Hydrogen bonding and molecular recognition

Chang SK et al (1991) Hydrogen-bonding and molecular recognition - synthetic, complex-ation, and structural studies on barbiturate binding to an artificial receptor. J Am Chem Soc 113 7640-7645... 

A clear, brief, quantitative discussion of the contribution of hydrogen bonding to molecular recognition and enzyme catalysis. 

Adrian, J. C., Wilcox, C. S., Chemistry of synthetic receptors and functional-group arrays. 15. Effects of added water on thermodynamic aspects of hydrogen-bond-based molecular recognition in chloroform. J. Am. Chem. Soc. 1991, 113, 678-680. 

Figure 2.2 Typical examples of hydrogen bonding-based molecular recognition (a) thymine recognition (b) adenine recognition (c) flavin adenine dinucleotide recognition.21 (Reprinted with permission from K. Ariga and T. Kunitake, Acc. Chem. Res. 1998,31, 371-378. Copyright 1998 American Chemical Society.)...

Wilcox, C.S., Kim, E.I., Romano, D. et al. (1995) Experimental and theoretical studies of substituent effects in hydrogen bond based molecular recognition of a zwitterion by substituted arylureas. Tetrahedron, 51, 621-634. 

In the first case, simplified molecular versions of DNA or RNA can be used. Even though the supramolecular organization of nudeic acids is due to a subde balance of driving forces (i.e., electrostatic repulsion, n-staddng, and hydrogen bonding), the molecular recognition of complementary nucieobases (i.e., purine and pyrimidine heterocydes) can be... 

Discrimination of double-bond geometry by the reaction has also been one of the xmsolved problems in organic synthesis. Geometry-selective acylation and de-acylation of tri- and tetra-substituted olefins have been well developed by enzymatic methods [27 28 and references cited therein]. On the other hand, the non-enzymatic counterpart has scarcely been reported before our report in 2012 [29]. We found that double-bond geometry of tri- and tetrasubstituted alkenediols was effectively differentiated on their acylation via hydrogen-bond-mediated molecular recognition of the substrate structure by the catalyst. DMAP-catalyzed acylation of trisubstituted alkenediol 28 with NHNs substituent gave almost a 1 1 mixture of Z-0Ac and E-0Ac in 55% combined yield, which indicates the similar... 

Examples of hydrogen bond driven molecular recognition in low dielectric media. A. Kelly, T. R., and Maguire, M. P. 

Solid-state NMR and X-ray analysis of structural transformations in O-H - N heterosynthons formed by hydrogen-bond-mediated molecular recognition has been reported by Khan et Ambiguous peak splittings and the presence of unexpected resonances in the CP MAS NMR spectra have been successfully explained by the joint approach of X-ray analysis and DFT chemical shift computations. 

Molecular recognition of nucleobases and nucleotides at air-water interfaces (complementary hydrogen bonding and multisite interaction) 98ACR371. 

Etter, M. C., Z. Urbanczyk-Lipowska, M. Zia-Ebrahimi, and T. W. Pananto. 1990. Hydrogen Bond Directed Cocrystallization and Molecular Recognition Properties of Diaryl Ureas. J. Am Chem. Soc. 112, 8415. 

The interaction of drug molecules with biological membranes is a three-dimensional (3D) recognition that is mediated by surface properties such as shape, Van der Waals forces, electrostatics, hydrogen bonding, and hydrophobicity. Therefore, the GRID force field [5-7], which is able to calculate energetically favorable interaction sites around a molecule, was selected to produce 3D molecular interaction fields. 

Polytopic macrocyclic receptors 1, 2 (Figure 10.1) are able to complex the zwitterionic form of the amino acids by a double non-covalent charge interaction [28,29]. The unsymmetrical benzocrown sulfonamide derivative, 2 which contains benzo-18-crown-6 and benzo-15-crown-5 moieties was used as a ditopic receptor for multiple molecular recognition of the amino acids, by combining two non-covalent interactions ammonium-crown hydrogen bonding and carboxylate- complexed Na+-benzo-15-crown-5 charge interactions [28,33]. 

Intramolecular interaction is a powerful factor that controls molecular architecture, particularly in the case of geometrically flexible molecular systems. The existence and energies of intramolecular classical hydrogen bonds and their role in chemistry and biochemistry are well known. They stabilize molecular conformations, promote short- and long-range proton transfers, participate in the creation of three-dimensional structures of large molecules and play a fundamental role in the phenomenon of molecular recognition. 

Nucleic acids, proteins, some carbohydrates, and hormones are informational molecules. They carry directions for the control of biological processes. With the exception of hormones, these are macromolecules. In all these interactions, secondary forces such as hydrogen bonding and van der Waals forces, ionic bonds, and hydrophobic or hydrophilic characteristics play critical roles. Molecular recognition is the term used to describe the ability of molecules to recognize and interact bond—specifically with other molecules. This molecular recognition is based on a combination of the interactions just cited and on structure. 

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