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C-13 NMR spectra of all-trans-N-retinylidene-n-butylamine as an analogue of the Schiff base linkage compound in visual pigment

Journal Article:

Abstract

In the process of visual excitation, a visual pigment, rhodopsin, plays a role of a photoreceptor, and it has been known that the first step in the process is the photoisomerization of the rhodopsin visual chromophore. The bathochromic shift has been regarded as the result of the formation of Schiff base linkage of retinal with opsin. In this study, C-13 NMR spectra were obtained for the analogue of the compound with Schiff base linkage in the visual pigment, and the chemical shift change for going from all trans-retinal to all trans-N-retinylidene-n-butylamine (NRB) was discussed. Further, the effect of N protonation in NRB was examined as the reflection of the function of visual pigment. The compound with Schiff base linkage of all trans-retinal with n-butylamine, namely NRB, was used. The nuclear magnetic resonance (NMR) spectra of carbon-13 Fourier transformation were obtained for this sample at natural abundance with a JNM PS-100 spectrometer. In the C-13 FT NMR spectrum of NRB, besides eight peaks in the C-13 NMR of all trans-retinal, four peaks were observed in higher field region. They originated from the portion of n-butylamine in the compound with Schiff base linkage. The peaks in lower field region were assigned to  More>>
Authors:
Tokito, Y; Inoue, Y; Chujo, R; [1]  Miyoshi, Y
  1. Tokyo Inst. of Tech. (Japan). Faculty of Science
Publication Date:
Jan 01, 1975
Product Type:
Journal Article
Reference Number:
AIX-07-266551; EDB-77-007533
Resource Relation:
Journal Name: Rep. Prog. Polym. Phys. Jpn.; (Japan); Journal Volume: 18
Subject:
37 INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY; AMINES; ELECTRONIC STRUCTURE; CARBON 13; NUCLEAR MAGNETIC RESONANCE; PIGMENTS; VISION; CHEMICAL BONDS; CHEMICAL SHIFT; ELECTRONS; POLYENES; SCHIFF BASES; SPIN-LATTICE RELAXATION; CARBON ISOTOPES; ELEMENTARY PARTICLES; EVEN-ODD NUCLEI; FERMIONS; HYDROCARBONS; IMINES; ISOTOPES; LEPTONS; LIGHT NUCLEI; MAGNETIC RESONANCE; NUCLEI; ORGANIC COMPOUNDS; ORGANIC NITROGEN COMPOUNDS; RELAXATION; RESONANCE; STABLE ISOTOPES; 400301* - Organic Chemistry- Chemical & Physicochemical Properties- (-1987)
OSTI ID:
7142532
Country of Origin:
Japan
Language:
English
Other Identifying Numbers:
Journal ID: CODEN: RPPJA
Submitting Site:
INIS
Size:
Pages: 645-648
Announcement Date:
Nov 01, 1976

Journal Article:

Citation Formats

Tokito, Y, Inoue, Y, Chujo, R, and Miyoshi, Y. C-13 NMR spectra of all-trans-N-retinylidene-n-butylamine as an analogue of the Schiff base linkage compound in visual pigment. Japan: N. p., 1975. Web.
Tokito, Y, Inoue, Y, Chujo, R, & Miyoshi, Y. C-13 NMR spectra of all-trans-N-retinylidene-n-butylamine as an analogue of the Schiff base linkage compound in visual pigment. Japan.
Tokito, Y, Inoue, Y, Chujo, R, and Miyoshi, Y. 1975. "C-13 NMR spectra of all-trans-N-retinylidene-n-butylamine as an analogue of the Schiff base linkage compound in visual pigment." Japan.
@misc{etde_7142532,
title = {C-13 NMR spectra of all-trans-N-retinylidene-n-butylamine as an analogue of the Schiff base linkage compound in visual pigment}
author = {Tokito, Y, Inoue, Y, Chujo, R, and Miyoshi, Y}
abstractNote = {In the process of visual excitation, a visual pigment, rhodopsin, plays a role of a photoreceptor, and it has been known that the first step in the process is the photoisomerization of the rhodopsin visual chromophore. The bathochromic shift has been regarded as the result of the formation of Schiff base linkage of retinal with opsin. In this study, C-13 NMR spectra were obtained for the analogue of the compound with Schiff base linkage in the visual pigment, and the chemical shift change for going from all trans-retinal to all trans-N-retinylidene-n-butylamine (NRB) was discussed. Further, the effect of N protonation in NRB was examined as the reflection of the function of visual pigment. The compound with Schiff base linkage of all trans-retinal with n-butylamine, namely NRB, was used. The nuclear magnetic resonance (NMR) spectra of carbon-13 Fourier transformation were obtained for this sample at natural abundance with a JNM PS-100 spectrometer. In the C-13 FT NMR spectrum of NRB, besides eight peaks in the C-13 NMR of all trans-retinal, four peaks were observed in higher field region. They originated from the portion of n-butylamine in the compound with Schiff base linkage. The peaks in lower field region were assigned to eleven conjugated polyene carbons by the measurement of spin-lattice relaxation time and shift. The chemical shift change for going from retinal to NRB is shown. It is concluded that the ..pi..-electrons in polyene chains are considerably delocalized by the collapse of bond alteration in the retinal forming Schiff base linkage.}
journal = {Rep. Prog. Polym. Phys. Jpn.; (Japan)}
volume = {18}
journal type = {AC}
place = {Japan}
year = {1975}
month = {Jan}
}