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Citations to this article

Biosynthesis of Chenodeoxycholic Acid in Man: STEREOSPECIFIC SIDE-CHAIN HYDROXYLATIONS OF 5β-CHOLESTANE-3α, 7α-DIOL
S. Shefer, … , G. S. Tint, G. Salen
S. Shefer, … , G. S. Tint, G. Salen
Published September 1, 1978
Citation Information: J Clin Invest. 1978;62(3):539-545. https://doi.org/10.1172/JCI109158.
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Biosynthesis of Chenodeoxycholic Acid in Man: STEREOSPECIFIC SIDE-CHAIN HYDROXYLATIONS OF 5β-CHOLESTANE-3α, 7α-DIOL

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Abstract

Stereospecific side-chain hydroxylations of 5β-cholestane-3α, 7α-diol were studied in mitochondrial and microsomal fractions of human liver. Incubation of 5β-cholestane-3α, 7α-diol resulted in hydroxylations at C-12, C-24, C-25, and C-26. Hydroxylations at C-24 and C-26 were accompanied by the introduction of additional asymmetric carbon atoms at C-24 and C-25 respectively, that led to the formation of two distinct pairs of diastereoisomers, namely 5β-cholestane-3α, 7α,24-triols (24R and 24S) and 5β-cholestane-3α, 7α,26-triols (25R and 25S). A sensitive and reproducible radioactive assay to measure the formation of the different biosynthetic 5β-cholestanetriols was developed. Optimal assay conditions for human mitochondrial and microsomal systems were tentatively established.

Authors

S. Shefer, F. W. Cheng, A. K. Batta, B. Dayal, G. S. Tint, G. Salen

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Total citations by year

Year: 2013 2005 2002 2001 2000 1997 1996 1990 1985 1984 1983 1982 1981 1980 1979 Total
Citations: 1 1 2 2 1 3 1 1 1 2 2 2 4 5 2 30
Citation information
This citation data is accumulated from CrossRef, which receives citation information from participating publishers, including this journal. Not all publishers participate in CrossRef, so this information is not comprehensive. Additionally, data may not reflect the most current citations to this article, and the data may differ from citation information available from other sources (for example, Google Scholar, Web of Science, and Scopus).

Citations to this article (30)

Title and authors Publication Year
α-Methylacyl-CoA racemase (AMACR): Metabolic enzyme, drug metabolizer and cancer marker P504S
MD Lloyd, M Yevglevskis, GL Lee, PJ Wood, MD Threadgill, TJ Woodman
Progress in Lipid Research 2013
Cytochrome P450
PR de Montellano
Cytochrome P450 2005
Gallstones
A Nakeeb, AG Comuzzie, L Martin, GE Sonnenberg, D Swartz-Basile, AH Kissebah, HA Pitt
Annals of Surgery 2002
Current Views of Fatty Acid Oxidation and Ketogenesis
PA Quant, S Eaton
2002
Fibroblast studies documenting a case of peroxisomal 2-methylacyl-CoA racemase deficiency: possible link between racemase deficiency and malabsorption and vitamin K deficiency
PP van Veldhoven, E Meyhi, RH Squires, M Fransen, B Fournier, V Brys, MJ Bennett, GP Mannaerts
European Journal of Clinical Investigation 2001
Plasma analysis of di- and trihydroxycholestanoic acid diastereoisomers in peroxisomal α-methylacyl-CoA racemase deficiency
S Ferdinandusse, H Overmars, S Denis, HR Waterham, RJ Wanders, P Vreken
Journal of lipid research 2001
Mitochondrial and peroxisomal targeting of 2-methylacyl-CoA racemase in humans
L Amery, M Fransen, KD Nys, GP Mannaerts, PP Veldhoven
Journal of lipid research 2000
2-Methylacyl racemase: a coupled assay based on the use of pristanoyl-CoA oxidase/peroxidase and reinvestigation of its subcellular distribution in rat and human liver
P Vanveldhoven, K Croes, M Casteels, G Mannaerts
Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism 1997
Stereochemistry of Peroxisomal and Mitochondrial beta-oxidation of alpha-methylacyl-CoAs
W Schmitz, E Conzelmann
European Journal of Biochemistry 1997
Comparative studies on ω-hydroxylation of 5β-cholestane-3α, 7α,12α-triol in the mitochondrial and microsomal fraction of the liver from several vertebrates
M Une, HG Kim, M Yoshii, T Kuramoto, T Hoshita
Steroids 1997
Peroxisomal β-oxidation of 2-methyl-branched acyl-CoA esters stereospecific recognition of the 2S-methyl compounds by trihydroxycoprostanoyl-CoA oxidase and pristanoyl-CoA oxidase
PP van Veldhoven, K Croes, S Asselberghs, P Herdewijn, GP Mannaerts
FEBS Letters 1996
26-Hydroxycholesterol: synthesis, metabolism, and biologic activities
NB Javitt
Journal of lipid research 1990
Biosynthesis of bile acids in cerebrotendinous xanthomatosis. Relationship of bile acid pool sizes and synthesis rates to hydroxylations at C-12, C-25, and C-26
G Salen, S Shefer, GS Tint, G Nicolau, B Dayal, AK Batta
Journal of Clinical Investigation 1985
Formation and Metabolism of Bile Alcohols in Man
G Karlaganis, J SjÖVall
Hepatology 1984
Bile Alcohols in Perspective
NB Javitt
Hepatology 1984
Regulation of bile acid synthesis in man. Presence of a diurnal rhythm
WC Duane, DG Levitt, SM Mueller, JC Behrens
Journal of Clinical Investigation 1983
Configuration at C-25 in 3 alpha, 7 alpha, 12 alpha-trihydroxy-5 beta-cholestan-26-oic acid isolated from human bile
AK Batta, G Salen, S Shefer, B Dayal, GS Tint
Journal of lipid research 1983
Bile Acid Metabolism in Cirrhosis. VIII. Quantitative Evaluation of Bile Acid Synthesis From [7β-3H]7α-Hydroxycholesterol and [G-3H]26-Hydroxycholesterol
M Goldman, ZR Vlahcevic, CC Schwartz, J Gustafsson, L Swell
Hepatology 1982
Metabolism of iso-bile acids in the rat
S Shefer, G Salen, S Hauser, B Dayal, AK Batta
The Journal of biological chemistry 1982
The Biology of Cholesterol and Related Steroids
NB Myant
The Biology of Cholesterol and Related Steroids 1981
Biosynthesis of bile acids in man. An in vivo evaluation of the conversion of R and S 3 alpha, 7 alpha, 12 alpha-trihydroxy-5 beta-cholestanoic and 3 alpha, 7 alpha, 12 alpha-24 xi-tetrahydroxy-5 beta-cholestanoic acids to cholic acid
L Swell, J Gustafsson, H Danielsson, CC Schwartz, ZR Vlahcevic
The Journal of biological chemistry 1981
Cerebrotendinous xanthomatosis: defective liver mitochondrial hydroxylation of chenodeoxycholic acid precursors
H Oftebro, I Björkhem, FC Størmer, JI Pedersen
Journal of lipid research 1981
On the stereospecificity of cholestanetriol 26-monooxygenase
Y Atsuta, K Okuda
The Journal of biological chemistry 1981
Cerebrotendinous xanthomatosis: a defect in mitochondrial 26-hydroxylation required for normal biosynthesis of cholic acid
H Oftebro, I Björkhem, S Skrede, A Schreiner, JI Pederson
Journal of Clinical Investigation 1980
Disturbances in bile acid metabolism of infants with the Zellweger (cerebro-hepato-renal) syndrome
L Monnens, J Bakkeren, G Parmentier, G Janssen, U van Haelst, F Trijbels, H Eyssen
European Journal of Pediatrics 1980
An in vivo evaluation of the quantitative significance of several potential pathways to cholic and chenodeoxycholic acids from cholesterol in man
L Swell, J Gustafsson, CC Schwartz, LG Halloran, H Danielsson, ZR Vlahcevic
Journal of lipid research 1980
Stereochemistry of the side chain oxidation of 5 beta-cholestane-3 alpha,7 alpha,12 alpha-triol in man
RF Hanson, PS Leeuwen, GC Williams
The Journal of biological chemistry 1980
Differentiation between the 25R- and 25S-isomers of 5 beta-cholestane-3 alpha, 7 alpha, 26-triol by 13C NMR spectroscopy
AK Batta, TH Williams, G Salen, DN Greeley, S Shefer
Journal of lipid research 1980
Configuration at C-25 in 3 alpha, 7 alpha, 12 alpha-trihydroxy-5 beta-cholestan-26-oic acid by X-ray crystallography
AK Batta, G Salen, JF Blount, S Shefer
Journal of lipid research 1979
26-Hydroxylation of C27-steroids by soluble liver mitochondrial cytochrome P-450
JI Pedersen, I Björkhem, J Gustafsson
The Journal of biological chemistry 1979

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