suplatast tosilate might suppress this inflammation by inhibiting eotaxin production. ..
  29. Roe C, Hobbs H, Stockman R. Multicomponent synthesis of chiral sulfinimines. Chemistry. 2011;17:2704-8 pubmed publisher
    ..The templates can be synthesized from cheap commodity chemicals in three steps in high yields. Furthermore the template is easily recovered in high yields for recycling. ..
  30. Nagahata T, Kajiwara H, Ohira S, Toda K. Simple field device for measurement of dimethyl sulfide and dimethylsulfoniopropionate in natural waters, based on vapor generation and chemiluminescence detection. Anal Chem. 2013;85:4461-7 pubmed publisher
    ..9956). The developed device is inexpensive, light (5 kg), simple to use, can be applied in the field, and is sensitive enough for fresh- and seawater analysis. ..
  31. Nagakura T, Ogino S, Okubo K, Sato N, Takahashi M, Ishikawa T. Omalizumab is more effective than suplatast tosilate in the treatment of Japanese cedar pollen-induced seasonal allergic rhinitis. Clin Exp Allergy. 2008;38:329-37 pubmed
    ..No anti-omalizumab antibodies were detected. Omalizumab showed significantly greater improvements than suplatast tosilate in the treatment of SAR induced by Japanese cedar pollens. ..
  32. Pinhassi J, Simó R, Gonzalez J, Vila M, Alonso Sáez L, Kiene R, et al. Dimethylsulfoniopropionate turnover is linked to the composition and dynamics of the bacterioplankton assemblage during a microcosm phytoplankton bloom. Appl Environ Microbiol. 2005;71:7650-60 pubmed
  33. Hanashiro K, Tokeshi Y, Nakasone T, Sunagawa M, Nakamura M, Kosugi T. Azelastine and suplatast shorten the distribution half-life of IgE in rats. Mediators Inflamm. 2002;11:61-4 pubmed
    ..These findings suggested that the anti-allergic drugs used in the present study facilitated the excretion of IgE from the circulation in rats. ..
  34. Johnston A, Todd J, Sun L, Nikolaidou Katsaridou M, Curson A, Rogers R. Molecular diversity of bacterial production of the climate-changing gas, dimethyl sulphide, a molecule that impinges on local and global symbioses. J Exp Bot. 2008;59:1059-67 pubmed publisher
  35. Pizzuti M, Minnaard A, Feringa B. Catalytic enantioselective addition of organometallic reagents to N-formylimines using monodentate phosphoramidite ligands. J Org Chem. 2008;73:940-7 pubmed publisher
    ..Under the reaction conditions, partial oxidation of the phosphoramidite ligand to the corresponding phosphoric amide was detected. A preliminary study on the origin and the effect on the catalytic addition reaction is presented. ..
  36. Denolf B, Leemans E, De Kimpe N. Asymmetric synthesis of aziridines by reduction of N-tert-butanesulfinyl alpha-chloro imines. J Org Chem. 2007;72:3211-7 pubmed
    ..All chiral aziridines were obtained as a single diastereomer after recrystallization (overall yield up to 91%) or after flash chromatography. ..
  37. Pei D, Wang Z, Wei S, Zhang Y, Sun J. S-chiral sulfinamides as highly enantioselective organocatalysts. Org Lett. 2006;8:5913-5 pubmed
    ..In the presence of 20 mol % of 2, a broad range of N-aryl ketimines 1 were reduced by trichlorosilane to produce amines 3 in high yield and enantioselectivity. [reaction: see text] ..
  38. Frihed T, Walvoort M, Codée J, van der Marel G, Bols M, Pedersen C. Influence of O6 in mannosylations using benzylidene protected donors: stereoelectronic or conformational effects?. J Org Chem. 2013;78:2191-205 pubmed publisher
    ..One of the intermediates was found to be the ?-oxosulfonium ion. The reactivity of the donor was found to be in between that of the "torsional" disarmed and an armed donor. ..
  39. Tohda Y, Kubo H, Haraguchi R, Iwanaga T, Fukuoka M. Effects of suplatast tosilate (IPD Capsules) on the production of active oxygen by neutrophils and of IL-8 by mononuclear cells. Int Immunopharmacol. 2001;1:1183-7 pubmed
    ..These results suggest the possibility that suplatast tosilate may not only be of benefit for asthma, but may also prevent or control pulmonary fibrosis or emphysema, for which no effective treatment is presently available. ..
  40. Nevitt G. The neuroecology of dimethyl sulfide: a global-climate regulator turned marine infochemical. Integr Comp Biol. 2011;51:819-25 pubmed publisher
  41. Miller T, Hnilicka K, Dziedzic A, Desplats P, Belas R. Chemotaxis of Silicibacter sp. strain TM1040 toward dinoflagellate products. Appl Environ Microbiol. 2004;70:4692-701 pubmed
    ..The implication of Silicibacter sp. strain TM1040 chemotaxis in establishing and maintaining its interaction with P. piscicida is discussed...
  42. Muller K, Schmid E, Kroppenstedt R. Improved identification of mycobacteria by using the microbial identification system in combination with additional trimethylsulfonium hydroxide pyrolysis. J Clin Microbiol. 1998;36:2477-80 pubmed
    ..The combination of conventional library search report with the information of typical MACP patterns yields significantly better discrimination of mycobacterial species than the MIDI method allows. ..
  43. Kocsis M, Nolte K, Rhodes D, Shen T, Gage D, Hanson A. Dimethylsulfoniopropionate biosynthesis in Spartina alterniflora1. Evidence that S-methylmethionine and dimethylsulfoniopropylamine are intermediates. Plant Physiol. 1998;117:273-81 pubmed
    ..This dissimilarity suggests that DMSP synthesis evolved independently in Gramineae and Compositae. ..
  44. Colpaert F, Mangelinckx S, De Kimpe N. Asymmetric synthesis of chiral N-sulfinyl 3-alkyl- and 3-arylpiperidines by ?-alkylation of N-sulfinyl imidates with 1-chloro-3-iodopropane. J Org Chem. 2011;76:234-44 pubmed publisher
    ..Finally, the N-tert-butanesulfinylpiperidines could be efficiently deprotected to enantiomerically pure 3-alkyl- and 3-arylpiperidine hydrochlorides. ..
  45. Davis F, Qiu H, Song M, Gaddiraju N. Vinylaluminum addition to sulfinimines (N-sulfinyl imines). Asymmetric synthesis of anti-alpha-alkyl beta-amino esters. J Org Chem. 2009;74:2798-803 pubmed publisher
    ..Hydrogenation of the aza-MBH adducts with a Rh(I) catalyst affords anti-alpha-substituted N-sulfinyl-beta-amino esters in good yield and high dr (10:1 to 21:1). ..
  46. Yuasa H, Takada J, Hashimoto H. Glycosidase inhibition by cyclic sulfonium compounds. Bioorg Med Chem Lett. 2001;11:1137-9 pubmed
    Inhibitory activities of various cyclic sulfonium compounds including salacinol against several glycosidases were studied and some compounds showed significant inhibition...
  47. Shimizu S, Hattori R, Majima Y, Shimizu T. Th2 cytokine inhibitor suplatast tosilate inhibits antigen-induced mucus hypersecretion in the nasal epithelium of sensitized rats. Ann Otol Rhinol Laryngol. 2009;118:67-72 pubmed
    ..Suplatast tosilate may be useful for the treatment of allergic rhinitis by attenuating the inflammation of the effector phase. ..
  48. Lyon B, Lee P, Bennett J, Ditullio G, Janech M. Proteomic analysis of a sea-ice diatom: salinity acclimation provides new insight into the dimethylsulfoniopropionate production pathway. Plant Physiol. 2011;157:1926-41 pubmed publisher
    ..Proteins from the four enzyme classes of the proposed algal Met transaminase DMSP pathway were among the elevated proteins, supporting our hypothesis and providing candidate genes for future characterization studies. ..
  49. Thiyagarajan M, Gonsalves K, Dean K, Sykes C. Design and performance of EUV resist containing photoacid generator for sub-100 nm lithography. J Nanosci Nanotechnol. 2005;5:1181-3 pubmed
    ..The newly synthesized polymer bound PAG resist, poly (4-hydroxystyrene-co-2-ethyl-2-adamantyl methacrylate-co-PAG) showed sub-50 nm features using EUV Lithography. ..
  50. McGarrigle E, Fritz S, Favereau L, Yar M, Aggarwal V. An efficient synthesis of imidazolinium salts using vinyl sulfonium salts. Org Lett. 2011;13:3060-3 pubmed publisher
    ..Aromatic and aliphatic N-substituents work well. The reaction is proposed to proceed via generation of a vinyl sulfonium salt intermediate from the bromoethylsulfonium triflate. ..
  51. Pathmanaban O, Porter J, White I. Dogger Bank itch in the eastern English Channel: a newly described geographical distribution of an old problem. Clin Exp Dermatol. 2005;30:622-6 pubmed
    ..It has been reported in trawler-men from Le Havre and shell fishermen from Cornwall, and we report it here in a fisherman using fixed nets in the eastern English Channel. ..
  52. Ishido K, Tanabe S, Higuchi K, Sasaki T, Katada C, Azuma M, et al. Eosinophilic gastroenteritis associated with giant folds. Dig Endosc. 2010;22:312-5 pubmed publisher
    ..Because the leukocyte and eosinophil counts continued to increase, the patient was given suplatast, an anti-allergic agent. The symptoms and hematological values improved promptly. The patient recovered uneventfully, with no recurrence. ..
  53. Blackburn M, Smith R, Carson J, Sibley C. The heparin-binding site of antithrombin III. Identification of a critical tryptophan in the amino acid sequence. J Biol Chem. 1984;259:939-41 pubmed
    ..The site of labeling corresponds to Trp 49, which is located within the disulfide-stabilized loops near the NH2-terminal end of the antithrombin III molecule. ..