Rapid Configuration Determination of Carbon-17Ethylene Bond in Natural Pregn-17(20)-ene

Abstract

Abstract:

The configuration of carbon-17 ethylene bond in pregn-17(20)-ene derivatives has important influence on the pharmacological properties of the compounds. However, the previously used methods for configuration determination of pregn-17(20)-ene derivatives either are time consuming or cannot obtain certain results. In this paper, we proposed to use 1D selective NOESY to determine the configuration of carbon-17 ethylene bond in E- and Z-guggulsterone. The results showed that, by selective inversion of H-20, the NOE spectra of E-guggulsterone showed only the signal from H-21, while that of Z-guggulsterone showed additional signals from H-18 and H-12. Our results indicated that the selective NOE experiment is a rapid and simple method for configuration determination of the carbon-17 ethylene bond in pregnanes.

Key words: NMR, configuration, selective NOESY, pregn-17(20)-ene

CLC Number:

O482.53

JIANG Hai-Peng, JIANG Xian-Wang, ZHANG Xu, LIU Mai-Li. Rapid Configuration Determination of Carbon-17Ethylene Bond in Natural Pregn-17(20)-ene[J]. Chinese Journal of Magnetic Resonance, 2011, 28(1): 93-98.

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