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The biosynthesis of 24-isopropyl sterols comprising 99% of the sterols of the Great Barrier Reef sponge Pseudaxinyssa sp. was studied. The major biosynthetic pathway was established by incorporation of 24-methylenecholesterol-[28-14C], fucosterol-[22-T], isofucosterol-(22-T], (24R)-24-isopropenylcholesterol-(29-14C], (24S)-24-isopropenylcholesterol-[29-14C], DL-mevalonate-(2-14C] and L-methionine-[methyl-14C]. Very efficient side chain branching through double alkylation at C28 was demonstrated in contrast to relatively poor de novo biosynthesis. A stereoselective mode for hydrogen migration is observed and a regioselective mode is proposed for this migration.
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Stoilov et al. (1986) studied this question.
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