Hydrogen-bonding receptors

Levitt M, Perutz MF. Aromatic rings act as hydrogen bond receptors, J Mol Biol 1988 201 751-754. 

Hydrogen bonds involve a hydrogen donor and a hydrogen bond receptor—e.g.—ethanol and acetone. 

Fan E, Vanarman SA, Kincaid S, Hamilton AD. Molecular recognition—hydrogen-bonding receptors that function in highly competitive solvents. J Am Chem Soc 1993 115 369-370. 

Lehn and coworkers have profitably employed tartaric acid-containing crown ethers as enzyme models. The rate of proton transfer to an ammonium-substituted pyridinium substrate from a tetra-l,4-dihydropyridine-substituted crown ether was considerably enhanced compared to that for a simple 1,4-dihydropyridine. The reaction showed first order kinetic data and was inhibited by potassium ions. Intramolecular proton transfer from receptor to substrate was thus inferred via the hydrogen bonded receptor-substrate complex shown in Figure 16a (78CC143). 

The crystal structure 57 of the strong and selective complex formed by the terephthalate dianion with a hexaprotonated macrobicyclic polyamine shows that it is a molecular cryptate 56 with the dianion tightly enclosed in the cavity and held by formation of three hydrogen bonds between each carboxylate and the ammonium groups [4.19]. Both structures 53 and 57 illustrate nicely what supermolecules really are they show two covalently built molecules bound to each other by a set of non-covalent interactions to form a well-defined novel entity of supramolecular nature. Acyclic [4.20a,b] and macrobicyclic [4.20c] hydrogen bonding receptors... 

Multiple recognition and catalysis in ATP hydrolysis with increased ATP/ADP selectivity has been achieved with a multifunctional anion receptor containing a macrocyclic polyamine as anion binding site, an acridine group as stacking site and a catalytic site for hydrolysis (structure 82) [4.27]. Phosphoryl transfer is accelerated by other types of hydrogen-bonding receptors [5.24a]. 

In 2004, Week and co-workers demonstrated that both mono- and multifunctional self-assembly could be employed simultaneously independently and reversibly on the same side-chain functionalized polymer [96]. A random terpolymer of poly(norbornene) was synthesized consisting of diaminopyridine (DAP) hydrogen-bonding receptors and a palladium-functionalized SCS-type pincer ligand for metal coordination-based self-assembly (Fig. 7.18). 

Finally, Week s group has also investigated the incorporation of two distinct hydrogen-bonding receptors (Fig. 7.21) along a single polymer backbone (both random and block copolymers were investigated) [93, 95]. 

V. Jubian, R.P. Dixon, A.D. Hamilton, Molecular Recognition and Catalysis - Acceleration of Phosphodiester Cleavage by a Simple Hydrogen-Bonding Receptor , J. Am. Chem. Soc., 114, 1120 (1992)... 

Another way of avoiding the problems of pH range and counterion competition is to use a neutral hydrogen-bonding receptor based on amide functionalities. Peptide groups from the protein backbone are, of course, well known to be involved in enzyme anion binding as discussed earlier. Amide involve-... 

R380 M. Inouye, Synthetic Hydrogen-Bonding Receptors for Biologically Essential Monosaccharides , Yuki Gosei Kagaku Kyokaishi, 2000, 58, 1077... 

Hydrogen-bond receptors (sum of nitrogen and oxygen atoms) less than 10... 

Synthetic hydrogen-bonding receptors (heterocycles) for biologically essential monosaccharides 00YGK1077. 

Jubian. V. Dixou. R.P. Hamilton, A.D. Molecular recognition and catalysis. Acceleration of phosphodiester cleavage by a simple hydrogen-bonding receptor. J. Am. Chem. Soc. 1992, 114 (3). 1120-1121. 

Linton, B.R. Goodman, M.S. Hamilton, A.D. Nitronate anion recognition and modualtion of ambient reactivity by hydrogen-bonding receptors. Chern. Eur. J. 2800, 5 (13), 2449-2455. 

Highly effective hydrogen-bonding receptors for guanine 75. derivatives. Angew. Chem., Int. Ed. Engl. 1995. 34 (19). 2163-2165. 

Bell. T.W. Hext, N.M. Khasanov, A.B. Binding biomolecules with designed, hydrogen-bonding receptors. Pure... 

Multivalent hydrogen bond receptors, (575) have been built from a tri-phenylene (574) core surrounded by six (diaryl)phosphinate groups (Scheme 140). In chloroform, (575) displayed recognition properties toward dihy-droxybenzenes, selectively forming complexes with catechol derivatives in a 1 2 (host guest) stoichiometry. ... 

Linton BR, Goodman MS, Hamilton AD. Nitronate anion recognition and modulation of ambident reactivity by hydrogen-bonding receptors. Chem Eur J. 2000,6 2449-2455. 

Scheme 23 Hydrogen-bonding receptors that act as A(LS)2 organogelators...

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