Thioether-containing derivative

This reaction raises a few important central issues in this chemistry. We saw previously that a similar thioether-containing derivative (see Eq. 

Varmenot N, Berges J, Abedinzadeh Z, Scemama A, Strzelczak G, Bobrowski K. (2004) Spectral, kinetics, and theoretical studies of sulfur-centered reactive intermediates derived from thioethers containing an acetyl group. J Phys Chem A 108 6331-6346. 

Imidazol-containing SBs have received much attention in the last decades as possible models for metalloenzymes. Thus, a series of asymmetrical tetradentate N2OS SBs (38,39) containing both imidazole and thioether functions derived from the precursors 4-[(2 -aminoethyl)thiomethyl (5-methylimidazole, 2-[(2 -aminoethyl)thiomethyll-benzimidazole and either sal (or derivatives), acetophenones, or acac have been prepared.103-106 These ligands behave as mono- or dianionic... 

Table 22 lists four polymer series of PEIs which contain an ether, sulphone or carbonyl linked diphenyl tetracarboxylimide unit [36]. Each of the four series contains two imide and two ester groups and have four aromatic co-monomers. Polymer series 7 and 9 also contain two units of p-aminophenol in conjunction with a bicyclic aromatic dicarboxylic acid, whereas polymer series 6 and 8 are based on m-aminophenol. The Mesogenic Index correctly predicts that series 6, 8 and 9 give rise to isotropic copolymers. However, in the case of series 7, in which the variable monomer was based on ether or thioether diphenol derivatives, thermotropic phases were observed in all three cases. When all four series are viewed as a whole it is clear that an MI value of 9.5 represents a borderline condition for a mesophase to occur. It also corresponds with the minimum value for a mesophase observed in NCPT-based PEIs. 

Poly(arylene thioether)s, 363-364 Poly(arylene thioether sulfone)s, 364 Poly(aryl sulfone) derivatives, 354 Poly(p-benzamide), synthesis of, 188-189 Polybenzimidazoles (PBIs), 265 ferrocene-containing, 315 synthesis of, 313... 

The first three-dimensional macrobicyclic TTF derivatives have been obtained <96CC615> and work on TTF-containing crown ethers and thioethers has continued <96LA551, 96JCS(P1)1995> with structures of this type being used to obtain the first TTF-containing... 

Sulfur-containing compounds [1-3] e.g. thiols [4, 5] and thioethers [5] sulfide ions [4] thiourea derivatives... 

In contrast to the large number of chiral pyridine derivatives used as ligands of metal complexes in asymmetric catalysis, only a few examples of chiral sulfur-containing pyridine ligands have so far been reported, such as pyridine thioethers derived from ( + )-camphor depicted in Scheme 1.33, which were assessed in the test reaction providing enantioselectivities of up to 76% ee. The related 2,2 -bipyridine thioethers were also prepared but showed a lower stereodilferentiating capability in the test reaction. 

Figure 5.9 SIAX can be used to modify amine-containing molecules to produce sulfhydryl-reactive derivatives. Subsequent reaction with a thiol compound produces a thioether linkage.

Figure 5.10 SIAC reacts with an amine-containing compound to yield an amide bond derivative that is reactive toward thiol-containing molecules. Secondary reaction with a sulfhydryl group gives a stable thioether bond.

BODIPY FL IA is insoluble in aqueous solution, but may be dissolved in DMF or DMSO as a concentrated stock solution prior to addition of a small aliquot to a reaction mixture. Coupling to sulfhydryl-containing molecules occurs rapidly with the formation of a thioether linkage. The reaction may be done in 50mM sodium borate, 5mM EDTA, pH 8.3. The main consideration is to protect the iodoacetyl derivative from light which may generate iodine and... 

Figure 9.34 The long side chain of this BODIPY derivative contains a sulfhydryl-reactive iodoacetamide group that can couple to a thiol group to form a thioether bond.

One Lucifer Yellow derivative is available for labeling sulfhydryl-containing molecules. Lucifer Yellow iodoacetamide is a 4-ethyliodoacetamide derivative of the basic disulfonate aminonaph-thalimide fluorophore structure (Invitrogen). The iodoacetyl groups react with —SH groups in proteins and other molecules to form stable thioether linkages (Figure 9.42). 

Figure 19.16 A common way of conjugating sulfhydryl-containing haptens to carrier proteins is to activate the carrier with sulfo-SMCC to create an intermediate maleimide derivative. The maleimide groups then can be coupled to thiols to form thioether bonds.

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