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Information on EC 1.14.14.57 - taurochenodeoxycholate 6alpha-hydroxylase for references in articles please use BRENDA:EC1.14.14.57
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EC Tree
IUBMB Comments A cytochrome P-450 (heme-thiolate) protein. Requires cytochrome b5 for maximal activity. Acts on taurochenodeoxycholate, taurodeoxycholate and less readily on lithocholate and chenodeoxycholate. In adult pig (Sus scrofa), hyocholic acid replaces cholic acid as a primary bile acid .
The enzyme appears in viruses and cellular organisms
Synonyms
CYP3A4, CYP4A21, taurochenodeoxycholate 6alpha-monooxygenase, taurochenodeoxycholic acid 6alpha-hydroxylase,
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taurochenodeoxycholate 6alpha-monooxygenase
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taurochenodeoxycholic acid 6alpha-hydroxylase
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CYP3A4
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CYP4A21
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lithocholate + [reduced NADPH-hemoprotein reductase] + O2 = hyodeoxycholate + [oxidized NADPH-hemoprotein reductase] + H2O
(2)
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taurochenodeoxycholate + [reduced NADPH-hemoprotein reductase] + O2 = taurohyocholate + [oxidized NADPH-hemoprotein reductase] + H2O
(1)
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taurochenodeoxycholate,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (6alpha-hydroxylating)
A cytochrome P-450 (heme-thiolate) protein. Requires cytochrome b5 for maximal activity. Acts on taurochenodeoxycholate, taurodeoxycholate and less readily on lithocholate and chenodeoxycholate. In adult pig (Sus scrofa), hyocholic acid replaces cholic acid as a primary bile acid [5].
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chenodeoxycholate + [reduced NADPH-hemoprotein reductase] + O2
hyocholate + [oxidized NADPH-hemoprotein reductase] + H2O
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lithocholate + [reduced NADPH-hemoprotein reductase] + O2
hyocholate + [oxidized NADPH-hemoprotein reductase] + H2O
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activity is low compared to activity with taurochenodeoxycholate
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lithocholate + [reduced NADPH-hemoprotein reductase] + O2
hyodeoxycholate + [oxidized NADPH-hemoprotein reductase] + H2O
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taurochenodeoxycholate + [reduced NADPH-hemoprotein reductase] + O2
taurohyocholate + [oxidized NADPH-hemoprotein reductase] + H2O
additional information
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isofornm CYP3A4 is the only enzyme tested which is active towards bile acids taurochenodeoxycholate and lithocholate. The enzyme catalyzes an efficient 6alpha-hydroxylation of both taurochenodeoxycholic acid and lithocholic acid
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taurochenodeoxycholate + [reduced NADPH-hemoprotein reductase] + O2
taurohyocholate + [oxidized NADPH-hemoprotein reductase] + H2O
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taurochenodeoxycholate + [reduced NADPH-hemoprotein reductase] + O2
taurohyocholate + [oxidized NADPH-hemoprotein reductase] + H2O
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troleandomycin
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0.01 mM, almost complete inhibition
additional information
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not inhibitory or very little effect: alpha-naphthoflavone, sulfaphenazole and tranylcypromine
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0.0629 - 0.09
taurochenodeoxycholate
0.0629
taurochenodeoxycholate
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0.09
taurochenodeoxycholate
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pH 7.4, 37°C
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SwissProt
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additional information
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expression is found in 4-day-old and 6-week-old pig liver, but not in fetal liver
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physiological function
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a strong correlation exists between 6alpha-hydroxylation of taurochenodeoxycholic acid, CYP3A levels and testosterone 6beta-hydroxylation. There is also a strong correlation between 6alpha-hydroxylation of lithocholic acid, CYP3A levels and testosterone 6beta-hydroxylation
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CP4AL_PIG
504
2
57216
Swiss-Prot
M5C979_THACB
Thanatephorus cucumeris (strain AG1-IB / isolate 7/3/14)
255
0
28921
TrEMBL
E0VSD4_PEDHC
Pediculus humanus subsp. corporis
529
0
61663
TrEMBL
A0A5A4CZ14_LOCMI
524
2
59287
TrEMBL
A0A0N0MNE2_9ACTN
1071
0
118335
TrEMBL
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53000
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x * 53000, SDS-PAGE
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6alpha-hydroxylase (CYP4A21) gene: evolution by gene duplication and gene conversion
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expression in insect cells
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transfection into COS cells
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medicine
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vitamin D receptor deficiency in the intestine of mice exacerbates lithocholic acid-induced hepatotoxicity manifested by increased necrosis and inflammation, due in part to overaccumulation of hepatic bile acids including taurocholic acid and taurodeoxycholic acid. Intestinal expression of CYP3A4 in the Vitamin D receptor-deficient mouse line reduces lithocholic acid-induced hepatotoxicity through elevation of lithocholic acid metabolism and detoxification, and suppression of bile acid transporter expression in the small intestine
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Russell, D.W.
The enzymes, regulation, and genetics of bile acid synthesis
Annu. Rev. Biochem.
72
137-174
2003
Homo sapiens
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Lundell, K.
The porcine taurochenodeoxycholic acid 6alpha-hydroxylase (CYP4A21) gene: evolution by gene duplication and gene conversion
Biochem. J.
378
1053-1058
2004
Sus scrofa (Q9GJX5), Sus scrofa
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Araya, Z.; Hellman, U.; Hansson, R.
Characterisation of taurochenodeoxycholic acid 6alpha-hydroxylase from pig liver microsomes
Eur. J. Biochem.
231
855-861
1995
Sus scrofa
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Kramer, W.; Sauber, K.; Baringhaus, K.H.; Kurz, M.; Stengelin, S.; Lange, G.; Corsiero, D.; Girbig F.; König, W.; Weyland, C.
Identification of the bile acid-binding site of the ileal lipid-binding protein by photoaffinity labeling, matrix-assisted laser desorption ionization-mass spectrometry, and NMR structure
J. Biol. Chem.
276
7291-7301
2001
Oryctolagus cuniculus
brenda
Lundell, K.; Hansson, R.; Wikvall, K.
Cloning and expression of a pig liver taurochenodeoxycholic acid 6alpha-hydroxylase (CYP4A21): a novel member of the CYP4A subfamily
J. Biol. Chem.
276
9606-9612
2001
Sus scrofa (Q9GJX5), Sus scrofa
brenda
Araya, Z.; Wikvall, K.
6alpha-hydroxylation of taurochenodeoxycholic acid and lithocholic acid by CYP3A4 in human liver microsomes
Biochim. Biophys. Acta
1438
47-54
1999
Homo sapiens
brenda
Lundell, K.; Wikvall, K.
Gene structure of pig sterol 12alpha-hydroxylase (CYP8B1) and expression in fetal liver comparison with expression of taurochenodeoxycholic acid 6alpha-hydroxylase (CYP4A21)
Biochim. Biophys. Acta
1634
86-96
2003
Sus scrofa (Q9GJX5), Sus scrofa
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Cheng, J.; Fang, Z.Z.; Kim, J.H.; Krausz, K.W.; Tanaka, N.; Chiang, J.Y.; Gonzalez, F.J.
Intestinal CYP3A4 protects against lithocholic acid-induced hepatotoxicity in intestine-specific VDR-deficient mice
J. Lipid Res.
55
455-465
2014
Mus musculus
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1.14.14.57 taurochenodeoxycholate 6alpha-hydroxylase
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