The mechanism of the colour shift of astaxanthin in alpha-crustacyanin as investigated by C-13 MAS NMR and specific isotope enrichment
By selective isotope enrichment of astaxanthin, MAS NMR and semi-empirical modelling, ligand-protein interactions associated with the red shift in alpha-crustacyanin, the major blue astaxanthin binding carotenoprotein complex from the carapace of the lobster Homarus gammarus, have been analysed. C-1...
Published in: | Pure and Applied Chemistry |
---|---|
Main Authors: | , , , , , |
Format: | Article in Journal/Newspaper |
Language: | English |
Published: |
1997
|
Subjects: | |
Online Access: | https://hdl.handle.net/1887/3238825 https://www.degruyter.com/document/doi/10.1351/pac199769102085/html https://doi.org/10.1351/pac199769102085 |
id |
ftunivleiden:oai:scholarlypublications.universiteitleiden.nl:item_3238825 |
---|---|
record_format |
openpolar |
spelling |
ftunivleiden:oai:scholarlypublications.universiteitleiden.nl:item_3238825 2023-05-15T16:34:43+02:00 The mechanism of the colour shift of astaxanthin in alpha-crustacyanin as investigated by C-13 MAS NMR and specific isotope enrichment Weesie, R.J. Verel, R. Jansen, F.J.H.M. Britton, G. Lugtenburg, J. Groot, H.J.M. de 1997 https://hdl.handle.net/1887/3238825 https://www.degruyter.com/document/doi/10.1351/pac199769102085/html https://doi.org/10.1351/pac199769102085 en eng https://www.degruyter.com/document/doi/10.1351/pac199769102085/html doi:10.1351/pac199769102085 lucris-id: 429527919 https://hdl.handle.net/1887/3238825 https://hdl.handle.net/1887/license:4 Pure and Applied Chemistry Article / Letter to editor info:eu-repo/semantics/article Text 1997 ftunivleiden https://doi.org/10.1351/pac199769102085 2021-11-17T23:11:37Z By selective isotope enrichment of astaxanthin, MAS NMR and semi-empirical modelling, ligand-protein interactions associated with the red shift in alpha-crustacyanin, the major blue astaxanthin binding carotenoprotein complex from the carapace of the lobster Homarus gammarus, have been analysed. C-13 Magic Angle Spinning (MAS) NMR spectra were obtained after reconstitution with astaxanthins labelled in the centre of the molecule or at the two keto groups. The MAS data reveal electrostatic polarizations of the conjugated chain. In addition, solid state NMR results for pure unlabelled astaxanthin can be compared with natural abundance C-13 MAS data for canthaxanthin and beta-carotene, to address the effect of the ring functionalities on the electronic properties of the polyene chain. Quantum chemical calculations were performed to reconcile the MAS data with one of several simple and straightforward mechanisms for the colour shift. The results point towards a colour shift mechanism in which the astaxanthin may be doubly charged, possibly by a double protonation of the two ring keto groups. Bio-organic Synthesis Solid state NMR/Biophysical Organic Chemistry Article in Journal/Newspaper Homarus gammarus Leiden University Scholarly Publications Pure and Applied Chemistry 69 10 2085 2090 |
institution |
Open Polar |
collection |
Leiden University Scholarly Publications |
op_collection_id |
ftunivleiden |
language |
English |
description |
By selective isotope enrichment of astaxanthin, MAS NMR and semi-empirical modelling, ligand-protein interactions associated with the red shift in alpha-crustacyanin, the major blue astaxanthin binding carotenoprotein complex from the carapace of the lobster Homarus gammarus, have been analysed. C-13 Magic Angle Spinning (MAS) NMR spectra were obtained after reconstitution with astaxanthins labelled in the centre of the molecule or at the two keto groups. The MAS data reveal electrostatic polarizations of the conjugated chain. In addition, solid state NMR results for pure unlabelled astaxanthin can be compared with natural abundance C-13 MAS data for canthaxanthin and beta-carotene, to address the effect of the ring functionalities on the electronic properties of the polyene chain. Quantum chemical calculations were performed to reconcile the MAS data with one of several simple and straightforward mechanisms for the colour shift. The results point towards a colour shift mechanism in which the astaxanthin may be doubly charged, possibly by a double protonation of the two ring keto groups. Bio-organic Synthesis Solid state NMR/Biophysical Organic Chemistry |
format |
Article in Journal/Newspaper |
author |
Weesie, R.J. Verel, R. Jansen, F.J.H.M. Britton, G. Lugtenburg, J. Groot, H.J.M. de |
spellingShingle |
Weesie, R.J. Verel, R. Jansen, F.J.H.M. Britton, G. Lugtenburg, J. Groot, H.J.M. de The mechanism of the colour shift of astaxanthin in alpha-crustacyanin as investigated by C-13 MAS NMR and specific isotope enrichment |
author_facet |
Weesie, R.J. Verel, R. Jansen, F.J.H.M. Britton, G. Lugtenburg, J. Groot, H.J.M. de |
author_sort |
Weesie, R.J. |
title |
The mechanism of the colour shift of astaxanthin in alpha-crustacyanin as investigated by C-13 MAS NMR and specific isotope enrichment |
title_short |
The mechanism of the colour shift of astaxanthin in alpha-crustacyanin as investigated by C-13 MAS NMR and specific isotope enrichment |
title_full |
The mechanism of the colour shift of astaxanthin in alpha-crustacyanin as investigated by C-13 MAS NMR and specific isotope enrichment |
title_fullStr |
The mechanism of the colour shift of astaxanthin in alpha-crustacyanin as investigated by C-13 MAS NMR and specific isotope enrichment |
title_full_unstemmed |
The mechanism of the colour shift of astaxanthin in alpha-crustacyanin as investigated by C-13 MAS NMR and specific isotope enrichment |
title_sort |
mechanism of the colour shift of astaxanthin in alpha-crustacyanin as investigated by c-13 mas nmr and specific isotope enrichment |
publishDate |
1997 |
url |
https://hdl.handle.net/1887/3238825 https://www.degruyter.com/document/doi/10.1351/pac199769102085/html https://doi.org/10.1351/pac199769102085 |
genre |
Homarus gammarus |
genre_facet |
Homarus gammarus |
op_source |
Pure and Applied Chemistry |
op_relation |
https://www.degruyter.com/document/doi/10.1351/pac199769102085/html doi:10.1351/pac199769102085 lucris-id: 429527919 https://hdl.handle.net/1887/3238825 |
op_rights |
https://hdl.handle.net/1887/license:4 |
op_doi |
https://doi.org/10.1351/pac199769102085 |
container_title |
Pure and Applied Chemistry |
container_volume |
69 |
container_issue |
10 |
container_start_page |
2085 |
op_container_end_page |
2090 |
_version_ |
1766024700284108800 |