101468-86-4Relevant articles and documents
METHODS FOR PREPARATION OF LYCOPENES FROM C15-WITTIG SALTS AND METHODS FOR PURIFICATION OF HIGH ALL-E CONTAINING AND HIGH 6Z CONTAINING C15-WITTIG SALTS
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Paragraph 0029, (2016/02/10)
The present invention relates to methods for preparation of lycopenes, especially to lycopenes with high all-E contents or high 6Z contents from C15-Wittig slats mixtures. (with high all-E-contents and high 6Z-contents, respectively). C15-Wittig slats mixtures are purified and 6Z-C15-Wittig salts are extracted from the mixtures. The extracted 6Z-C15-Wittig salts are, used in the synthesis of lycopenes with high 6Z contents and the residues are used in the synthesis of lycopenes with high All-E contents.
Plant carotene cis-trans isomerase CRTISO: A new member of the FAD red-dependent flavoproteins catalyzing non-redox reactions
Yu, Qiuju,Ghisla, Sandro,Hirschberg, Joseph,Mann, Varda,Beyer, Peter
experimental part, p. 8666 - 8676 (2012/03/08)
The carotene cis-trans isomerase CRTISO is a constituent of the carotene desaturation pathway as evolved in cyanobacteria and prevailing in plants, in which a tetra-cis-lycopene species, termed prolycopene, is formed. CRTISO, an evolutionary descendant of the bacterial carotene desaturase CRTI, catalyzes the cis-to-trans isomerization reactions leading to all-trans-lycopene, the substrate for the subsequent lycopene cyclization to form all-trans-α/ β-carotene. CRTISO and CRTI share a dinucleotide binding motif at the N terminus. Here we report that this site is occupied by FAD in CRTISO. The reduced form of this cofactor catalyzes a reaction not involving net redox changes. Results obtained with C(1)- and C(5)-deaza-FAD suggest mechanistic similarities with type II isopentenyl diphosphate: dimethylallyl diphosphate isomerase (IDI-2). CRTISO, together with lycopene cyclase CRTY and IDI-2, thus represents the third enzyme in isoprenoid metabolism belonging to the class of non-redox enzymes depending on reduced flavin for activity. The regional specificity and the kinetics of the isomerization reaction were investigated in vitro using purified enzyme and biphasic liposome-based systems carrying specific cis-configured lycopene species as substrates.Thereaction proceeded from cis to trans, recognizing half-sides of the symmetrical prolycopene and was accompanied by one trans-to-cis isomerization step specific for the C(5)-C(6) double bond. Rice lycopene β-cyclase (OsLCY-b), when additionally introduced into the biphasic in vitro system used, was found to be stereospecific for all-trans-lycopene and allowed the CRTISO reaction to proceed toward completion by modifying the thermodynamics of the overall reaction.
Synthesis, Isolation, and NMR-Spectroscopic Characterization of Fourteen (Z)-Isomers of Lycopene and of Some Acetylenic Didehydro- and Tetradehydrolycopenes
Hengartner, Urs,Bernhard, Kurt,Meyer, Karl,Englert, Gerhard,Glinz, Ernst
, p. 1848 - 1865 (2007/10/02)
Eight (Z)-isomers of lycopene were prepared by stereocontrolled syntheses and fully characterized by 1H-NMR, 13C-NMR, mass, and UV/VIS-spectroscopy: (5Z)-, (7Z)-, (15Z)-, (5Z,5'Z)-, (7Z,7'Z)-, (7Z,9Z)-, (9Z,9'Z)-, and (7Z,9Z,7'Z,9'Z)-lycopene.Six additional (Z)-isomers, namely (9Z)-, (13Z)-, (5Z,9'Z)-, (9Z,13'Z)-, (5Z,9Z,5'Z)-, and (5Z,13Z,5'Z)-lycopene, were isolated in small quantities from isomer mixtures by semiprep.HPLC and were identified by 1H-NMR spectroscopy.
