The enzymatic oxidation of alkanes to produce alcohols is a simplifi ed version of the
Chapter 4, Problem 50(choose chapter or problem)
The enzymatic oxidation of alkanes to produce alcohols is a simplifi ed version of the reactionsthat produce the adrenocortical steroid hormones. In the biosynthesis of corticosterone fromprogesterone (Section 4-7), two such oxidations take place successively (a, b). It is thoughtthat the monooxygenase enzymes act as complex oxygen-atom donors in these reactions.P r o b l e m sHHCO3CH3 CH3CH3{$Africanone(Also a plant-leaf oil)N NHN NHHO OHO OO OO OHOCH2CH3H CH H3CH2OH{BK B A suggested mechanism, as applied to cyclohexane, consists of the two steps shown belowthe biosynthesis.ProgesteroneSteroidmonooxygenases,O2?DP%%OCH3CH3H3CC Oab[Corticosterone%%CH3HOHOCH2O?CH3DPC OO (atom) OHOHEnzyme Calculate DH 8 for each step and for the overall oxidation reaction of cyclohexane. Use the followingDH 8 values: cyclohexane C H bond, 98.5 kcal mol21; bond in O H radical, 102.5 kcal mol21;cyclohexanol C O bond, 96 kcal mol21.K 0{0% %% % % %Thymidine dimer(A component of DNA that has beenexposed to ultraviolet light)CH3CH3H3C -Pinene(Present in cedar-wood oil)COOH1-Aminocyclopropanecarboxylicacid(Present in plants, this moleculeplays a role in the ripening of fruitsand the dropping of autumn leaves)
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