Stereochemistry of phytoene biosynthesis by isolated chloroplasts

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Abstract
The incorporation of [2−14C,(5R)-5−3H1]MVA* and [2−14C,5−3H2]MVA into geranylgeraniol and phytoene by a preparation of ‘non-aqueous’ bean leaf chloroplasts has been studied. In the formation of phytoene from two molecules of geranylgeranyl pyrophosphate, the loss of hydrogen is stereospecific, the hydrogen atom lost from C-1 of each molecule of geranylgeranyl pyrophosphate being that which was originally the pro-S hydrogen atom from C-5 of mevalonate. All the pro-R hydrogen atoms from C-5 of mevalonate are retained. These results with a cell-free system confirm and extend the observations made in previous work with tomato slices.