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Chemical Compound Review

Sulfonium     sulfanium

Synonyms: sulphonium, sulfur(1+), AGN-PC-0CQBRK, Sulfur cation, CHEBI:29832, ...
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Disease relevance of sulfonium


Psychiatry related information on sulfonium


High impact information on sulfonium


Chemical compound and disease context of sulfonium


Biological context of sulfonium

  • In the assembly, 1-hydroxyl glucosazido- and 1-thio uronic acid donors are combined in a sequential glycosylation protocol using sulfonium triflate activator systems [10].
  • The results of these experiments strongly support a role for Glu47 as an anchor for the sulfonium pole of (S,S)-SAM, and consequently a role as an active site determinant of reaction specificity [11].
  • The types of transformations in which it is involved include decarboxylation, electrophilic addition to any of the three carbons bonded to the central sulfur atom, proton removal at carbons adjacent to the sulfonium, and reductive cleavage to generate 5'-deoxyadenosyl 5'-radical intermediates [12].
  • In addition, incubation of the Met-192 phenacyl sulfonium enzyme at neutral pH causes a smooth irreversible change to the new phenacyl-enzyme as monitored by changes in enzymatic activity, susceptibility to dealkylation using 2-mercaptoethanol, and ultraviolet difference absorption spectral properties [13].
  • Key to success are the formation of its 2,4-disubstituted furan moiety via a palladium-catalyzed alkylation of vinylepoxide 10 derived from sulfonium salt 8 and the use of SEM ethers as the protecting groups for the phenolic OH functions [14].

Anatomical context of sulfonium

  • The sulfonium analogue, however, was much more cytotoxic to HL-60 cells than PAF itself, in the concentration range 0-15 microM; replacement of the acetate group by a benzyl group increased the cytotoxicity to the level of that of the methoxy analogue of PAF [15].
  • Replacement of mouse LM fibroblast choline by a sulfonium analog. Effects on membrane properties as determined by virus probes [16].

Associations of sulfonium with other chemical compounds

  • To duplicate the sulfonium link in myeloperoxidase and to obtain information on its mechanism of formation, we have engineered a methionine residue close to the 2-vinyl group in recombinant pea cytosolic ascorbate peroxidase (rpAPX) by replacement of Ser160 by Met (S160M variant) [17].
  • Transferred nuclear Overhauser effect and rotating-frame Overhauser enhancement NMR spectroscopies are used to probe the conformation of a bicyclic sulfonium ion, which is an analogue of the naturally occurring glycosidase inhibitor castanospermine, bound to the enzyme glucoamylase G2 [18].
  • The methionyl group typically adopts an extended conformation in complexes with enzymes that transfer the methyl group from the sulfonium center, but is more folded in complexes with proteins that do not catalyze reactions involving the sulfur and which can use the sulfonium sulfur solely as a binding site [19].
  • These compounds are 5'-methylethyl(5'adenosyl) sulfonium chloride (MEAS), 5'-methylpropyl-(5'adenosyl)sulfonium chloride (MPAS), and 5'-ethylpropyl(5'-adenosyl)sulfonium chloride (EPAS) They were prepared by reacting an alkyl iodide with the appropriate alkyladenosyl thioether [20].
  • The combined results of these studies have been initially interpreted in terms of a neutral pH, phenacyl bromide modification resulting in formation of a new modified enzyme via the Met-192 sulfonium salt [13].

Gene context of sulfonium

  • Sequence comparisons suggest that the two ester linkages to the heme may also occur in other homologous mammalian peroxidases, but that the sulfonium ion linkage may be a unique feature of myeloperoxidase [21].
  • Synthetic decarboxylated S-adenosyl-L-methionine (dcAdoMet), a mixture of the absolute configuration of S and R at the sulfonium center, was evaluated as a substrate for the measurement of spermidine synthase activity [22].
  • Methylation of glucagon, characterization of the sulfonium derivative, and regeneration of the native covalent structure [23].
  • Treatment of c[alphaZ-Lys-Pro-Aba-(6-CH2-OC6H5)-Glyn], obtained by peptide synthesis in solution, with R2S/TFA simutaneously cleaved the Z protecting group and the phenyl ether function and led to a series of cyclopeptide sulfonium salts [24].
  • The structural features of S-adenosyl-L-methionine (SAM)3 required for optimal binding to a nucleolar 2'-O-methyltransferase were elucidated using various analogs of SAM with modifications of the amino acid, sugar, sulfonium center, and base portions of the molecule [25].

Analytical, diagnostic and therapeutic context of sulfonium


  1. Proofreading and the evolution of a methyl donor function. Cyclization of methionine to S-methyl homocysteine thiolactone by Escherichia coli methionyl-tRNA synthetase. Jakubowski, H. J. Biol. Chem. (1993) [Pubmed]
  2. Chelating agents related to ethylenediamine bis(2-hydroxyphenyl)acetic acid (EDDHA): synthesis, characterization, and equilibrium studies of the free ligands and their Mg2+, Ca2+, Cu2+, and Fe3+ chelates. Yunta, F., García-Marco, S., Lucena, J.J., Gómez-Gallego, M., Alcázar, R., Sierra, M.A. Inorganic chemistry. (2003) [Pubmed]
  3. Inhibition of Clostridium perfringens phospholipase C by ammonium and sulfonium dications. Young, P.R., Synder, W.R., McMahon, R.F. Biochim. Biophys. Acta (1992) [Pubmed]
  4. Behavioral effects of a dimethylsulfonium analog of dopamine after injection into the nucleus accumbens and the striatum. Boldry, R., Chang, Y., Miller, D.D., Uretsky, N.J. Pharmacol. Biochem. Behav. (1986) [Pubmed]
  5. Bioactive conformation of luteinizing hormone-releasing hormone: evidence from a conformationally constrained analog. Freidinger, R.M., Veber, D.F., Perlow, D.S., Brooks, J.R., Saperstein, R. Science (1980) [Pubmed]
  6. Biosynthesis and urinary excretion of methyl sulfonium derivatives of the sulfur mustard analog, 2-chloroethyl ethyl sulfide, and other thioethers. Mozier, N.M., Hoffman, J.L. FASEB J. (1990) [Pubmed]
  7. Interaction between dietary methionine and methyl donor intake on rat liver betaine-homocysteine methyltransferase gene expression and organization of the human gene. Park, E.I., Garrow, T.A. J. Biol. Chem. (1999) [Pubmed]
  8. The sulfonium ion linkage in myeloperoxidase. Direct spectroscopic detection by isotopic labeling and effect of mutation. Kooter, I.M., Moguilevsky, N., Bollen, A., van der Veen, L.A., Otto, C., Dekker, H.L., Wever, R. J. Biol. Chem. (1999) [Pubmed]
  9. The heparin binding site of antithrombin III. Evidence for a critical tryptophan residue. Blackburn, M.N., Sibley, C.C. J. Biol. Chem. (1980) [Pubmed]
  10. A modular strategy toward the synthesis of heparin-like oligosaccharides using monomeric building blocks in a sequential glycosylation strategy. Codée, J.D., Stubba, B., Schiattarella, M., Overkleeft, H.S., van Boeckel, C.A., van Boom, J.H., van der Marel, G.A. J. Am. Chem. Soc. (2005) [Pubmed]
  11. Glutamate 47 in 1-aminocyclopropane-1-carboxylate synthase is a major specificity determinant. McCarthy, D.L., Capitani, G., Feng, L., Gruetter, M.G., Kirsch, J.F. Biochemistry (2001) [Pubmed]
  12. Insight into the polar reactivity of the onium chalcogen analogues of S-adenosyl-L-methionine. Iwig, D.F., Booker, S.J. Biochemistry (2004) [Pubmed]
  13. Reinvestigation of the phenacyl bromide modification of alpha-chymotrypsin. Glover, G.I., Mariano, P.S., Petersen, J.R. Biochemistry (1976) [Pubmed]
  14. Total synthesis of cristatic acid. Fürstner, A., Gastner, T. Org. Lett. (2000) [Pubmed]
  15. Chemical synthesis and physiological activity of sulfonium analogues of platelet activating factor. Kates, M., Adams, G.A., Blank, M.L., Snyder, F. Lipids (1991) [Pubmed]
  16. Replacement of mouse LM fibroblast choline by a sulfonium analog. Effects on membrane properties as determined by virus probes. Anderson, R., Bilan, P. Biochim. Biophys. Acta (1981) [Pubmed]
  17. Autocatalytic formation of green heme: evidence for H2O2-dependent formation of a covalent methionine-heme linkage in ascorbate peroxidase. Metcalfe, C.L., Ott, M., Patel, N., Singh, K., Mistry, S.C., Goff, H.M., Raven, E.L. J. Am. Chem. Soc. (2004) [Pubmed]
  18. Selection of a high-energy bioactive conformation of a sulfonium-ion glycosidase inhibitor by the enzyme glucoamylase G2. Johnson, M.A., Jensen, M.T., Svensson, B., Pinto, B.M. J. Am. Chem. Soc. (2003) [Pubmed]
  19. S-adenosylmethionine conformations in solution and in protein complexes: conformational influences of the sulfonium group. Markham, G.D., Norrby, P.O., Bock, C.W. Biochemistry (2002) [Pubmed]
  20. Inhibitors of tRNA methyltransferases. S-Adenosylsulfonium salts. Gnegy, M.E., Lotspeich, F.J. J. Med. Chem. (1976) [Pubmed]
  21. Structure of the green heme in myeloperoxidase. Fenna, R., Zeng, J., Davey, C. Arch. Biochem. Biophys. (1995) [Pubmed]
  22. Synthetic decarboxylated S-adenosyl-L-methionine as a substrate for aminopropyl transferases. Dejima, H., Kobayashi, M., Takasaki, H., Takeda, N., Shirahata, A., Samejima, K. Biol. Pharm. Bull. (2003) [Pubmed]
  23. Methylation of glucagon, characterization of the sulfonium derivative, and regeneration of the native covalent structure. Rothgeb, T.M., Jones, B.N., Hayes, D.F., Gurd, R.S. Biochemistry (1977) [Pubmed]
  24. Specific and irreversible cyclopeptide inhibitors of dipeptidyl peptidase IV activity of the T-cell activation antigen CD26. Nguyen, C., Blanco, J., Mazaleyrat, J.P., Krust, B., Callebaut, C., Jacotot, E., Hovanessian, A.G., Wakselman, M. J. Med. Chem. (1998) [Pubmed]
  25. The specificity of interaction between S-adenosyl-L-methionine and a nucleolar 2'-O-methyltransferase. Segal, D.M., Eichler, D.C. Arch. Biochem. Biophys. (1989) [Pubmed]
  26. The Met243 sulfonium ion linkage is responsible for the anomalous magnetic circular dichroism and optical spectral properties of myeloperoxidase. Kooter, I.M., Koehler, B.P., Moguilevsky, N., Bollen, A., Wever, R., Johnson, M.K. J. Biol. Inorg. Chem. (1999) [Pubmed]
  27. Biliary excretion of a glutathione conjugate of busulfan and 1,4-diiodobutane in the rat. Marchand, D.H., Remmel, R.P., Abdel-Monem, M.M. Drug Metab. Dispos. (1988) [Pubmed]
  28. Evaluation of chemical and diastereoisomeric stability of S-adenosylmethionine in aqueous solution by capillary electrophoresis. Desiderio, C., Cavallaro, R.A., De Rossi, A., D'Anselmi, F., Fuso, A., Scarpa, S. Journal of pharmaceutical and biomedical analysis. (2005) [Pubmed]
  29. Efficient clustering of cyclic sulfonium salts applying liquid secondary ion mass spectrometry. Cozzolino, R., Gallagher, R.T., Drewello, T. European journal of mass spectrometry (Chichester, England) (2006) [Pubmed]
  30. Preparation and analysis of new sulfonium derivatives from S-adenosyl(5')-3-methylthiopropylamine. Oliva, A., Cacciapuoti, G., Romeo, G., Porcelli, M. Boll. Soc. Ital. Biol. Sper. (1979) [Pubmed]
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