✦ LIBER ✦

Synthesis and NMR spectrum of [13C18]-meso-hexestrol, a fully carbon-13 substituted ligand for NMR studies of the estrogen receptor

✍ Scribed by Monica J. Kochanny; Torleif Härd; John A. Katzenellenbogen

Publisher: John Wiley and Sons
Year: 1993
Tongue: English
Weight: 898 KB
Volume: 31
Category: Article
ISSN: 0749-1581
DOI: 10.1002/mrc.1260311105

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✦ Synopsis

Abstract

The estrogen receptor ligand meso‐hexestrol has been synthesized with ^13^C enrichment (98 at.%) at every position. ^13^C NMR spectra of the intermediates were obtained and ^13^C−^13^C coupling patterns analyzed. The complex ^13^C NMR spectrum of [^13^C~18~]‐meso‐hexestrol was simplified through the use of selective ^13^C decoupling. Several ^13^C−^13^C coupling constants were estimated from the decoupled spectra and refined via iterative simulation. Some additional coupling constants were measured in selective one‐dimensional ^13^C COSY spectra. Coupling constants are reported to an accuracy of ±0.4–1 Hz. This study demonstrates the feasibility of determining ^13^C−^13^C coupling constants in highly ^13^C−substituted compounds; such compounds are expected to be used with increased frequency in studying receptor‐ligand interactions by polarization transfer methods.

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