Electronic spectra of carotenoids: A theoretical analysis of the electronic spectrum of rhodopinal

Chin, Chen-An; Song, Pill‐Soon

doi:10.1016/0022-2852(74)90112-x

Cited by 9 publications

(1 citation statement)

References 3 publications

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“…Previous studies have proposed that rhodopinal acquires a cis configuration in solution. 19,71−73 Based on density functional theory and an analysis of the absorption spectra, it is demonstrated here that rhodopinal takes on a cis configuration in both nonpolar and polar solvent. The all-trans rhodopinal chromophore exhibits just one significant intramolecular repulsion involving the interaction of the aldehyde hydrogen with the nearest hydrogen atom on the main polyene chain.…”

Section: Discussionmentioning

confidence: 98%

High Efficiency Light Harvesting by Carotenoids in the LH2 Complex from Photosynthetic Bacteria: Unique Adaptation to Growth under Low-Light Conditions

et al. 2014

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Rhodopin, rhodopinal, and their glucoside derivatives are carotenoids that accumulate in different amounts in the photosynthetic bacterium, Rhodoblastus (Rbl.) acidophilus strain 7050, depending on the intensity of the light under which the organism is grown. The different growth conditions also have a profound effect on the spectra of the bacteriochlorophyll (BChl) pigments that assemble in the major LH2 light-harvesting pigment–protein complex. Under high-light conditions the well-characterized B800-850 LH2 complex is formed and accumulates rhodopin and rhodopin glucoside as the primary carotenoids. Under low-light conditions, a variant LH2, denoted B800-820, is formed, and rhodopinal and rhodopinal glucoside are the most abundant carotenoids. The present investigation compares and contrasts the spectral properties and dynamics of the excited states of rhodopin and rhodopinal in solution. In addition, the systematic differences in pigment composition and structure of the chromophores in the LH2 complexes provide an opportunity to explore the effect of these factors on the rate and efficiency of carotenoid-to-BChl energy transfer. It is found that the enzymatic conversion of rhodopin to rhodopinal by Rbl. acidophilus 7050 grown under low-light conditions results in nearly 100% carotenoid-to-BChl energy transfer efficiency in the LH2 complex. This comparative analysis provides insight into how photosynthetic systems are able to adapt and survive under challenging environmental conditions.

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Section: Discussionmentioning

confidence: 98%

High Efficiency Light Harvesting by Carotenoids in the LH2 Complex from Photosynthetic Bacteria: Unique Adaptation to Growth under Low-Light Conditions

et al. 2014

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ChemInform Abstract: ELECTRONIC SPECTRA OF CAROTENOIDS, A THEORETICAL ANALYSIS OF THE ELECTRONIC SPECTRUM OF RHODOPINAL, SCHIFF′S BASES OF CAROTENAL AND CAROTENONES

Chin¹,

Song²,

Moore³

1974

Chemischer Informationsdienst

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Configuration of cross‐conjugated caroten‐20‐als: 2D NMR study on four isomers of renierapurpurin‐20‐al

Englert

Glinz

Liaaen‐Jensen

1988

Magnetic Reson in Chemistry

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The 400 MHz 'H NMR spectra of four cis isomers of synthetic renierapurpurin-20-al (X,X-caroten-ZQal) were completely assigned by application of two-dimensional protoeproton chemical shift correlated spectroscopy (2D COSY) with high digital resolution of ca 0.4 Hz per point by acquisition of only the olefinic part of the spectra. Connectivities to the methyl and aldehyde protons absorbing outside the measured range were also obtained owing to the folding of their cross-peaks along the F, axis. Nuclear Overhauser difference experiments and consideration of chemical shift changes were applied to derive unequivocally the 134s (13E), 7,13-di-cis (723 13,7'-di-cis (7'2) and 13,9'-di-cis (9'2) configuration of the isomers. The 'H-detected one-bond 'J(CH) and long-range '*'J(CH) multiple quantum coherence heterocorrelated 2D spectra of 1.2 mg of the main 13-cis isomer were acquired and the "C signals partly assigned. The structural consequences with respect to other cross-conjugated caroten-20-als are discussed.

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Electronic spectra of carotenoids: A theoretical analysis of the electronic spectrum of rhodopinal

Cited by 9 publications

References 3 publications

High Efficiency Light Harvesting by Carotenoids in the LH2 Complex from Photosynthetic Bacteria: Unique Adaptation to Growth under Low-Light Conditions

High Efficiency Light Harvesting by Carotenoids in the LH2 Complex from Photosynthetic Bacteria: Unique Adaptation to Growth under Low-Light Conditions

ChemInform Abstract: ELECTRONIC SPECTRA OF CAROTENOIDS, A THEORETICAL ANALYSIS OF THE ELECTRONIC SPECTRUM OF RHODOPINAL, SCHIFF′S BASES OF CAROTENAL AND CAROTENONES

Configuration of cross‐conjugated caroten‐20‐als: 2D NMR study on four isomers of renierapurpurin‐20‐al

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