145633-21-2

Upstream product

• 2361-24-2 7,9,9',7'-tetra-cis-lycopene 
• 20082-23-9 (4E,6E/Z)-3,7,11-Trimethyldodeca-4,6,10-trien-1-yn-3-ol 
• 1071-89-2 (4E,6E/Z)-3,7,11-Trimethyldodeca-1,4,6,10-tetraen-3-ol 
• 58689-15-9 pseudoionone 
• 103793-14-2 [(2E,6E)-8-(Diethoxy-phosphoryl)-2,7-dimethyl-octa-2,6-dien-4-ynyl]-phosphonic acid diethyl ester 
• 5056-17-7 (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial 
• 145571-84-2 Triphenyl<(2E,4E,6Z)-3,7,11-trimethyldodeca-2,4,6,10-tetraenyl>phosphonium Bromide 

Downstream Products

• 4418-71-7 lycopene 
• 502-65-8 lycopene 

Relevant academic research and scientific papers

Plant carotene cis-trans isomerase CRTISO: A new member of the FAD red-dependent flavoproteins catalyzing non-redox reactions

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

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.

Synthesen von Carotinen mit ψ-Endgruppen und (Z)-Konfiguration an terminalen konjugierten Doppelbindungen

Five carotenes bearing (5Z)-ψ-end groups were synthesized and carefully characterized: (5Z)-lycopene (6), (5Z,5'Z)-lycopene (7), (5'Z)-neurosporene (8), (5'Z)-β,ψ-carotene (12), and (5'Z)-εψ-carotene (14).