Binding zwitterionic

Ion pair receptors can bind zwitterions such as amino acids. 

In 1992, de Mendoza and coworkers reported the synthesis of the bifunction-alized chiral bicyclic guanidinium 34 for the purpose of enantioselectively binding zwitterionic aromatic amino acids (i.e., tryptophan and phenylalanine) [55]. By including binding elements for the carboxylate and ammonium of the amino acids which were noncomplementary, they hoped to avoid the potential... 

The binding constants between the anionic substrates and cationic micelles are large because of the combination of coulombic and hydrophobic effects so rate enhancements may be large even with dilute surfactant. There is binding with non-ionic and zwitterionic micelles despite the absence of coulombic attraction (Bunton et al., 1975). 

Zwitterionic micelles of the sulfobetaine C16H33N+Me2(CH2)3SO 3 have effects very similar to those of cationic micelles (Table 7). This result is understandable if the substrate binds close to the quaternary ammonium center and the anionic sulfate moiety extends into the aqueous region. 

An X-ray crystal structure of 28 bound in the thumb-region of the NS5B polymerase showed little interaction of the acetamide moiety with the protein. Alterations at this position were explored in order to improve the physical properties of the compound. Incorporation of basic amines as part of this side-chain, leading to zwitterionic compounds, reduces plasma binding and has a beneficial effect on cell activity and pharmacokinetic profiles. In the cell-based replicon assay, racemic 29 has an EC50 of 152 nM in the presence of 10% fetal calf serum and 376 nM in the presence of 50% normal human serum [71],... 

The binding of pyridoxal 5 -phosphate (vitamin Be) to enzymes has been modelled using homo- and co-polypeptides containing L-lysine as a source of reactive amino groups. This has now been extended to reaction of pyridoxal with polyallylamine, with the polymer acting as a control that cannot provide amido -CO- or -NH- functions to stabilize the Schiff base products, as occurs in enzymes and polypeptides. Rate constants for the formation and hydrolysis of the imines have been measured and interpreted in terms of formation of the carbinolamine (in its neutral or zwitterionic form). 

Enolization and ketonization kinetics and equilibrium constants have been reported for phenylacetylpyridines (85a), and their enol tautomers (85b), together with estimates of the stability of a third type of tautomer, the zwitterion (85c). The latter provides a nitrogen protonation route for the keto-enol tautomerization. The two alternative acid-catalysed routes for enolization, i.e. O- versus Af-protonation, are assessed in terms of pK differences, and of equilibrium proton-activating factors which measure the C-H acidifying effects of the binding of a proton catalyst at oxygen or at nitrogen. 

The species shown in Schemes 8.1 and 8.2 do not contain vacant coordination sites suitable for binding weakly donating ligands such as alkenes. Even in Breslow s zwitterionic intermediate (Scheme 8.1) the nature of the metal-ethene interaction is unclear alkenes do not bind to the LUMO of 16-electron complexes CP2MCI2 (M = Ti, Zr, Hf) or their alkyl derivatives. The isolation by Eisch in 1985 of a cationic titanium vinyl complex [Cp2TiC(Ph)=C(Me)SiMe3], apparently formed by insertion of an alkyne into a putative [Cp2TiMe] intermediate [29], raised the... 

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