Long-range proton–carbon coupling constants for the determination of the stereochemical structure of organic compounds.
Keywords:
HSQC-TOCSY, J-coupling, 2D NMR
Abstract
A new methods for elucidating stereochemistry of organic compounds was developed on the basis of long-range proton–carbon coupling constants (2,3JC,H) and interpreting spin-coupling constants (3JH,H). Reaction of compound containing pyrin ring with nucleophile reagent was done to open the ring. HSQC-TOCSY experiments one of the new NMR spectroscopy method used to measure this values of spin-coupling constants and elucidating the stereochemistry of the product.
References
Goffin, D.; Bystricky, P., Shashkov, A. S., Lynch, M., Hanon, E., Paquot, M. and Savage, A. V.; (2009); A Systematic NMR Determination of α-D-Glucooligosaccharides, Effect of Linkage Type, Anomeric Configuration and Combination of Different Linkages Type on 13C Chemical Shifts for the Determination of Unknown Isomaltooligosaccharides; Bull. Korean Chem. Soc. Vol. 30, No. 11 2535
Ludwig, C and Viant, M. R.; (2010); Two-dimensional J-resolved NMR Spectroscopy: Review of a Key Methodology in the Metabolomics Toolbox; Phytochem. Anal.; 21; 22–32.
Matsumori, N., Kaneno, D., Murata, M., Nakamura, H. and Tachibana, K.; (1999); Stereochemical Determination of Acyclic Structures Based on Carbon-Proton Spin-Coupling Constants. A Method of Configuration Analysis for Natural Products.; J. Org. Chem.; 64, 866-876
Nolis, P. and Parella, T.; (2005); Spin-edited 2D HSQC–TOCSY experiments for the measurement of homonuclear and heteronuclear coupling constants: Application to carbohydrates and peptides; Journal of Magnetic Resonance 176 15–26
Parella, T. and Espinosa, J. F.; (2013) ; Long-range proton–carbon coupling constants: NMR methods and applications; Progress in Nuclear Magnetic Resonance Spectroscopy; 73; 17–55
Ludwig, C and Viant, M. R.; (2010); Two-dimensional J-resolved NMR Spectroscopy: Review of a Key Methodology in the Metabolomics Toolbox; Phytochem. Anal.; 21; 22–32.
Matsumori, N., Kaneno, D., Murata, M., Nakamura, H. and Tachibana, K.; (1999); Stereochemical Determination of Acyclic Structures Based on Carbon-Proton Spin-Coupling Constants. A Method of Configuration Analysis for Natural Products.; J. Org. Chem.; 64, 866-876
Nolis, P. and Parella, T.; (2005); Spin-edited 2D HSQC–TOCSY experiments for the measurement of homonuclear and heteronuclear coupling constants: Application to carbohydrates and peptides; Journal of Magnetic Resonance 176 15–26
Parella, T. and Espinosa, J. F.; (2013) ; Long-range proton–carbon coupling constants: NMR methods and applications; Progress in Nuclear Magnetic Resonance Spectroscopy; 73; 17–55
Published
2021-08-17
How to Cite
Anwar, E. M. Noreljaleel. (2021). Long-range proton–carbon coupling constants for the determination of the stereochemical structure of organic compounds. Journal of The Faculty of Science and Technology, (7), 125 - 131. https://doi.org/10.52981/jfst.vi7.965
Section
Articles
