Aromatic stacking interaction

Adams H, Hunter CA, Lawson KR, Perkins J, Spey SE, Urch CJ, Sanderson JM. A supra-molecular system for quantifying aromatic stacking interactions. Eur J Chem 2001 7 4863-4877. 

Results from these experiments indicate that the aromatic stacking interaction between complementary strands is probably not the factor responsible for the stabilization of the cross-linked product in aqueous media. Instead, the critical role played by interstrand H bonding in the stabilization of products 19-20 (and similarly 21-22) was clearly demonstrated by the high sequence specificity of the cross-linking reactions, as well as by the behavior of control strands 24 and 25 in the presence of 20. 

Face-to-face aromatic stacking interactions are common in a wide range of organic charge-transfer compounds where there is a donor-acceptor interaction between an electron rich Ji-system and an electron... 

ML2 complexes with and these complexes show both aromatic stacking interactions and helical distortions. An nnusual S,N-chelate, with no carbon atoms in the four-membered chelate ring set, is (21) it forms a spirocyclic tetrahedral bis Co complex. 

Hydrogen bonding and aromatic aromatic—aromatic stacking interactions have also been used in the intermolecular organization of complementary... 

Newcomb and Gellman have examined aromatic stacking interactions in aqueous solution by studying intramolecular stacking interactions in the compounds shown in Figure 104 [135]. Their studies showed that neither hydrophobic nor dispersion interactions are responsible for the stacking observed under the conditions studied. 

Figure 104 Substrates used for studying aromatic stacking interactions in water [135]...

Aromatic-aromatic stacking interactions are significant contributors to protein structure stabilization (Burley and Petsko 1985). Modeling studies indicate that in the active state (R ) model of CBi, there is a patch of aromatic amino acids in the TMH 3-4-5 region with which WIN 55,212-2 can interact (McAllister et al. 2003). There is an upper (extracellular side) stack formed by F3.25(189 in human CBi, 190 in mouse CBi), W4.64(255/256), 5.39(275/276), and W5.43(279/280). When WIN 55,212-2 is computationally docked to interact with this patch, it also can interact with a lower (towards intracellular side) aromatic residue, F3.36(200/201). In this docking position, WIN 55,212-2 creates a continuous aromatic stack over... 

Anandamide was used as a control in this study, as aromatic stacking interactions are not key to its binding. However, according to the molecular model, F3.25A is a direct interaction site for anandamide. F3.25A had no effect on WIN 55,212-2 or SR141716A binding, but resulted in a sixfold loss in affinity for anandamide (McAllister et al. 2003). 

Huffman JW, Mabon R, Wu M-J, Lu J, Hart R, Hurst DP, Reggio PH, WUey JL, Martin BR (2003a) 3-Indolyl-l-naphthylmethanes new cannabimimetic indoles provide evidence for aromatic stacking interactions with the CB 1 cannabinoid receptor. Bioorg Med Chem 11 539-549... 

A recent modeling study of CBi reported by Salo and co-workers identified aromatic stacking interactions for SR141716A in the same aromatic cluster region of CBi, with direct aromatic stacking interactions identified between SR141716A and Y5.39 and W5.43 (Salo et al. 2004). 

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