ライフサイエンスコーパス: sulfonium

1 n through the formation of an unusual Fe(II) sulfonium.

2 Tris(trimethylsilyl)sulfonium 1 and methylbis(trimethylsilyl)sulfonium 2 ion

3 k(alpha)/k(normal)) 1.124 for dimethylphenyl sulfonium, 1.512 for dimethyl-1-naphthyl sulfonium, 1.83

4 nyl sulfonium, 1.512 for dimethyl-1-naphthyl sulfonium, 1.835 for dimethyl-9-anthracenyl sulfonium, a

5 lyl)sulfonium 1 and methylbis(trimethylsilyl)sulfonium 2 ions were prepared as long-lived species by

6 Our findings identify NSS-9 as a novel sulfonium alpha7 silent agonist that effectively allevia

7 d to a methionine-deficient diet, choline or sulfonium analogs of betaine induced BHMT expression.

8 erivative to chloride in comparison with the sulfonium analogue.

9 gold-catalyzed sigmatropic rearrangement of sulfonium and selenium ylides (39 examples, up to 99% yi

10 Sulfonium and selenonium salts, represented by S-aryl di

11 ped to prepare a series of tris(dialkylamino)sulfonium and sulfoxonium cations from sulfur monochlori

12 AdoMet facilitates reductive cleavage of the sulfonium and the generation of transient 5'-deoxyadenos

13 From the group of sulfoniums and sulfoxoniums explored in this work, the t

14 sulfonium, 1.835 for dimethyl-9-anthracenyl sulfonium, and 1.137 for S-methyldibenzylthiophenium.

15 m, proton removal at carbons adjacent to the sulfonium, and reductive cleavage to generate 5'-deoxyad

16 g the upper critical solution temperature of sulfonium- and ammonium-based polymer zwitterions in wat

17 The initially produced 1,3-betaine (o-sulfonium/aryl carbanion) undergoes intramolecular proto

18 ophysiological evaluation of a new series of sulfonium-based derivatives inspired by the archetypal s

19 plying selected ammonium-, phosphonium-, and sulfonium-based ionic liquids (IL) with bis(trifluoromet

20 re we have demonstrated that the presence of sulfonium-beta-sp(2) carbon and flexible, medium-sized s

21 We also determined the structures of one sulfonium bisphosphonate bound to farnesyl diphosphate s

22 results are of interest since they show that sulfonium bisphosphonates can have potent activity again

23 We investigated three series of sulfonium bisphosphonates for their activity in inhibiti

24 The third series consisted of 17 n-alkyl sulfonium bisphosphonates, the most active species havin

25 The first series consisted of 6 cyclic sulfonium bisphosphonates, the most active species havin

26 onsistent with the initial formation of a C2-sulfonium[bond]C1-oxosulfonium pyranosyl species upon ac

27 ection from dimethyl(2-hydroxy-5-nitrobenzyl)sulfonium bromide (DHNBS) oxidation.

28 reaction of dimethyl(2-hydroxy-5-nitrobenzyl)sulfonium bromide (HNSB) with tryptophan (Trp) residues

29 se charged interactions formed by the AdoMet sulfonium cation are stronger than typical CH...O hydrog

30 The sulfonium cations ((+)S(NR(2))(3)) typically degrade by

31 Molecular mechanics parameters for the sulfonium center have been developed for the AMBER force

32 that all three carbon atoms attached to the sulfonium center in SAM can serve as precursors to carbo

33 s initiated by the reductive cleavage of the sulfonium center of S-adenosyl-L-methionine (AdoMet), ge

34 not with positioning and orientation of the sulfonium center relative to the [4Fe-4S] cluster.

35 s spontaneously degraded by inversion of its sulfonium center to form the R,S diastereomer.

36 ymes that transfer the methyl group from the sulfonium center, but is more folded in complexes with p

37 on of 3-dimethylsulfoniopropionate (DMSP), a sulfonium compound produced by many marine algae.

38 Additionally, sulfonium compounds were tested on alpha9 nAChR, also in

39 beta-sp(2) carbon and flexible, medium-sized sulfonium-delta-substituents are crucial for SAM analogs

40 ivity profile, unprecedented for other vinyl sulfonium derivatives.

41 carbene based labeling system that utilizes sulfonium diazo probes.

42 y reaction of silane with tris(dimethylamino)sulfonium difluorotrimethylsilicate (TASF) or crypt[2.1.

43 reagents and 1.5 equiv of tris(dimethylamino)sulfonium difluorotrimethylsilicate (TASF).

44 termediate 65 with TAS-F (tris(dimethylamino)sulfonium difluorotrimethylsilicate), thereby completing

45 arbamidomethylation of Met residues leads to sulfonium ether formation, and the resulting fixed posit

46 the high reaction efficiency and the lack of sulfonium formation.

47 mechanism involving the formation of the C2-sulfonium glycosyl imidate 39 as well as oxazoline 37 as

48 s provide insights into the potential of the sulfonium group as a chemotype interacting with the alph

49 tic interactions with the positively charged sulfonium group of SAM, thereby providing a basis for di

50 Met for uptake required a positively charged sulfonium group on the 5' position of the ribose.

51 first of which is racemization of the chiral sulfonium group, which takes place in a pH-independent m

52 both selectively generate the requisite bis-sulfonium intermediate and drive its rapid elimination i

53 The fate of the initial sulfonium intermediate was investigated by mechanistic e

54 he starting alkene into a transient 1,3-iodo-sulfonium intermediate, which undergoes sequential nucle

55 sformation of alkenes into transient 1,2-bis-sulfonium intermediates found to undergo Z-selective eli

56 proach relying on electron redistribution in sulfonium intermediates.

57 ol (TG, 71%) and a minor amount of the CH-TG sulfonium ion (12%), although some elimination of HCl is

58 angement to form a reactive methyl(methylene)sulfonium ion (CH(2)=S(+)-Me).

59 for this enzyme yielding methyl ethyl vinyl sulfonium ion (MEVS+) upon reaction with S-adenosylmethi

60 The more reactive isomeric sulfonium ion 22 was discounted as being responsible for

61 lations suggesting a barrierless pathway for sulfonium ion 27 to react with the cycloalkene.

62 erences in reactivity, thiiranium ion 25 and sulfonium ion 27 were formed independently, with the lat

63 a hydrogen-bonded complex is formed between sulfonium ion and acceptor that undergoes SN2-like glyco

64 Displacement of the sulfonium ion by a hydroxyl leads to the stereoselective

65 boronate was converted to the corresponding sulfonium ion by treatment with methyl iodide and subseq

66 Recent findings reveal that a sulfonium ion can replace the quaternary ammonium nitrog

67 Under physiological conditions, however, the sulfonium ion can spontaneously racemize to the R form,

68 our different inhibitors: acarbose and three sulfonium ion compounds.

69 ophosphoserine lipids using a "fixed charge" sulfonium ion containing, d(6)-S,S'-dimethylthiobutanoyl

70 to afford an electrophilic methyl(methylene)sulfonium ion for reaction with a carbon nucleophile fol

71 city of the amido anion contained within the sulfonium ion intermediate and facilitates the rate of t

72 observations support a mechanism by which a sulfonium ion intermediate is formed as a trans-decalin

73 convincingly the presence of the beta-linked sulfonium ion intermediate.

74 Due to steric and electronic factors, the sulfonium ion is formed as a trans-decalin ring system.

75 vidence for the formation of an intermediate sulfonium ion is provided, as are data from nucleophilic

76 rrole rings A and C of the heme as well as a sulfonium ion linkage between the sulfur atom of Met(243

77 results in the formation of a bicyclic beta-sulfonium ion that after addition of an alcohol undergoe

78 mpted preparation of dimethyl(trimethylsilyl)sulfonium ion under similar conditions failed as a resul

79 t of covalent reaction of methyl ethyl vinyl sulfonium ion with the enzyme as shown by comigration of

80 ich yields the nonreactive product trimethyl sulfonium ion, protected the enzyme from inactivation by

81 initial evaluation of a novel "fixed charge" sulfonium ion-containing crosslinking reagent, S-methyl

82 ents ring-opening, enabling isolation of the sulfonium ion-pair intermediate.

83 Specifically, cyclized sulfonium ion-pair intermediates are diverted to alkenes

84 diastereoisomeric states with respect to its sulfonium ion.

85 articipation to give a quasi-stable anomeric sulfonium ion.

86 attacks the methylene carbon adjacent to the sulfonium ion.

87 Methyl(methylene)sulfonium ions (CH(2)=S(+)-Me) were generated by simple

88 Anomeric sulfonium ions are attractive glycosyl donors for the st

89 Vinyl sulfonium ions are demonstrated to react with carbon-cen

90 Since vinyl sulfonium ions are reactive toward nucleophiles, the ina

91 The sulfonium ions are sufficiently stable at a temperature

92 d easily be converted into bicyclic anomeric sulfonium ions by oxidization to sulfoxides and arylated

93 The resulting sulfonium ions gave high 1,2-cis-anomeric selectivity wh

94 S-Adenosylmethionine (AdoMet) and other sulfonium ions play central roles in the metabolism of a

95 The reactivities of acylated and unacylated sulfonium ions that were analogues of S-adenosylmethioni

96 e method to convert thioglycosides into beta-sulfonium ions via an intramolecular alkylation reaction

97 AdoMet and two other biologically important sulfonium ions, S-methylmethionine and dimethylsulfoniop

98 ethers by methylation to form reactive vinyl sulfonium ions.

99 -ium triflate, a weak partial agonist with a sulfonium isostere of the ammonium pharmacophore.

100 symmetric [3,3]-sigmatropic rearrangement of sulfonium leads after cyclization to cyclopentenones wit

101 The resultant Z-alkenyl sulfonium linchpins provide access to a wide array of Z-

102 se of myeloperoxidase, through an additional sulfonium link from the Cbeta of the 2-vinyl group to a

103 To duplicate the sulfonium link in myeloperoxidase and to obtain informat

104 o this reaction revealed a novel process for sulfonium-mediated oxidation of glycal enol ethers in wh

105 styryl]benzene core with covalently attached sulfonium moieties, has been synthesized.

106 gin (SFG) is a SAM analog in which the S-CH3 sulfonium moiety of SAM is replaced by a C-NH2 amine.

107 idue (tyrosine 68) behind the methyl-bearing sulfonium of AdoMet was previously shown to impair COMT

108 ive charge at the position equivalent to the sulfonium of S-adenosylmethionine.

109 , and there is no discrimination between the sulfonium of SAM or the thioether of SAH.

110 These studies indicated that the sulfonium-pai interaction is the strongest and that pola

111 monium group also contribute to the stronger sulfonium-pai interaction.

112 In comparing sulfonium-pai versus sulfur-pai interactions in proteins

113 We report the measurement and analysis of sulfonium-pai, thioether-pai, and ammonium-pai interacti

114 Further, sulfonium PEG polyelectrolytes can be obtained via alkyl

115 e (ACC) synthases and is positioned near the sulfonium pole of (S,S)-S-adenosyl-L-methionine (SAM) in

116 upport a role for Glu47 as an anchor for the sulfonium pole of (S,S)-SAM, and consequently a role as

117 oped an electrochemical method for preparing sulfonium polyelectrolytes by C-H functionalization of p

118 3)C-methyl]-SAM complex show that the target sulfonium positioning varies with the cation, while the

119 1-hydroxy glycosyl donors employing dialkyl sulfonium reagents is described.

120 presence of DBU, is dehydrated by activated sulfonium reagents to generate the corresponding isocyan

121 ve deployment of enantiopure sulfinimines in sulfonium rearrangements, and at once solves the problem

122 contributes to the stronger interaction with sulfonium relative to ammonium.

123 gement, intramolecular spirocyclization, and sulfonium ring-opening.

124 e and nonhygroscopic monosubstituted allenyl sulfonium salt (ATT) synthesized from thianthrene and pr

125 cation mechanism leading to the formation of sulfonium salt 18.

126 Using dibenzothiophene sulfonium salt chemistry, [(18)F]AldoView was obtained i

127 ces in controlling the reactivity of alkenyl sulfonium salt electrophiles.

128 The isolation and characterization of a sulfonium salt intermediate supports an interrupted Pumm

129 The sulfonium salt label renders inconsequential the electro

130 Intramolecular interactions from sulfonium salt tethered to phenylalkyne were highlighted

131 The reagent is the first allenyl sulfonium salt that can undergo palladium-catalyzed cros

132 PAH-sulfonium salts 1Me+, 1Et+, 10Me+, 10Et+, 12Me+, and 14M

133 oratories, was employed utilizing the chiral sulfonium salts 22 and 23.

134 Sulfonium salts 3 and 4 do not appear to interconvert, a

135 New EDA complexation strategies exploiting sulfonium salts allow radicals to be generated from nati

136 wcases the first described attempt where the sulfonium salts and arenesulfonyl chlorides were success

137 diversities of bench-stable and easy-to-use sulfonium salts and arenesulfonyl chlorides.

138 ane synthesis, through the reaction of vinyl sulfonium salts and sulfones under mild conditions.

139 These azulene sulfonium salts are bench-stable species that may be emp

140 The corresponding sulfonium salts are formed in a highly regio- and stereo

141 tudies demonstrate that these triphenylamine sulfonium salts are highly efficient cationic photoiniti

142 Finally, an analysis of sulfonium salts as electron acceptors will demonstrate h

143 ghly functionalized aromatic compounds using sulfonium salts as leaving groups.

144 Interestingly, only mono- or disubstituted sulfonium salts can be prepared.

145 These oligomeric sulfonium salts exist as free-flowing powders and are st

146 rived from readily available camphor-derived sulfonium salts for the synthesis of glycidic amides hav

147 alpha-alkylidene pyrazolinones and propargyl sulfonium salts has been developed to construct function

148 The alpha-effects for the series of sulfonium salts in completion reactions for 3-ClNMBH ani

149 The propargyl sulfonium salts obtained by alkylation of thioethers 7,

150 S-alkyl and S-aryl orbitals of the starting sulfonium salts provide additional insight.

151 The formation of these sulfonium salts represents additional products in the di

152 To address this, we prepared sulfonium salts that produced a pH drop within HCT 116 c

153 On the other hand, the efficiencies of the sulfonium salts toward the photopolymerization of cycloh

154 st-order rate constants of the solvolysis of sulfonium salts were determined in mixtures containing d

155 In this review, these new applications of sulfonium salts will be introduced and the areas of chem

156 Reaction of the resultant sulfonium salts with alkyllithium/magnesium reagents gen

157 The sulfonium salts with tertiary alkyl and vinyl substituen

158 es, diaryliodonium salts, or dimethyl(phenyl)sulfonium salts with trifluoroacetamides affords substit

159 For example, aryl sulfonium salts, formed by the activation of arenes, can

160 tally inhibits the catalytic activity of the sulfonium salts, the selenonium salt remains catalytical

161 butane-, oxetane-, and azetidine-substituted sulfonium salts, which can undergo Johnson-Corey-Chaykov

162 pture nucleophiles and electrophiles to give sulfonium salts, which subsequently enable the formation

163 alkoxy radicals-via the formation of alkoxy sulfonium salts-that react with alkenes en route to 1,2-

164 simple (pseudo)halides or other conventional sulfonium salts.

165 nd rearrangement of little-known alpha-amido sulfonium salts; the amide motif "catches" the sulfoxide

166 Sulfonium, selenonium, telluronium, and iodonium cyanobo

167 The chiral sulfonium spontaneously racemizes to form a mixture of S

168 exene oxide depend on the counterion and the sulfonium substituents.

169 tal hydroxyl to the S(IV)-center of putative sulfonium sulfonate 6.

170 ith an electrostatic interaction between the sulfonium sulfur and the carboxylate group is not notice

171 The sulfonium sulfur is in van der Waals contact with a prot

172 conformation in which the positively charged sulfonium sulfur is near an electronegative oxygen in th

173 s involving the sulfur and which can use the sulfonium sulfur solely as a binding site.

174 This "sulfonium tag" approach relaxes the electronic constrain

175 ared via the reaction of dimethyl(methylthio)sulfonium tetrafluoroborate (DMSTF) with beta-alkoxy-gam

176 tituted thioacetals with dimethyl(methylthio)sulfonium tetrafluoroborate (DMTSF) produces synthetical

177 ared via the reaction of dimethyl(methylthio)sulfonium tetrafluoroborate (DMTSF) with beta-alkoxy-gam

178 carbonyl compounds with dimethyl(methylthio)sulfonium tetrafluoroborate (DMTSF).

179 OBr, HOCl, CH(3)SCl, and dimethyl(methylthio)sulfonium tetrafluoroborate (DMTSF)/NaN(3) with a variet

180 t of cycloadduct 17 with dimethyl(methylthio)sulfonium tetrafluoroborate gave 2,5,6,7-tetrahydropyrro

181 A stable dimethyl(thiodimethyl)sulfonium tetrafluoroborate salt was employed for the el

182 on reactions using the dimethyl(thiodimethyl)sulfonium tetrafluoroborate salt with diphenylacetylene

183 philes provided facile access to pyridinium, sulfonium, thiol, carbonitrile, acetoxy, and amino deriv

184 hanesulfonic acid- and dimethyl (thiomethyl) sulfonium trifluoromethanesulfonate-promoted systems.

185 e two vinyl groups of heme b but lacks the 2-sulfonium-vinyl linkage of heme m.

186 Interactions of the sulfonium with aromatic rings are rarely observed.

187 tal lineCH-Acc, 2) with pyridinium ylides 3, sulfonium ylide 4, and sulfonyl-substituted chloromethyl

188 presented that suggests that the hydroperoxy sulfonium ylide exists in both diradical and zwitterioni

189 is formed via rearrangement of a hydroperoxy sulfonium ylide intermediate.

190 in terms of partitioning of the hydroperoxy sulfonium ylide intermediate.

191 eogenic allylic carbon center using a chiral sulfonium ylide is demonstrated.

192 have low BDEs, unless the sulfilimine or S,C-sulfonium ylide is stabilized by an electronegative subs

193 orged through the Stevens rearrangement of a sulfonium ylide, generated in situ from the coupling of

194 d acrylates with high ee and that stabilized sulfonium ylides (e.g., ester-stabilized) reacted with c

195 d previously been found that semi-stabilized sulfonium ylides (e.g., Ph-stabilized) reacted with cycl

196 Photolysis of S,C-sulfonium ylides derived from thioanisol, thiophene, ben

197 N-H sulfilimines and CH2-S,C-sulfonium ylides have low BDEs, unless the sulfilimine o

198 in situ-generated cyclopropanones with acyl sulfonium ylides representing a formal carbene insertion

199 rsulfoxides, thiadioxiranes, and hydroperoxy sulfonium ylides were located and their structures analy

200 y has focused on the reactions of stabilized sulfonium ylides with acyclic enones which unexpectedly

201 the following: sulfoxides, sulfilimines, S,C-sulfonium ylides, and selenoxides.

202 ions were carried out with deuterium-labeled sulfonium ylides, higher ee's were observed in all cases

203 ately access regio- and stereodefined cyclic sulfonium zwitterions via the slower but thermodynamical