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:

GGO:

PON:

NLE:

MCC:	678670(CYP3A4)

MCF:	102144258(CYP3A8)

CSAB:

103246766

RRO:

104673585

RBB:

108538168

CJC:	100404344(CYP3A4)

SBQ:

101037403

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

Other DBs

ExplorEnz - The Enzyme Database:

1.14.14.57

IUBMB Enzyme Nomenclature:

1.14.14.57

ExPASy - ENZYME nomenclature database:

1.14.14.57

BRENDA, the Enzyme Database:

1.14.14.57

CAS:	105669-85-0

All links

Chemical substance (8)   
   KEGG COMPOUND (8)   
Chemical reaction (4)   
   KEGG REACTION (2)   
   KEGG RCLASS (2)   
Gene (16)   
   KEGG ORTHOLOGY (2)   
   KEGG GENES (14)   
Protein sequence (4)   
   UniProt (2)   
   SWISS-PROT (1)   
   RefSeq(pep) (1)   
DNA sequence (2)   
   RefSeq(nuc) (1)   
   EMBL (1)   
Protein domain (4)   
   InterPro (4)   
All databases (38)   

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