Stereochemistry of allene biosynthesis and the formation of the acetylenic carotenoid diadinoxanthin and peridinin (C37) from neoxanthin.
Intact cells of the alga Amphidinium carterae (Dinophyceae), and a cell-free system prepared from it, incorporated 14C, 3H-labelled mevalonate into lycopene, beta, beta-carotene, zeaxanthin, neoxanthin, diadinoxanthin and peridinin. The 14C/3H ratios of zeaxanthin, neoxanthin and diadinoxanthin formed from (2RS,3R)-[2-14C,2-3H2]mevalonate show that a hydrogen atom from C-2 of mevalonate is retained in the allene at C-8, and also at C-12 of peridinin. (3R,4R + 3S,4S)-[2-14C,4-3H1]Mevalonate gave 14C/3H ratios in peridinin which show that C-14 is lost. The three carbon atoms excised during the formation of the C37 carotenoid peridinin are C-13, C-14 and C-20 of neoxanthin.
D000114:Acetylene / Q000096:biosynthesis; D002338:Carotenoids / Q000096:biosynthesis* / Q000378:metabolism*; D002474:Cell-Free System; D055598:Chemical Phenomena; D002621:Chemistry; D056890:Eukaryota / Q000378:metabolism*; D008798:Mevalonic Acid / Q000378:metabolism; D008968:Molecular Conformation; D024341:Xanthophylls
D024341:Xanthophylls; C033808:diadinoxanthin; C016040:peridinin; D002338:Carotenoids; C011947:neoxanthin; D000114:Acetylene; D008798:Mevalonic Acid