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Structure and conformation of α-, β- and γ-cyclodextrin in solution: theoretical approaches and experimental validation

Tafazzoli, M ; Sharif University of Technology | 2009

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  1. Type of Document: Article
  2. DOI: 10.1016/j.carbpol.2009.02.020
  3. Publisher: 2009
  4. Abstract:
  5. The anomeric carbon chemical shifts of α-, β- and γ-cyclodextrin in solution were studied experimentally and theoretically by NMR and two-layer ONIOM2 (B3LYP/6-31G*-GIAO: HF/6-31G*-GIAO) variant. The dependence between the anomeric carbon chemical shift and the glycosidic bond φ and ψ dihedral angles in d-Glcp-d-Glcp disaccharides with and (1 → 4) linkages in α-configurations were computed by Gauge-Including Atomic Orbital (GIAO) ab initio and ONIOM in water solvent using PCM methods. Complete chemical shift surfaces versus φ and ψ for this disaccharide were computed. We also present empirical formulas of the form 13C δ = f(φ, ψ) obtained by fitting the ab initio data to trigonometric series expansions. The results are consistent with experimental observations and show the applicability of chemical shift surfaces in the conformational behavior of oligosaccharides. © 2009 Elsevier Ltd. All rights reserved
  6. Keywords:
  7. 13C NMR chemical shift surface ; Cyclodextrin ; Anomeric carbon ; GIAO ; Glycosidic bond ; ONIOM methods ; Chemical shift ; Fourier series ; Nuclear magnetic resonance ; Nuclear magnetic resonance spectroscopy ; Polysaccharides ; Conformations
  8. Source: Carbohydrate Polymers ; Volume 78, Issue 1 , 2009 , Pages 10-15 ; 01448617 (ISSN)
  9. URL: https://www.sciencedirect.com/science/article/abs/pii/S014486170900109X