20alpha,22x-Dihydroxycholesterol, an intermediate in the biosynthesis of pregnenolone (3beta-hydroxypregn-5-en-20-one) from cholesterol.

No abstract is available for this paper.

• Publication year

  1962

• Venue

  Journal of Biological Chemistry

• Publication date

  1962-03-01

• Fields of study

  Biology, Medicine, Chemistry

• Identifiers
  PMID 13911962
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

• Cleavage of cholesterol side chain by adrenal cortex. I. Cofactor requirement and product of clevage.

  1961cited by this paper
• Reversed phase paper chromatography and detection of steroids of the cholesterol class.

  1957cited by this paper
• Paper partition chromatography of C19-and C21-ketosteroids.

  1953cited by this paper

• Functional zonation of the rat adrenal cortex: the development and maintenance

  2014cites this paper
• Cytotoxic steroidal alkaloids from Kibatalia laurifolia.

  2011cites this paper
• Reaction of steroidal alcohols with isobutene. Usefulness of t-butyl as a hydroxyl-protecting group in a synthesis of testosterone

  2010cites this paper
• Cyanosilylation at pregnane side-chains. Selective synthesis and crystal structure of 20(R)-silylated cyanohydrins.

  2005cites this paper
• Stereoselective reactions of (20R)-3,20-dihydroxy-(3',4'-dihydro-2'H-pyranyl)-5-pregnene derivatives form 27-nor-3,20,23,26-tetrahydroxy-cholesten-22-ones and related bromo ketones.

  2004cites this paper
• Overview of dehydroepiandrosterone biosynthesis.

  2004cites this paper
• Funktionsmorphologie des Interrenalorgans von Rana temporaria L.

  2004cites this paper
• Overview of Dehydroepiandrosterone Biosynthesis

  2004cites this paper
• A pathway for the metabolism of vitamin D3: Unique hydroxylated metabolites formed during catalysis with cytochrome P450scc (CYP11A1)

  2003cites this paper
• Identification of the Lipophilic Factor Produced by Macrophages That Stimulates Steroidogenesis.

  2000cites this paper
• Role of Neutral Metabolites in Microbial Conversion of 3β-Acetoxy-19-Hydroxycholest-5-Ene into Estrone

  1994cites this paper
• Heterogeneity of adult mouse Leydig cells with different buoyant densities.

  1992cites this paper
• Purification and comparative characterization of cytochrome P-450scc from porcine adrenocortical mitochondria.

  1991cites this paper
• Purification and comparative characterization of cytochrome P-450scc from porcine adrenocortical mitochondria.

  1991cites this paper
• Cytochrome P-450scc-catalyzed production of progesterone from 22R-hydroxycholest-4-en-3-one by way of 20,22-dihydroxycholest-4-en-3-one.

  1990cites this paper
• Reconsidering Some of the Biosynthetic Pathways Leading to Formation of C19‐Steroids

  1990cites this paper
• Heterodox notions on pathways of steroidogenesis.

  1990cites this paper
• Comparison of components of the testis interstitium with testosterone secretion in hamster, rat, and guinea pig testes perfused in vitro.

  1988cites this paper
• Familial lipoid adrenal hyperplasia: genetic marker data and an approach to prenatal diagnosis.

  1986cites this paper
• The catalytic cycle of cytochrome P-450scc and intermediates in the conversion of cholesterol to pregnenolone.

  1984cites this paper
• Mechanism of hydroxylation at C-22 during the biosynthesis of ecdysteroids in the locust Schistocerca gregaria.

  1982cites this paper
• Ascorbic acid inhibition of aromatase activity in human placenta tissue.

  1981cites this paper
• THERMODYNAMIC AND KINETIC PROPERTIES OF THE ADRENOCORTICAL MITOCHONDRIAL CYTOCHROME P450 WHICH CONVERTS CHOLESTEROL INTO PREGNENOLONE

  1980cites this paper
• Biosynthesis and transformation of 20α 21-dihydroxycholesterol by rat adrenal preparations

  1979cites this paper
• Biosynthesis and transformation of 20 alpha, 21-dihydroxycholesterol by rat adrenal preparations.

  1979cites this paper
• Inborn errors of steroid biosynthesis.

  1979cites this paper
• Effect of ascorbic acid on in vitro rat adrenal & ovarian steroidogenesis.

  1979cites this paper
• Hormone secretion in the corpus luteum

  1979cites this paper
• Cytochrome P450 in adrenocortical mitochondria

  1979cites this paper
• Steroid binding properties of beef adrenal cortical cytochrome P-450 which catalyzes the conversion of cholesterol into pregnenolone.

  1979cites this paper
• The recently proposed 20,22-epoxycholesterol as the intermediate in the conversion of cholesterol to pregnenolone by adrenal cortex mitochondria must be 5α,6α-epoxycholestan-3β-ol

  1978cites this paper
• Biosynthesis of pregnenolone from cholesterol by mitochondrial enzymes of bovine adrenal cortex. The question of the participation of the 20(22)-olefins and 20, 22-epoxides of cholesterol.

  1978cites this paper
• The recently proposed 20,22-epoxycholesterol as the intermediate in the conversion of cholesterol to pregnenolone by adrenal cortex mitochondria must be 5alpha,6alpha-epoxycholestan-3beta-ol.

  1978cites this paper
• Effects of adrenal steroid activator protein on the conversion of various 20- and 22-hydroxycholesterols to pregnenolone by adrenal mitochondrial enzymes.

  1978cites this paper
• Specificity of the cholesterol side-chain cleavage enzyme system of adrenal cortex.

  1977cites this paper
• [Molecular mechanism of enzymic cleavage of cholesterol side chain (author's transl)].

  1977cites this paper
• Inhibition of cholesterol side-chain cleavage by 22-azacholesterol.

  1977cites this paper
• Purification and characterization of adrenal cortex mitochondrial cytochrome P-450 specific for cholesterol side chain cleavage activity.

  1976cites this paper
• Inhibition of the conversion of cholesterol to pregnenolone in bovine adrenocortical preparations.

  1976cites this paper
• Molecular aspects of the biosynthesis of adrenal steroids.

  1976cites this paper
• Stereochemically controlled syntheses of 20,22-epoxycholesterols

  1976cites this paper
• Stereospecific synthesis of the four 20,22-epoxycholesterols and of (Z)-20(22)-dehydrocholesterol.

  1976cites this paper
• Intermediates in the conversion of cholesterol to pregnenolone: kinetics and mechanism.

  1976cites this paper
• Immunochemical studies on adrenal ferredoxin: involvement of adrenal ferredoxin in the cholesterol side-chain cleavage reaction of mammalian adrenals.

  1976cites this paper
• Biological action of gonadotropins in the male.

  1976cites this paper
• Oxygenase-catalyzed biological hydroxylations.

  1975cites this paper
• Incorporation of H2 18O into 20α, 22R‐di‐OH cholesterol: Evidence for an epoxide—diol pathway in the adrenocortical cholesterol side‐chain cleavage mechanism

  1975cites this paper
• Mechanism of Action of Androgens

  1975cites this paper
• The active form of cytochrome P-450 from bovine adrenocortical mitochondria.

  1975cites this paper
• Enzymic studies on adrenocortical deoxycorticosterone 11beta-hydroxylase system.

  1975cites this paper
• The role of mitochondrial cytochrome P-450 from bovine adrenal cortex in side chain cleavage of 20S,22R-dihydroxycholesterol.

  1975cites this paper
• Zur biogenese des tigogenins in Digitalis lanata und des solasodins in Solanum laciniatum

  1975cites this paper
• 2 – OXYGENASES IN FATTY ACID AND STEROID METABOLISM

  1974cites this paper
• Adrenocorticotrophic hormone and the control of adrenal corticosteroidogenesis.

  1974cites this paper
• THE ROLE OF CYTOCHROME P. 450 IN THE SIDE-CHAIN CLEAVAGE OF CHOLESTEROL

  1974cites this paper
• The stoichiometry of the conversion of cholesterol and hydroxycholesterols to pregnenolone (3beta-hydroxypregn-5-en-20-one) catalysed by adrenal cytochrome P-450.

  1974cites this paper
• Metabolic regulation of steroid steroidogenesis in isolated adrenal and adrenocortical carcinoma cells of rat. The incorporation of (20S)-20-(7- 3 H)hydroxycholesterol into deoxycorticosterone and corticosterone.

  1973cites this paper
• Cytochrome P-450 from bovine adrenocortical mitochondria: an enzyme for the side chain cleavage of cholesterol. I. Purification and properties.

  1973cites this paper
• Chemie der Androgene

  1973cites this paper
• Oxidation of 20 -hydroxycholesterol by adrenal cortex mitochondria.

  1973cites this paper
• KINETIC STUDIES ON THE MECHANISM OF CONVERSION OF CHOLESTEROL TO PREGNENOLONE *

  1973cites this paper
• PROPERTIES OF SOLUBLE CYTOCHROMES P‐450 FROM BOVINE ADRENOCORTICAL MITOCHONDRIA

  1973cites this paper
• [Enzyme histochemical studies on metabolism of steroids and steroid conjugates in the juxtamedullary X-zone of the mouse].

  1973cites this paper
• The effect of ether anaesthesia stress on cholesterol-side-chain cleavage and cytochrome P450 in rat-adrenal mitochondria.

  1972cites this paper
• Studies on the biosynthetic conversion of cholesterol into pregnenolone. Side chain cleavage of a t-butyl analog of 20 -hydroxycholesterol, (20R(-t-butyl-5-pregnene-3 ,20-diol, a compound completely substituted at C-22.

  1972cites this paper
• Evidence for deficient 20 -cholesterol-hydroxylase activity in adrenal tissue of a patient with lipoid adrenal hyperplasia.

  1972cites this paper
• Effects of oxygenated cholesterol derivatives on adrenal cortex mitochondria.

  1972cites this paper
• Studies on P-450. IX. Properties of a P-450 preparation showing high spin type absorption spectrum obtained from adrenal cortex mitochondria.

  1972cites this paper
• A possible role for transhydrogenation in side-chain cleavage of cholesterol.

  1972cites this paper
• Stereospecific synthesis of (20S,22R)-17 ,20,22-trihydroxycholesterol and (20S,22S)-17 ,20,22-trihydroxycholesterol.

  1972cites this paper
• Biosynthesis of pregnane derivatives.

  1971cites this paper
• 5 Antifertility Agents

  1971cites this paper
• Role of Reduced TPN in the Response to Interstitial Cell Stimulating Hormone

  1971cites this paper
• Abnormal progesterone synthesis in placental tissue from a spontaneous abortion.

  1971cites this paper
• Inhibition of cholesterol side-chain cleavage by azacholesterols.

  1971cites this paper
• Biosynthesis of pregnenolone.

  1971cites this paper
• Sterol metabolism. 8. Conversion of cholesterol 20 alpha-hydroperoxide to 20 alpha, 21- and 20 alpha, 22R-dihydroxycholesterol by adrenal cortex mitochondria.

  1970cites this paper
• Substrate-induced changes in visible absorption and electron spin resonance properties of adrenal cortex mitochondrial P450.

  1970cites this paper
• Sterol metabolism. 13. Chromatographic resolution of the epimeric 24-hydroxycholesterols.

  1970cites this paper
• Effects of ascorbic acid on the side-chain cleavage of cholesterol.

  1970cites this paper
• Studies on P-450. VII. Reconstitution of a steroid 11-beta-hydroxulation system using a P-450 preparation extracted and partially purified from adenocortical mitochondria.

  1970cites this paper
• Effects of ascorbic acid on the side-chain cleavage of cholesterol.

  1970cites this paper
• The synthesis and stereochemistry of (22R)-20 alpha, 22- and (22S)-20 alpha, 22-dihydroxycholesterol.

  1970cites this paper
• The synthesis and stereochemistry of (22R)-20α,22- and (22S)-20α,22-dihydroxycholesterol

  1970cites this paper
• Sterol metabolism. XVI. Cholesterol 20-alpha-hydroperoxide as an intermediate in pregnenolone biosynthesis from cholesterol.

  1970cites this paper
• Sterol metabolism VIII. Conversion of cholesterol 20α-hydroperoxide to 20α, 21- and 20α,22R-dihydroxycholesterol by adrenal cortex mitochondria

  1970cites this paper
• Studies on adrenal cortical cytochrome P-450. IV. Effects of carbon monoxide and light on cholesterol side chain cleavage.

  1970cites this paper
• CHAPTER 1 – Endocrinology of the Testis

  1970cites this paper
• [Histochemical behavior of alcohol dehydrogenases as well as various oxidoreductases in the rat testis after testosterone administration].

  1969cites this paper
• [A contribution to the ultrastructural study of the interrenal cells of Salamandra salamandra L. (urodele amphibian). I. Normal conditions].

  1969cites this paper
• Reactions of 20-hydroxylated steroids with bovine adrenal tissue preparations.

  1969cites this paper
• The cholesterol side-chain cleavage enzymes in steroid hormone-producing tissues.

  1969cites this paper
• 6 – THE BIOCHEMISTRY OF GONADAL HORMONES AND RELATED COMPOUNDS

  1969cites this paper
• Contribution à l'étude ultrastructurale des cellules interrénales de Salamandra salamandra L. (Amphibien Urodèle)

  1969cites this paper
• The side-chain cleavage of cholesterol and cholesterol sulfate by enzymes from bovine adrenocortical mitochondria.

  1969cites this paper
• A preliminary report on the intermediates in the conversion in vitro of cholesterol to pregnenolone in adrenal preparations.

  1969cites this paper
• [27] The cholesterol side-chain cleavage enzyme system of gonadal tissue

  1969cites this paper
• The occurrence and metabolism of 20 alpha-hydroxycholesterol in bovine adrenal preparations.

  1969cites this paper
• 3′,5′-Cyclic AMP and the Adrenal Desmolase System∗

  1969cites this paper
• Inhibition by cholesterol analogues of the side-chain cleavage of cholesterol and 20alpha-hydroxycholesterol in a preparation of hog adrenocortical mitochondria.

  1969cites this paper