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Volumn 125, Issue 8, 2003, Pages 2094-2100

Tandem electrostatic effect from the first to the third aglycon in the trimeric RNA owing to the nearest-neighbor interaction

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PSEUDOAROMATICITY;

EID: 0037466990     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja028277h     Document Type: Article
Times cited : (15)

References (67)
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    • The importance of stacking has been identified in DNA polymerase activity and in efficiency of DNA synthesis. For review: Kool, E. T. Annu. Rev. Biophys. Biomol. Struct. 2001, 30, 1, and references therein.
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  • 17
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    • The interaction of the aromatic rings depends on the stacking geometry: edge-to-face, (ii) offset stacked, and (iii) face-to-face stacked. The offset stacked arrangement minimizes π-electron repulsion and maximizes the interactions in the σ-framework. For review: Hunter, C. A.; Lawson, K. R.; Perkins, J.; Urch, C. J. J. Chem. Soc., Perkin Trans. 2 2001, 651.
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    • and refs 1, 2, and 8 therein
    • The experimental evidence showed that the magnitude of offset-stacking interactions can be dictated by the geometry of the stacked components, which, in turn, is influenced by the nature of ring substituents. Rashkin, M. J.; Waters, M. L. J. Am. Chem. Soc. 2002, 124, 1860 and refs 1, 2, and 8 therein. (b) Newcomb, L. F.; Gellman, S. H. Am. Chem. Soc. 1994, 116, 4993. (c) Kim, E.; Paliwal, S.; Wilcox, C. S. J. Am. Chem. Soc. 1998, 120, 11 192. (d) Jennings, W. B.; Farrell, B. M.; Malone, J. F. Acc. Chem. Res. 2001, 34, 885. (e) Carver, F. J.; Hunter, C. A.; Seward, E. M. J. Chem. Soc., Chem. Commun. 1998, 775.
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  • 19
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    • The experimental evidence showed that the magnitude of offset-stacking interactions can be dictated by the geometry of the stacked components, which, in turn, is influenced by the nature of ring substituents. Rashkin, M. J.; Waters, M. L. J. Am. Chem. Soc. 2002, 124, 1860 and refs 1, 2, and 8 therein. (b) Newcomb, L. F.; Gellman, S. H. Am. Chem. Soc. 1994, 116, 4993. (c) Kim, E.; Paliwal, S.; Wilcox, C. S. J. Am. Chem. Soc. 1998, 120, 11 192. (d) Jennings, W. B.; Farrell, B. M.; Malone, J. F. Acc. Chem. Res. 2001, 34, 885. (e) Carver, F. J.; Hunter, C. A.; Seward, E. M. J. Chem. Soc., Chem. Commun. 1998, 775.
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  • 20
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    • The experimental evidence showed that the magnitude of offset-stacking interactions can be dictated by the geometry of the stacked components, which, in turn, is influenced by the nature of ring substituents. Rashkin, M. J.; Waters, M. L. J. Am. Chem. Soc. 2002, 124, 1860 and refs 1, 2, and 8 therein. (b) Newcomb, L. F.; Gellman, S. H. Am. Chem. Soc. 1994, 116, 4993. (c) Kim, E.; Paliwal, S.; Wilcox, C. S. J. Am. Chem. Soc. 1998, 120, 11 192. (d) Jennings, W. B.; Farrell, B. M.; Malone, J. F. Acc. Chem. Res. 2001, 34, 885. (e) Carver, F. J.; Hunter, C. A.; Seward, E. M. J. Chem. Soc., Chem. Commun. 1998, 775.
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  • 21
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    • The experimental evidence showed that the magnitude of offset-stacking interactions can be dictated by the geometry of the stacked components, which, in turn, is influenced by the nature of ring substituents. Rashkin, M. J.; Waters, M. L. J. Am. Chem. Soc. 2002, 124, 1860 and refs 1, 2, and 8 therein. (b) Newcomb, L. F.; Gellman, S. H. Am. Chem. Soc. 1994, 116, 4993. (c) Kim, E.; Paliwal, S.; Wilcox, C. S. J. Am. Chem. Soc. 1998, 120, 11 192. (d) Jennings, W. B.; Farrell, B. M.; Malone, J. F. Acc. Chem. Res. 2001, 34, 885. (e) Carver, F. J.; Hunter, C. A.; Seward, E. M. J. Chem. Soc., Chem. Commun. 1998, 775.
    • (2001) Acc. Chem. Res. , vol.34 , pp. 885
    • Jennings, W.B.1    Farrell, B.M.2    Malone, J.F.3
  • 22
    • 0001660487 scopus 로고    scopus 로고
    • The experimental evidence showed that the magnitude of offset-stacking interactions can be dictated by the geometry of the stacked components, which, in turn, is influenced by the nature of ring substituents. Rashkin, M. J.; Waters, M. L. J. Am. Chem. Soc. 2002, 124, 1860 and refs 1, 2, and 8 therein. (b) Newcomb, L. F.; Gellman, S. H. Am. Chem. Soc. 1994, 116, 4993. (c) Kim, E.; Paliwal, S.; Wilcox, C. S. J. Am. Chem. Soc. 1998, 120, 11 192. (d) Jennings, W. B.; Farrell, B. M.; Malone, J. F. Acc. Chem. Res. 2001, 34, 885. (e) Carver, F. J.; Hunter, C. A.; Seward, E. M. J. Chem. Soc., Chem. Commun. 1998, 775.
    • (1998) J. Chem. Soc., Chem. Commun. , pp. 775
    • Carver, F.J.1    Hunter, C.A.2    Seward, E.M.3
  • 25
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    • note
    • a for compounds 1-4. See ref 20 for the details of the theoretical basis of abovementioned equation.
  • 57
    • 0013350805 scopus 로고    scopus 로고
    • note
    • H8A(pAp) of 0.12 ppm at the N state and 0.124 ppm in D state.
  • 58
    • 0013440895 scopus 로고    scopus 로고
    • note
    • N-D: -0.069.
  • 59
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    • note
    • pKa found is owing to slight changes in the microenvironment of the dimer and as well as the electronic properties trimers with respect to the monomer (see also ref 25).
  • 60
    • 0013394731 scopus 로고    scopus 로고
    • note
    • 1p shows a detectable upfield shift over the pH range. Thus, the different pH-dependent tunibility of δH8 and δH2 of adenin-9-yl in pA and pAp, indicates the sequence-dependency owing to differential modulation of the pseudoaromatic character of adenine-9-yl in 2-4 by the effect of the nearest-neighbor.
  • 61
    • 0013349648 scopus 로고    scopus 로고
    • note
    • 8,10 to pAp to experience the differential electrostatic interaction from the 5′terminal guanylate to minimize the Coulombic repulsion in GpApA (3). In contrast, the pAp in GpApC (4) is "offset stacked" such that imidazole part of pAp is within the influence of π-electron system of the guanylate anion, whereas the C5-C6 double bond of pC is also "offset stacked" with respect to pAp.
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    • note
    • 8,10 which means that the imidazole edge of adenin-9-yl is within the stacking interaction of 9-guaninyl face.
  • 67
    • 0013352521 scopus 로고    scopus 로고
    • note
    • a unit on the terminal guanin-9-yl in Gp in our case) upon an increase of the total number of phosphates in the molecule as a result of chain elongation.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.