Synthesis of CD3-labeled 11-cis-retinals and application to solid-state deuterium NMR spectroscopy of rhodopsin

Katsunori Tanaka, Andrey V. Struts, Sonja Krane, Naoko Fujioka, Gilmar F.J. Salgado, Karina Martínez-Mayorga, Michael F. Brown, Koji Nakanishi

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11 Scopus citations

Abstract

Efficient synthesis of 11-Z-retinals labeled with 2H at the C5, C9, or C13 methyl groups is described. The 2H-labeled retinals were used to regenerate the visual pigment rhodopsin for structural investigations. Solid-state 2H NMR data provided the orientation of retinal within the rhodopsin binding pocket as well as its conformation. Extension of the approach to other membrane receptors can yield knowledge of their mechanisms of activation as a guide for ligand-based drug design.

Original languageEnglish (US)
Pages (from-to)2177-2184
Number of pages8
JournalBulletin of the Chemical Society of Japan
Volume80
Issue number11
DOIs
StatePublished - Dec 1 2007

ASJC Scopus subject areas

  • Chemistry(all)

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    Tanaka, K., Struts, A. V., Krane, S., Fujioka, N., Salgado, G. F. J., Martínez-Mayorga, K., Brown, M. F., & Nakanishi, K. (2007). Synthesis of CD3-labeled 11-cis-retinals and application to solid-state deuterium NMR spectroscopy of rhodopsin. Bulletin of the Chemical Society of Japan, 80(11), 2177-2184. https://doi.org/10.1246/bcsj.80.2177