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Volumn 6, Issue 6, 2002, Pages 736-741

Aromatic interactions in model systems

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUND; PEPTIDE; SOLVENT; AROMATIC AMINO ACID; AROMATIC HYDROCARBON; DNA;

EID: 0036897848     PISSN: 13675931     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1367-5931(02)00359-9     Document Type: Review
Times cited : (403)

References (37)
  • 1
    • 0034979126 scopus 로고    scopus 로고
    • Hydrogen bonding, base stacking, and steric effects in DNA replication
    • Kool E.T. Hydrogen bonding, base stacking, and steric effects in DNA replication. Annu Rev Biophys Biomol Struct. 30:2001;1-22.
    • (2001) Annu Rev Biophys Biomol Struct , vol.30 , pp. 1-22
    • Kool, E.T.1
  • 2
    • 0034495733 scopus 로고    scopus 로고
    • Aromatic clusters: A determinant of thermal stability of thermophilic proteins
    • Aromatic interactions are proposed to contribute to the thermal stability of thermophilic proteins in this article
    • Kannan N., Vishveshwara S. Aromatic clusters: a determinant of thermal stability of thermophilic proteins. Protein Eng. 13:2000;753-761. Aromatic interactions are proposed to contribute to the thermal stability of thermophilic proteins in this article.
    • (2000) Protein Eng , vol.13 , pp. 753-761
    • Kannan, N.1    Vishveshwara, S.2
  • 3
    • 0036135139 scopus 로고    scopus 로고
    • A possible role for pi-stacking in the self-assembly of amyloid fibrils
    • Gazit E. A possible role for pi-stacking in the self-assembly of amyloid fibrils. FASEB J. 16:2002;77-83.
    • (2002) FASEB J , vol.16 , pp. 77-83
    • Gazit, E.1
  • 4
    • 0036216060 scopus 로고    scopus 로고
    • Aromatic-aromatic interactions in and around alpha-helices
    • Bhattacharyya R., Samanta U., Chakrabarti P. Aromatic-aromatic interactions in and around alpha-helices. Protein Eng. 15:2002;91-100.
    • (2002) Protein Eng , vol.15 , pp. 91-100
    • Bhattacharyya, R.1    Samanta, U.2    Chakrabarti, P.3
  • 5
    • 0036721382 scopus 로고    scopus 로고
    • Aromatic side-chain interactions in proteins. I. Main structural features
    • These papers (see also [6]) describe where aromatic interactions are favored in protein structures
    • Thomas A., Meurisse R., Charloteaux B., Brasseur R. Aromatic side-chain interactions in proteins. I. Main structural features. Proteins. 48:2002;628-634. These papers (see also [6]) describe where aromatic interactions are favored in protein structures.
    • (2002) Proteins , vol.48 , pp. 628-634
    • Thomas, A.1    Meurisse, R.2    Charloteaux, B.3    Brasseur, R.4
  • 6
    • 0036721415 scopus 로고    scopus 로고
    • Aromatic side-chain interactions in proteins. II. Near- and far-sequence Phe-X pairs
    • Thomas A., Meurisse R., Brasseur R. Aromatic side-chain interactions in proteins. II. Near- and far-sequence Phe-X pairs. Proteins. 48:2002;635-644.
    • (2002) Proteins , vol.48 , pp. 635-644
    • Thomas, A.1    Meurisse, R.2    Brasseur, R.3
  • 7
    • 0032546782 scopus 로고    scopus 로고
    • Pi-stacking interactions - Alive and well in proteins
    • McGaughey G.B., Gagne M., Rappe A.K. Pi-stacking interactions - alive and well in proteins. J Biol Chem. 273:1998;15458-15463.
    • (1998) J Biol Chem , vol.273 , pp. 15458-15463
    • McGaughey, G.B.1    Gagne, M.2    Rappe, A.K.3
  • 8
    • 0022419375 scopus 로고
    • Aromatic-aromatic interaction - A mechanism of protein-structure stabilization
    • Burley S.K., Petsko G.A. Aromatic-aromatic interaction - a mechanism of protein-structure stabilization. Science. 229:1985;23-28.
    • (1985) Science , vol.229 , pp. 23-28
    • Burley, S.K.1    Petsko, G.A.2
  • 9
    • 0025756736 scopus 로고
    • Aromatic aromatic interactions and protein stability - Investigation by double-mutant cycles
    • Serrano L., Bycroft M., Fersht A.R. Aromatic aromatic interactions and protein stability - investigation by double-mutant cycles. J Mol Biol. 218:1991;465-475.
    • (1991) J Mol Biol , vol.218 , pp. 465-475
    • Serrano, L.1    Bycroft, M.2    Fersht, A.R.3
  • 10
    • 0037079679 scopus 로고    scopus 로고
    • Investigation of a conserved stacking interaction in target site recognition by the U1A protein
    • Shiels J.C., Tuite J.B., Nolan S.J., Baranger A.M. Investigation of a conserved stacking interaction in target site recognition by the U1A protein. Nucleic Acids Res. 30:2002;550-558.
    • (2002) Nucleic Acids Res , vol.30 , pp. 550-558
    • Shiels, J.C.1    Tuite, J.B.2    Nolan, S.J.3    Baranger, A.M.4
  • 11
    • 0033615310 scopus 로고    scopus 로고
    • Recognition of an essential adenine at a protein-RNA interface: Comparison of the contributions of hydrogen bonds and a stacking interaction
    • Nolan S.J., Shiels J.C., Tuite J.B., Cecere K.L., Baranger A.M. Recognition of an essential adenine at a protein-RNA interface: comparison of the contributions of hydrogen bonds and a stacking interaction. J Am Chem Soc. 121:1999;8951-8952.
    • (1999) J Am Chem Soc , vol.121 , pp. 8951-8952
    • Nolan, S.J.1    Shiels, J.C.2    Tuite, J.B.3    Cecere, K.L.4    Baranger, A.M.5
  • 12
    • 0035528860 scopus 로고    scopus 로고
    • Aromatic interactions
    • This is an excellent recent review of aromatic interactions
    • Hunter CA, Lawson KR, Perkins J, Urch CJ: Aromatic interactions. J Chem Soc Perkin Trans. 2001:651-669. This is an excellent recent review of aromatic interactions.
    • (2001) J Chem Soc Perkin Trans , pp. 651-669
    • Hunter, C.A.1    Lawson, K.R.2    Perkins, J.3    Urch, C.J.4
  • 13
    • 0001227655 scopus 로고
    • The nature of pi-pi Interactions
    • Hunter C.A., Sanders J.K.M. The nature of pi-pi Interactions. J Am Chem Soc. 112:1990;5525-5534.
    • (1990) J Am Chem Soc , vol.112 , pp. 5525-5534
    • Hunter, C.A.1    Sanders, J.K.M.2
  • 14
    • 0001017381 scopus 로고    scopus 로고
    • Theoretical studies of the supramolecular synthon benzene-hexafluorobenzene
    • West J., Mecozzi S., Dougherty D.A. Theoretical studies of the supramolecular synthon benzene-hexafluorobenzene. J Phys Org Chem. 10:1997;347-350.
    • (1997) J Phys Org Chem , vol.10 , pp. 347-350
    • West, J.1    Mecozzi, S.2    Dougherty, D.A.3
  • 15
    • 0343417831 scopus 로고
    • Interaction between stacked aryl groups in 1,8- diarylnaphthalenes - Dominance of polar/pi over charge-transfer effects
    • Cozzi F., Siegel J.S. Interaction between stacked aryl groups in 1,8- diarylnaphthalenes - dominance of polar/pi over charge-transfer effects. Pure Appl Chem. 67:1995;683-689.
    • (1995) Pure Appl Chem , vol.67 , pp. 683-689
    • Cozzi, F.1    Siegel, J.S.2
  • 16
    • 0034721423 scopus 로고    scopus 로고
    • Three-state, conformational probe for hydrophobic, pi-stacking interactions in aqueous and mixed aqueous solvent systems: Anisotropic solvation of aromatic rings
    • Sindkhedkar M.D., Mulla H.R., Cammers-Goodwin A. Three-state, conformational probe for hydrophobic, pi-stacking interactions in aqueous and mixed aqueous solvent systems: anisotropic solvation of aromatic rings. J Am Chem Soc. 122:2000;9271-9277.
    • (2000) J Am Chem Soc , vol.122 , pp. 9271-9277
    • Sindkhedkar, M.D.1    Mulla, H.R.2    Cammers-Goodwin, A.3
  • 17
    • 0034703708 scopus 로고    scopus 로고
    • Solvophobically driven pi-stacking of phenylene ethynylene macrocycles and oligomers
    • Lahiri S., Thompson J.L., Moore J.S. Solvophobically driven pi-stacking of phenylene ethynylene macrocycles and oligomers. J Am Chem Soc. 122:2000;11315-11319.
    • (2000) J Am Chem Soc , vol.122 , pp. 11315-11319
    • Lahiri, S.1    Thompson, J.L.2    Moore, J.S.3
  • 18
    • 0037117444 scopus 로고    scopus 로고
    • Helicogenicity of solvents in the conformational equilibrium of oligo(m-phenylene ethynylene)s: Implications for foldamer research
    • This is a thorough solvent study of aromatic interactions
    • Hill D.J., Moore J.S. Helicogenicity of solvents in the conformational equilibrium of oligo(m-phenylene ethynylene)s: implications for foldamer research. Proc Natl Acad Sci USA. 99:2002;5053-5057. This is a thorough solvent study of aromatic interactions.
    • (2002) Proc Natl Acad Sci USA , vol.99 , pp. 5053-5057
    • Hill, D.J.1    Moore, J.S.2
  • 19
    • 0029935228 scopus 로고    scopus 로고
    • Aromatic pi-stacking in solution as revealed through the aggregation of phenylacetylene macrocycles
    • Shetty A.S., Zhang J.S., Moore J.S. Aromatic pi-stacking in solution as revealed through the aggregation of phenylacetylene macrocycles. J Am Chem Soc. 118:1996;1019-1027.
    • (1996) J Am Chem Soc , vol.118 , pp. 1019-1027
    • Shetty, A.S.1    Zhang, J.S.2    Moore, J.S.3
  • 21
    • 0034720952 scopus 로고    scopus 로고
    • Solvent-dependent stabilization of the E configuration of propargylic secondary amides
    • Gardner R.R., McKay S.L., Gellman S.H. Solvent-dependent stabilization of the E configuration of propargylic secondary amides. Org Lett. 2:2000;2335-2338.
    • (2000) Org Lett , vol.2 , pp. 2335-2338
    • Gardner, R.R.1    McKay, S.L.2    Gellman, S.H.3
  • 22
    • 0034802469 scopus 로고    scopus 로고
    • H-1 NMR investigation of solvent effects in aromatic stacking interactions
    • This paper provides a clear example of the contribution of both solvophobic and electrostatic contributions to aromatic interactions
    • Cubberley M.S., Iverson B.L. H-1 NMR investigation of solvent effects in aromatic stacking interactions. J Am Chem Soc. 123:2001;7560-7563. This paper provides a clear example of the contribution of both solvophobic and electrostatic contributions to aromatic interactions.
    • (2001) J Am Chem Soc , vol.123 , pp. 7560-7563
    • Cubberley, M.S.1    Iverson, B.L.2
  • 23
    • 0001660487 scopus 로고    scopus 로고
    • Structure-activity relationship for quantifying aromatic interactions
    • Carver FJ, Hunter CA, Seward EM: Structure-activity relationship for quantifying aromatic interactions. Chem Commun. 1998:775-776.
    • (1998) Chem Commun , pp. 775-776
    • Carver, F.J.1    Hunter, C.A.2    Seward, E.M.3
  • 24
    • 12044259820 scopus 로고
    • Chemistry of synthetic receptors and functional-group arrays. 24. Molecular torsion balance for weak molecular recognition forces - Effects of tilted-t edge-to-face aromatic interactions on conformational selection and solid-state structure
    • Paliwal S., Geib S., Wilcox C.S. Chemistry of synthetic receptors and functional-group arrays. 24. Molecular torsion balance for weak molecular recognition forces - effects of tilted-t edge-to-face aromatic interactions on conformational selection and solid-state structure. J Am Chem Soc. 116:1994;4497-4498.
    • (1994) J Am Chem Soc , vol.116 , pp. 4497-4498
    • Paliwal, S.1    Geib, S.2    Wilcox, C.S.3
  • 25
    • 0032483756 scopus 로고    scopus 로고
    • Measurements of molecular electrostatic field effects in edge-to-face aromatic interactions and CH-pi interactions with implications for protein folding and molecular recognition
    • Kim E., Paliwal S., Wilcox C.S. Measurements of molecular electrostatic field effects in edge-to-face aromatic interactions and CH-pi interactions with implications for protein folding and molecular recognition. J Am Chem Soc. 120:1998;11192-11193.
    • (1998) J Am Chem Soc , vol.120 , pp. 11192-11193
    • Kim, E.1    Paliwal, S.2    Wilcox, C.S.3
  • 26
    • 85047696400 scopus 로고    scopus 로고
    • Influence of highly preorganised 7,7-diphenylnorbornane in the free energy of edge-to-face aromatic interactions
    • Martinez A.G., Barcina J.O., Cerezo A.D. Influence of highly preorganised 7,7-diphenylnorbornane in the free energy of edge-to-face aromatic interactions. Chem Eur J. 7:2001;1171-1175.
    • (2001) Chem Eur J , vol.7 , pp. 1171-1175
    • Martinez, A.G.1    Barcina, J.O.2    Cerezo, A.D.3
  • 30
    • 0035902252 scopus 로고    scopus 로고
    • Model systems for flavoenzyme activity. Control of flavin recognition via specific electrostatic interactions
    • Goodman A.J., Breinlinger E.C., McIntosh C.M., Grimaldi L.N., Rotello V.M. Model systems for flavoenzyme activity. Control of flavin recognition via specific electrostatic interactions. Org Lett. 3:2001;1531-1534.
    • (2001) Org Lett , vol.3 , pp. 1531-1534
    • Goodman, A.J.1    Breinlinger, E.C.2    McIntosh, C.M.3    Grimaldi, L.N.4    Rotello, V.M.5
  • 31
    • 0037028989 scopus 로고    scopus 로고
    • Unexpected substituent effects in offset pi-pi stacked interactions in water
    • Rashkin M.J., Waters M.L. Unexpected substituent effects in offset pi-pi stacked interactions in water. J Am Chem Soc. 124:2002;1860-1861.
    • (2002) J Am Chem Soc , vol.124 , pp. 1860-1861
    • Rashkin, M.J.1    Waters, M.L.2
  • 32
    • 0037151644 scopus 로고    scopus 로고
    • Contribution of aromatic Interactions to α-helix stability
    • Butterfield S.M., Patel P.R., Waters M.L. Contribution of aromatic Interactions to α-helix stability. J Am Chem Soc. 124:2002;9751-9755.
    • (2002) J Am Chem Soc , vol.124 , pp. 9751-9755
    • Butterfield, S.M.1    Patel, P.R.2    Waters, M.L.3
  • 33
    • 0037077578 scopus 로고    scopus 로고
    • Selective aromatic interactions in β-hairpin peptides
    • This paper clearly demonstrates the selectivity of aromatic interactions relative to aliphatic interactions in a peptide model system
    • Tatko C.D., Waters M.L. Selective aromatic interactions in β-hairpin peptides. J Am Chem Soc. 124:2002;9372-9373. This paper clearly demonstrates the selectivity of aromatic interactions relative to aliphatic interactions in a peptide model system.
    • (2002) J Am Chem Soc , vol.124 , pp. 9372-9373
    • Tatko, C.D.1    Waters, M.L.2
  • 34
    • 0034654495 scopus 로고    scopus 로고
    • Factors contributing to aromatic stacking in water: Evaluation in the context of DNA
    • This is a thorough paper investigating the correlation between a dangling aromatic group and duplex DNA stability
    • Guckian K.M., Schweitzer B.A., Ren R.X.F., Sheils C.J., Tahmassebi D.C., Kool E.T. Factors contributing to aromatic stacking in water: evaluation in the context of DNA. J Am Chem Soc. 122:2000;2213-2222. This is a thorough paper investigating the correlation between a dangling aromatic group and duplex DNA stability.
    • (2000) J Am Chem Soc , vol.122 , pp. 2213-2222
    • Guckian, K.M.1    Schweitzer, B.A.2    Ren, R.X.F.3    Sheils, C.J.4    Tahmassebi, D.C.5    Kool, E.T.6
  • 35
    • 0036009267 scopus 로고    scopus 로고
    • Modified purine nucleosides as dangling ends of DNA duplexes: The effect of the nucleobase polarizability on stacking interactions
    • Rosemeyer H, Seela F: Modified purine nucleosides as dangling ends of DNA duplexes: The effect of the nucleobase polarizability on stacking interactions. J Chem Soc Perkin Trans. 2002:746-750.
    • (2002) J Chem Soc Perkin Trans , pp. 746-750
    • Rosemeyer, H.1    Seela, F.2
  • 36
    • 0037165683 scopus 로고    scopus 로고
    • On the effect of covalently appended quinolones on termini of DNA duplexes
    • This paper provides a detailed structural investigation of a dangling aromatic group and demonstrates that not all dangling aromatics stack at the terminus of the duplex
    • Tuma J., Connors W.H., Stitelman D.H., Richert C. On the effect of covalently appended quinolones on termini of DNA duplexes. J Am Chem Soc. 124:2002;4236-4246. This paper provides a detailed structural investigation of a dangling aromatic group and demonstrates that not all dangling aromatics stack at the terminus of the duplex.
    • (2002) J Am Chem Soc , vol.124 , pp. 4236-4246
    • Tuma, J.1    Connors, W.H.2    Stitelman, D.H.3    Richert, C.4
  • 37
    • 0035857392 scopus 로고    scopus 로고
    • Beyond the hydrophobic effect: Attractions involving heteroaromatic rings in aqueous solution
    • This paper provides the only example of the stacking of heteroaromatic rings in a context other than nucleic acids
    • McKay S.L., Haptonstall B., Gellman S.H. Beyond the hydrophobic effect: attractions involving heteroaromatic rings in aqueous solution. J Am Chem Soc. 123:2001;1244-1245. This paper provides the only example of the stacking of heteroaromatic rings in a context other than nucleic acids.
    • (2001) J Am Chem Soc , vol.123 , pp. 1244-1245
    • McKay, S.L.1    Haptonstall, B.2    Gellman, S.H.3


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