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Governing parameters of long-range intramolecular S-to-N acyl transfers within (S)-acyl isopeptides

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Abstract
The governing parameters for the long-range intramolecular S-to-N acyl transfer in (S)-acyl isopeptides are shown by computational and statistical methods (principal component analysis and cluster analysis) to be driven by enthalpic and geometric effects over the range n = 5-20. The results emphasize the dependency of Delta G double dagger on the geometrical parameters governing the approach of the reactive termini and the importance of stabilizing intramolecular hydrogen bonds in the transition states (TSs), rather than the effects of TS ring-size. The competition between the intra- (uni-) and inter- (bi)molecular acyl transfers were studied for representative examples.
Keywords
BIFUNCTIONAL CHAIN MOLECULES, RING-CLOSURE REACTIONS, CYCLIC ANHYDRIDE FORMATION, SUGAR-ASSISTED LIGATION, PHASE PEPTIDE-SYNTHESIS, ENZYMATIC-REACTIONS, CHEMICAL-SYNTHESIS, TRANSITION-STATES, GROUND-STATE, DIFFICULT SEQUENCE

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MLA
Monbaliu, Jean-Christophe et al. “Governing Parameters of Long-range Intramolecular S-to-N Acyl Transfers Within (S)-acyl Isopeptides.” JOURNAL OF CHEMICAL THEORY AND COMPUTATION 9.2 (2013): 927–934. Print.
APA
Monbaliu, J.-C., Dive, G., Stevens, C., & Katritzky, A. R. (2013). Governing parameters of long-range intramolecular S-to-N acyl transfers within (S)-acyl isopeptides. JOURNAL OF CHEMICAL THEORY AND COMPUTATION, 9(2), 927–934.
Chicago author-date
Monbaliu, Jean-Christophe, Georges Dive, Christian Stevens, and Alan R Katritzky. 2013. “Governing Parameters of Long-range Intramolecular S-to-N Acyl Transfers Within (S)-acyl Isopeptides.” Journal of Chemical Theory and Computation 9 (2): 927–934.
Chicago author-date (all authors)
Monbaliu, Jean-Christophe, Georges Dive, Christian Stevens, and Alan R Katritzky. 2013. “Governing Parameters of Long-range Intramolecular S-to-N Acyl Transfers Within (S)-acyl Isopeptides.” Journal of Chemical Theory and Computation 9 (2): 927–934.
Vancouver
1.
Monbaliu J-C, Dive G, Stevens C, Katritzky AR. Governing parameters of long-range intramolecular S-to-N acyl transfers within (S)-acyl isopeptides. JOURNAL OF CHEMICAL THEORY AND COMPUTATION. 2013;9(2):927–34.
IEEE
[1]
J.-C. Monbaliu, G. Dive, C. Stevens, and A. R. Katritzky, “Governing parameters of long-range intramolecular S-to-N acyl transfers within (S)-acyl isopeptides,” JOURNAL OF CHEMICAL THEORY AND COMPUTATION, vol. 9, no. 2, pp. 927–934, 2013.
@article{8057373,
  abstract     = {The governing parameters for the long-range intramolecular S-to-N acyl transfer in (S)-acyl isopeptides are shown by computational and statistical methods (principal component analysis and cluster analysis) to be driven by enthalpic and geometric effects over the range n = 5-20. The results emphasize the dependency of Delta G double dagger on the geometrical parameters governing the approach of the reactive termini and the importance of stabilizing intramolecular hydrogen bonds in the transition states (TSs), rather than the effects of TS ring-size. The competition between the intra- (uni-) and inter- (bi)molecular acyl transfers were studied for representative examples.},
  author       = {Monbaliu, Jean-Christophe and Dive, Georges and Stevens, Christian and Katritzky, Alan R},
  issn         = {1549-9618},
  journal      = {JOURNAL OF CHEMICAL THEORY AND COMPUTATION},
  keywords     = {BIFUNCTIONAL CHAIN MOLECULES,RING-CLOSURE REACTIONS,CYCLIC ANHYDRIDE FORMATION,SUGAR-ASSISTED LIGATION,PHASE PEPTIDE-SYNTHESIS,ENZYMATIC-REACTIONS,CHEMICAL-SYNTHESIS,TRANSITION-STATES,GROUND-STATE,DIFFICULT SEQUENCE},
  language     = {eng},
  number       = {2},
  pages        = {927--934},
  title        = {Governing parameters of long-range intramolecular S-to-N acyl transfers within (S)-acyl isopeptides},
  url          = {http://dx.doi.org/10.1021/ct300830k},
  volume       = {9},
  year         = {2013},
}

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