Steric considerations regarding the biodegradation of cholesterol to pregnenolone.-exclusion of (22S)-22-hydroxycholesterol and 22-ketocholesterol as intermediates

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Abstract

(22S)-[22-3H1]-Cholesterol was incubated with an adrenocortical preparation and the isolated (22R)-[22-3H1]-22-hydroxycholesterol had a small loss of radioactivity, proving that direct replacement of the hydrogen from the now hydroxylated position occurred.

In addition [1-3H1]-4-methylpentanol was isolated, which also had incurred a relatively small loss of its specific activity, thereby excluding (20R)-3β,20-dihydroxycholest-5-en-22-one as an important metabolite in the degradation of cholesterol to pregnenolone by adrenal tissue.

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