KEGG ENZYME: 1.14.14.57

ENZYME: 1.14.14.57

Entry

EC 1.14.14.57               Enzyme

Name

taurochenodeoxycholate 6alpha-hydroxylase;
CYP3A4;
CYP4A21;
taurochenodeoxycholate 6alpha-monooxygenase

Class

Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor

Sysname

taurochenodeoxycholate,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (6alpha-hydroxylating)

Reaction(IUBMB)

(1) taurochenodeoxycholate + [reduced NADPH---hemoprotein reductase] + O2 = taurohyocholate + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R07205];
(2) lithocholate + [reduced NADPH---hemoprotein reductase] + O2 = hyodeoxycholate + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R07206]

Reaction(KEGG)

R07205 R07206

Substrate

taurochenodeoxycholate [CPD:C05465];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007];
lithocholate [CPD:C03990]

Product

taurohyocholate [CPD:C15516];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
H2O [CPD:C00001];
hyodeoxycholate [CPD:C15517]

Comment

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].

History

EC 1.14.14.57 created 2005 asEC 1.14.13.97, transferred 2018 to EC 1.14.14.57

Orthology

K17689

cytochrome P450 family 3 subfamily A4

K18228

taurochenodeoxycholate 6alpha-hydroxylase

Genes

HSA:	1576(CYP3A4)

PTR:	463582(CYP3A4)

PPS:	100976899(CYP3A4)

GGO:

101149513

PON:

100436782

PPYG:

129041698

NLE:

100593175

SSYN:

129489604

MCC:	678670(CYP3A4)

MCF:	102144258(CYP3A4)

MTHB:

126950475

MNI:

105497389

CSAB:

103246766

CATY:

105584402

PANU:

101026757

TGE:

112621193

MLEU:

105543708

RRO:

104673585

RBB:

108538168

TFN:

117072034

PTEH:

111530171 111534893

CANG:

105513064

CJC:	100404344(CYP3A4)

SBQ:

101037403

CIMI:

108308036(CYP3A4)

ANAN:

105719456(CYP3A4)

CSYR:

103252931

MMUR:

105868328 105868331

LCAT:

123631591 123631593

PCOQ:

105806078

OGA:

100948865

SSC:	403327(CYP4A21)

» show all

Reference

1 [PMID:10216279]

Authors

Araya Z, Wikvall K.

Title

6alpha-hydroxylation of taurochenodeoxycholic acid and lithocholic acid by CYP3A4 in human liver microsomes.

Journal

Biochim Biophys Acta 1438:47-54 (1999)
DOI:10.1016/S1388-1981(99)00031-1

Sequence

[hsa:1576]

Reference

2 [PMID:7649186]

Authors

Araya Z, Hellman U, Hansson R.

Title

Characterisation of taurochenodeoxycholic acid 6 alpha-hydroxylase from pig liver microsomes.

Journal

Eur J Biochem 231:855-61 (1995)
DOI:10.1111/j.1432-1033.1995.0855d.x

Sequence

[ssc:403327]

Reference

3 [PMID:11069906]

Authors

Kramer W, Sauber K, Baringhaus KH, Kurz M, Stengelin S, Lange G, Corsiero D, Girbig F, Konig W, Weyland C.

Title

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.

Journal

J Biol Chem 276:7291-301 (2001)
DOI:10.1074/jbc.M006877200

Reference

4 [PMID:11113117]

Authors

Lundell K, Hansson R, Wikvall K

Title

Cloning and expression of a pig liver taurochenodeoxycholic acid 6alpha-hydroxylase (CYP4A21): a novel member of the CYP4A subfamily.

Journal

J Biol Chem 276:9606-12 (2001)
DOI:10.1074/jbc.M006584200

Sequence

[ssc:403327]

Reference

5 [PMID:14643796]

Authors

Lundell K, Wikvall K.

Title

Gene structure of pig sterol 12alpha-hydroxylase (CYP8B1) and expression in fetal liver: comparison with expression of taurochenodeoxycholic acid 6alpha-hydroxylase (CYP4A21).

Journal

Biochim Biophys Acta 1634:86-96 (2003)
DOI:10.1016/j.bbalip.2003.09.002

Reference

6 [PMID:12543708]

Authors

Russell DW

Title

The enzymes, regulation, and genetics of bile acid synthesis.

Journal

Annu Rev Biochem 72:137-74 (2003)
DOI:10.1146/annurev.biochem.72.121801.161712

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