| Is (9Z)-"meso"-zeaxanthin optically active? | |
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MedLine Citation:
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PMID: 11284028 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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The question raised in the title was answered. (3R, 3'S)-meso-Zeaxanthin was submitted to iodine catalyzed photochemical stereoisomerisation. The enantiomeric (9Z) and (9'Z) geometrical isomers were isolated by semipreparative HPLC and separated as diastereomeric dicarbamates on a chiral column only. Cleavage of the carbamate could not be effected. CD-Spectra of (1"S, 1"S)- and (1"R, 1"R)-dicarbamates of geometrical isomers of (3R, 3'R)- and (3R, 3'S)-meso-zeaxanthin were systematically studied and the contribution from the carbamate moieties revealed. It was concluded that (9Z, 3R, 3'S)-"meso"-zeaxanthin, in spite of having no symmetry elements, is optically inactive. The result has been rationalised in line with the current hypothesis on the origin of carotenoid CD spectra. |
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Authors:
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B F Lutnaes; O R Gautun; S Liaaen-Jensen |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Chirality Volume: 13 ISSN: 0899-0042 ISO Abbreviation: Chirality Publication Date: 2001 May |
Date Detail:
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Created Date: 2001-04-03 Completed Date: 2001-07-19 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 8914261 Medline TA: Chirality Country: United States |
Other Details:
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Languages: eng Pagination: 224-9 Citation Subset: IM |
Affiliation:
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Organic Chemistry Laboratories, Faculty of Chemistry and Biology, Norwegian University of Science and Technology (NTNU), NO-7491 Trondheim, Norway. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Chromatography, High Pressure Liquid Circular Dichroism Stereoisomerism Xanthophylls beta Carotene / analogs & derivatives, chemistry*, isolation & purification |
| Chemical | |
Reg. No./Substance:
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0/Xanthophylls; 144-68-3/zeaxanthin; 7235-40-7/beta Carotene |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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