Measurement of long range H,C couplings in natural products in orienting media: a tool for structure elucidation of natural products

J Magn Reson. 2003 Aug;163(2):353-9. doi: 10.1016/s1090-7807(03)00063-6.

Abstract

In this paper we show that water insoluble compounds dissolved in poly-gamma-benzyl-glutamate are amenable to the measurement of a number of homo- and heteronuclear dipolar couplings. The sensitivity and experimental precision of dipolar couplings are sufficient to obtain a good match with the structure. In order to achieve the necessary precision for H,C dipolar couplings between protons and carbons that are not directly bound a new method for the measurement of heteronuclear long range couplings is introduced that allows a one-parameter fit to a HSQC-based experiment as reference experiment. The methodology is applied to menthol (1R, 3S, 4R).

Publication types

  • Comparative Study
  • Evaluation Study
  • Research Support, Non-U.S. Gov't
  • Validation Study

MeSH terms

  • Carbon / chemistry*
  • Crystallization / methods
  • Crystallography / methods*
  • Hydrogen / chemistry*
  • Hydrogen Bonding
  • Menthol / chemistry*
  • Molecular Conformation
  • Nuclear Magnetic Resonance, Biomolecular / methods*
  • Polyglutamic Acid / analogs & derivatives*
  • Polyglutamic Acid / chemistry*
  • Reproducibility of Results
  • Sensitivity and Specificity
  • Solubility
  • Solutions / chemistry

Substances

  • Solutions
  • Menthol
  • poly-gamma-benzyl-L-glutamate
  • Polyglutamic Acid
  • Carbon
  • Hydrogen