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20α,22R-Dihydroxycholesterol


20α,22R-Dihydroxycholesterol, or 3β-cholest-5-ene-3,20,22-triol is an endogenous, metabolic intermediate in the biosynthesis of the steroid hormones from cholesterol Cholesterol 3β-cholest-5-en-3-ol is hydroxylated by cholesterol side-chain cleavage enzyme P450scc to form 22R-hydroxycholesterol, which is subsequently hydroxlated again by P450scc to form 20α,22R-dihydroxycholesterol, and finally the bond between carbons 20 and 22 is cleaved by P450scc to form pregnenolone 3β-3-hydroxypregn-5-en-20-one, the precursor to the steroid hormones

See also

  • 22R-Hydroxycholesterol
  • 27-Hydroxycholesterol

References

  1. ^ a b CHAUDHURI AC, HARADA Y, SHIMIZU K, GUT M, DORFMAN RI March 1962 "Biosynthesis of pregnenolone from 22-hydroxycholesterol" The Journal of Biological Chemistry 237: 703–4 PMID 13878470 
  2. ^ a b Hume R, Kelly RW, Taylor PL, Boyd GS May 1984 "The catalytic cycle of cytochrome P-450scc and intermediates in the conversion of cholesterol to pregnenolone" European Journal of Biochemistry / FEBS 140 3: 583–91 doi:101111/j1432-10331984tb08142x PMID 6723652 




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