Loading...

Dynamic stereochemistry of erigeroside by measurement of 1H-1H and 13C-1H coupling constants

Tafazzoli, M ; Sharif University of Technology | 2008

431 Viewed
  1. Type of Document: Article
  2. DOI: 10.1016/j.saa.2007.10.033
  3. Publisher: 2008
  4. Abstract:
  5. Erigeroside was extracted from Satureja khuzistanica Jamzad (Marzeh Khuzistani in Persian, family of lamiaceae), and 1H, 13C, 13C{1H}, 1H-1H COSY, HMQC and J-HMBC were obtained to identify this compound and determine a complete set of J-coupling constants (1JC-H, 2JC-H, 3JC-H and 3JH-H) values within the exocyclic hydroxymethyl group (CH2OH) and anomeric center. In parallel, density functional theory (DFT) using B3LYP functional and split-valance 6-311++G** basis set has been used to optimized the structures and conformers of erigeroside. In all calculations solvent effects were considered using a polarized continuum (overlapping spheres) model (PCM). The dependencies of 1J, 2J and 3J involving 1H and 13C on the C5′-C6′ (ω), C6′-O6′ (θ) and C1′-O1′ (φ) torsion angles in erigeroside were computed using DFT method. Complete hyper surfaces for 1JC1′,H1′, 2JC5′,H6′R, 2JC5′,H6′S, 2JC6′,H5′, 3JC4′,H6′R, 3JC4′,H6′S and 2JH6′R-H5′S as well as 3JH5′,H6′R were obtained and used to derive Karplus equations to correlate these couplings to ω, θ and φ. These calculated J-couplings are in agreement with experimental values. These results confirm the reliability of DFT calculated coupling constants in aqueous solution. © 2007 Elsevier B.V. All rights reserved
  6. Keywords:
  7. Density functional theory ; Functional groups ; Molecular structure ; Problem solving ; Stereochemistry ; Coupling constants ; Erigeroside ; Hydroxymethyl group ; Solvent effects ; Coupling agents ; erigeroside ; Pyrone derivative ; Chemistry ; Conformation ; Nuclear magnetic resonance ; Stereoisomerism ; Molecular Conformation ; Nuclear Magnetic Resonance, Biomolecular ; Pyrones ; Stereoisomerism
  8. Source: Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy ; Volume 70, Issue 2 , 2008 , Pages 350-357 ; 13861425 (ISSN)
  9. URL: https://www.sciencedirect.com/science/article/abs/pii/S1386142507005860