肾上腺细胞色素P-450催化胆固醇和羟基胆固醇转化为孕烯醇酮（3β-羟基孕-5-烯-20-酮）的化学计量关系。
The stoichiometry of the conversion of cholesterol and hydroxycholesterols to pregnenolone (3beta-hydroxypregn-5-en-20-one) catalysed by adrenal cytochrome P-450.
作者信息
Shikita M, Hall P F
出版信息
Proc Natl Acad Sci U S A. 1974 Apr;71(4):1441-5. doi: 10.1073/pnas.71.4.1441.
Abstract
The stoichiometry of the side-chain cleavage of cholesterol (cholest-5-en-3beta-ol), 20alpha-hydroxycholesterol (cholest-5-ene-3beta,20alpha-diol), and 20alpha,22-dihydroxycholesterol (cholest-5-ene-3beta,20alpha,22-triol) has been examined with respect to TPNH, oxygen and H(+). Side-chain cleavage of cholesterol can be described by the following equation:Cholesterol + 3TPNH + 3H(+) + 3O(2) --> Pregnenolone (3beta-hydroxypregn-5-ene-20-one) + isocapraldehyde + 3 TPN(+) 4H(2)OStoichiometry of 20 alpha-hydroxycholesterol is 2TPNH and 2O(2) per mole of cleavage and with 20alpha, 22-dihydroxycholesterol the values are 1:1:1. In addition 1 mole of H(+) is consumed per mole of TPNH oxidized in each of these reactions. These observations are in keeping with a mechanism previously proposed in the literature, namely:Cholesterol --> 20alpha-OH-Cholesterol --> 20alpha, 22-di-OH-Cholesterol --> pregnenoloneDiscordant observations are reviewed and it is concluded that insufficient data are available to sustain objections to this pathway.
摘要
已针对还原型辅酶I（TPNH）、氧气和氢离子，研究了胆固醇（胆甾-5-烯-3β-醇）、20α-羟基胆固醇（胆甾-5-烯-3β,20α-二醇）和20α,22-二羟基胆固醇（胆甾-5-烯-3β,20α,22-三醇）侧链裂解的化学计量关系。胆固醇的侧链裂解可用以下方程式描述：
胆固醇 + 3TPNH + 3H⁺ + 3O₂ → 孕烯醇酮（3β-羟基孕-5-烯-20-酮）+ 异己醛 + 3TPN⁺ + 4H₂O
20α-羟基胆固醇的化学计量关系是每摩尔裂解消耗2TPNH和2O₂，而对于20α,22-二羟基胆固醇，其值为1:1:1。此外，在这些反应中，每氧化1摩尔TPNH会消耗1摩尔H⁺。这些观察结果与文献中先前提出的一种机制相符，即：
胆固醇 → 20α-羟基胆固醇 → 20α,22-二羟基胆固醇 → 孕烯醇酮
对不一致的观察结果进行了综述，得出的结论是，现有数据不足以支持对该途径的反对意见。
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The stoichiometry of the conversion of cholesterol and hydroxycholesterols to pregnenolone (3beta-hydroxypregn-5-en-20-one) catalysed by adrenal cytochrome P-450.肾上腺细胞色素P-450催化胆固醇和羟基胆固醇转化为孕烯醇酮（3β-羟基孕-5-烯-20-酮）的化学计量关系。
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