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1.14.14.16: steroid 21-monooxygenase

This is an abbreviated version!
For detailed information about steroid 21-monooxygenase, go to the full flat file.

Word Map on EC 1.14.14.16

Reaction

a C21 steroid
+
[reduced NADPH-hemoprotein reductase]
+
O2
=
a 21-hydroxy-C21-steroid
+
[oxidized NADPH-hemoprotein reductase]
+
H2O

Synonyms

17alpha-hydroxyprogesterone 21-hydrolase, 21-hydroxylase, 21-hydroxylase cytochrome P-450, 21OH, C3B21RA protein, CYP21, CYP21A2, CYP2D, Cytochrome P-450 specific for steroid C-21 hydroxylation, cytochrome P-450-linked mixed function oxidase system, cytochrome P-450C-21, cytochrome p450 21A2, cytochrome P450 steroid 21-hydroxylase, cytochrome P450c21, EC 1.14.1.8, EC 1.14.99.10, EC 1.99.1.11, P-450(C21), P450 oxidoreductase-21-hydroxylase, P450-C21, P450-C21B, P450c21, Progesterone 21-hydroxylase, Steroid 21-hydroxylase, steroid 21-hydroxylase system, steroid 21-hydroxylation system, steroid cytochrome P450 21-hydroxylase

ECTree

     1 Oxidoreductases
         1.14 Acting on paired donors, with incorporation or reduction of molecular oxygen
             1.14.14 With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor
                1.14.14.16 steroid 21-monooxygenase

Reference

Reference on EC 1.14.14.16 - steroid 21-monooxygenase

Please use the Reference Search for a specific query.
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Ryan, K.J.; Engel, L.L.
Hydroxylation of steroids at carbon 21
J. Biol. Chem.
225
103-114
1957
Bos taurus
Manually annotated by BRENDA team
Hiwatashi, A.; Ichikawa, Y.
Purification and reconstitution of the steroid 21-hydroxylase system (cytochrome P-450-linked mixed function oxidase system) of bovine adrenocortical microsomes
Biochim. Biophys. Acta
664
33-48
1981
Bos taurus
Manually annotated by BRENDA team
Greenfield, N.; Ponticorvo, L.; Chasalow, F.; Lieberman, S.
Activation and Inhibition of the adrenal steroid 21-hydroxylation system by cytosolic constituents: influence of glutathione, glutathione reductase, and ascorbate
Arch. Biochem. Biophys.
200
232-244
1980
Bos taurus
Manually annotated by BRENDA team
Haniu, M.; Yanagibashi, K.; Hall, P.F.; Shively, J.E.
Complete amino acid sequence of 21-hydroxylase cytochrome p-450 from porcine adrenal mircosomes
Arch. Biochem. Biophys.
254
380-384
1987
Sus scrofa
Manually annotated by BRENDA team
Narasimhulu, S.; Eddy, C.R.
Adrenal microsomal hydroxylating system: purification and substrate binduing properties of cytochrome P-450C-21
Biochemistry
24
4287-4294
1985
Bos taurus
Manually annotated by BRENDA team
Blom, S.; Förlin, L.; Andersson, T.B.
Characterisation of head kidney and liver microsomal 17-hydroxyprogesterone 21-hydrolase activity in rainbow trout (Oncorhynchus mykiss) and the lack of regulatory effects of ACTH
Fish Physiol. Biochem.
24
1-8
2001
Oncorhynchus mykiss
-
Manually annotated by BRENDA team
Belanger, A.; Tremblay, Y.; Vallee, M.; Provencher, P.H.; Perron, S.
Regulation of 21 hydroxylase activity by steroids
Endocr. Res.
21
329-41
1995
Bos taurus
Manually annotated by BRENDA team
Yuan, P.M.; Nakajin, S.; Haniu, M.; Shinoda, M.; Hall, P.F.; Shively, J.E.
Steroid 21-hydroxylase (cytochrome P-450) from porcine adrenocorticla microsomes: microsequence analysis of cysteine-containing peptides
Biochemistry
22
143-149
1983
Sus scrofa
Manually annotated by BRENDA team
Kominami, S.; Ochi, H.; Kobayashi, Y.; Takemori, S.
Studies on the steroid hydroxylation system in adrenal cortex microsomes
J. Biol. Chem.
255
3386-3394
1980
Bos taurus
Manually annotated by BRENDA team
Bumpus, J.A.; Dus, K.
Bovine adrenocortical microsomal hemeproteins P-45017alpha and P-450C-21: Isolation, partial characterization, and comparison to P-450SCC
J. Biol. Chem.
257
12696-12704
1982
Bos taurus
Manually annotated by BRENDA team
Higashi, Y; Yoshioka, H.; Yamane, M.; Gotoh, O.; Fuji-Kuriyama, Y.
complete nucleotide sequence of two steroid 21-hydroxylase genes tandemly arranged in human chromosomes: a pseudogene and a genuine gene
Proc. Natl. Acad. Sci. USA
83
2841-2845
1986
Homo sapiens
Manually annotated by BRENDA team
Lovelace, M.; Watson, T.G.; Stephenson, G.L.
Steroid 21-hydroxylase expression in cultured rat astrocytes
Brain Res. Bull.
61
609-615
2003
Rattus norvegicus
Manually annotated by BRENDA team
Kishimoto, W.; Hiroi, T.; Shiraishi, M.; Osada, M.; Imaoka, S.; Kominami, S.; Igarashi, T.; Funae, Y.
Cytochrome P450 2D catalyze steroid 21-hydroxylation in the brain
Endocrinology
145
699-705
2004
Rattus norvegicus
Manually annotated by BRENDA team
Barbaro, M.; Lajic, S.; Baldazzi, L.; Balsamo, A.; Pirazzoli, P.; Cicognani, A.; Wedell, A.; Cacciari, E.
Functional analysis of two recurrent amino acid substitutions in the CYP21 gene from Italian patients with congenital adrenal hyperplasia
J. Clin. Endocrinol. Metab.
89
2402-2407
2004
Homo sapiens
Manually annotated by BRENDA team
Li, Y.Y.; Inoue, K.; Takei, Y.
Interrenal steroid 21-hydroxylase in eels: primary structure, progesterone-specific activity and enhanced expression by ACTH
J. Mol. Endocrinol.
31
327-340
2003
Anguilla japonica
Manually annotated by BRENDA team
Felix-Lopez, X.; Riba, L.; Ordonez-Sanchez, M.L.; Ramirez-Jimenez, S.; Ventura-Gallegos, J.L.; Zentella-Dehesa, A.; Tusie-Luna, M.T.
Steroid 21-hydroxylase (P450c21) naturally occurring mutants I172N, V281L and I236N/V237E/M239K exert a dominant negative effect on enzymatic activity when co-expressed with the wild-type protein
J. Pediatr. Endocrinol. Metab.
16
1017-1024
2003
Homo sapiens
Manually annotated by BRENDA team
Martineau, I.; Belanger, A.; Tchernof, A.; Tremblay, Y.
Molecular cloning and expression of guinea pig cytochrome P450c21 cDNA (steroid 21-hydroxylase) isolated from the adrenals
J. Steroid Biochem. Mol. Biol.
86
123-132
2003
Cavia porcellus
Manually annotated by BRENDA team
Arase, M.; Waterman, M.R.; Kagawa, N.
Purification and characterization of bovine steroid 21-hydroxylase (P450c21) efficiently expressed in Escherichia coli
Biochem. Biophys. Res. Commun.
344
400-405
2006
Bos taurus (P00191), Bos taurus
Manually annotated by BRENDA team
Miguel, R.N.; Chen, S.; Nikfarjam, L.; Kominami, S.; Carpenter, B.; Dal Pra, C.; Betterle, C.; Zanchetta, R.; Nakamatsu, T.; Powell, M.; Hewer, R.; Blundell, T.L.; Smith, B.R.; Furmaniak, J.
Analysis of the interaction between human steroid 21-hydroxylase and various monoclonal antibodies using comparative structural modelling
Eur. J. Endocrinol.
153
949-961
2005
Homo sapiens
Manually annotated by BRENDA team
Dolzan, V.; Solyom, J.; Fekete, G.; Kovacs, J.; Rakosnikova, V.; Votava, F.; Lebl, J.; Pribilincova, Z.; Baumgartner-Parzer, S.M.; Riedl, S.; Waldhauser, F.; Frisch, H.; Stopar-Obreza, M.; Krzisnik, C.; Battelino, T.
Mutational spectrum of steroid 21-hydroxylase and the genotype-phenotype association in Middle European patients with congenital adrenal hyperplasia
Eur. J. Endocrinol.
153
99-106
2005
Homo sapiens
Manually annotated by BRENDA team
Supornsilchai, V.; Svechnikov, K.; Seidlova-Wuttke, D.; Wuttke, W.; Soeder, O.
Phytoestrogen resveratrol suppresses steroidogenesis by rat adrenocortical cells by inhibiting cytochrome P450 c21-hydroxylase
Horm. Res.
64
280-286
2005
Rattus norvegicus
Manually annotated by BRENDA team
Krone, N.; Riepe, F.G.; Groetzinger, J.; Partsch, C.; Braemswig, J.; Sippell, W.G.
The residue E351 is essential for the activity of human 21-hydroxylase: evidence from a naturally occurring novel point mutation compared with artificial mutants generated by single amino acid substitutions
J. Mol. Med.
83
561-568
2005
Homo sapiens
Manually annotated by BRENDA team
Barbaro, M.; Baldazzi, L.; Balsamo, A.; Lajic, S.; Robins, T.; Barp, L.; Pirazzoli, P.; Cacciari, E.; Cicognani, A.; Wedell, A.
Functional studies of two novel and two rare mutations in the 21-hydroxylase gene
J. Mol. Med.
84
521-528
2006
Homo sapiens
Manually annotated by BRENDA team
Trinh, L.; Nimkarn, S.; New, M.I.; Lin-Su, K.
Growth and pubertal characteristics in patients with congenital adrenal hyperplasia due to 21-hydroxylase deficiency
J. Pediatr. Endocrinol. Metab.
20
883-891
2007
Homo sapiens
Manually annotated by BRENDA team
Soardi, F.C.; Lemos-Marini, S.H.; Coeli, F.B.; Maturana, V.G.; Silva, M.D.; Bernardi, R.D.; Justo, G.Z.; de-Mello, M.P.
Heterozygosis for CYP21A2 mutation considered as 21-hydroxylase deficiency in neonatal screening
Arq. Bras. Endocrinol. Metabol.
52
1388-1392
2008
Homo sapiens
Manually annotated by BRENDA team
Concolino, P.; Mello, E.; Minucci, A.; Giardina, E.; Zuppi, C.; Toscano, V.; Capoluongo, E.
A new CYP21A1P/CYP21A2 chimeric gene identified in an Italian woman suffering from classical congenital adrenal hyperplasia form
BMC Med. Genet.
10
72
2009
Homo sapiens (P08686), Homo sapiens
Manually annotated by BRENDA team
Ono, M.; Kashimada, K.; Miyai, K.; Onishi, T.; Takagi, M.; Honma, S.; Mizutani, S.
In vitro enzyme assay of CYP21A2 mutation (R483Q) by a novel method using liquid chromatography-electrospray ionization tandem mass spectrometry (LC-ESI-MS/MS)
Clin. Pediatr. Endocrinol.
17
49-56
2008
Homo sapiens
Manually annotated by BRENDA team
Marques, C.J.; Pignatelli, D.; Carvalho, B.; Barcelo, J.; Almeida, A.C.; Fernandes, S.; Witchel, S.F.; Sousa, M.; Oliveira, M.J.; Freitas, P.; Fontoura, M.; Carvalho, D.; Barros, A.; Carvalho, F.
Mutational characterization of steroid 21-hydroxylase gene in Portuguese patients with congenital adrenal hyperplasia
Exp. Clin. Endocrinol. Diabetes
118
505-512
2010
Homo sapiens (P08686), Homo sapiens
Manually annotated by BRENDA team
Bleicken, C.; Loidi, L.; Dhir, V.; Parajes, S.; Quinteiro, C.; Dominguez, F.; Groetzinger, J.; Sippell, W.G.; Riepe, F.G.; Arlt, W.; Krone, N.
Functional characterization of three CYP21A2 sequence variants (p.A265V, p.W302S, p.D322G) employing a yeast co-expression system
Hum. Mutat.
30
E443-E450
2009
Homo sapiens
Manually annotated by BRENDA team
Bratland, E.; Bredholt, G.; Mellgren, G.; Knappskog, P.M.; Mozes, E.; Husebye, E.S.
The purification and application of biologically active recombinant steroid cytochrome P450 21-hydroxylase: the major autoantigen in autoimmune Addisons disease
J. Autoimmun.
33
58-67
2009
Homo sapiens (P08686), Homo sapiens
Manually annotated by BRENDA team
Tosha, T.; Kagawa, N.; Arase, M.; Waterman, M.; Kitagawa, T.
Interaction between substrate and oxygen ligand responsible for effective O-O bond cleavage in bovine cytochrome P450 steroid 21-hydroxylase proved by Raman spectroscopy
J. Biol. Chem.
283
3708-3717
2008
Bos taurus
Manually annotated by BRENDA team
Dubey, S.; Idicula-Thomas, S.; Anwaruddin, M.; Saravanan, C.; Varma, R.R.; Maitra, A.
A novel 9-bp insertion detected in steroid 21-hydroxylase gene (CYP21A2): prediction of its structural and functional implications by computational methods
J. Biomed. Sci.
16
3-3
2009
Homo sapiens (P08686), Homo sapiens
Manually annotated by BRENDA team
Riepe, F.G.; Hiort, O.; Groetzinger, J.; Sippell, W.G.; Krone, N.; Holterhus, P.M.
Functional and structural consequences of a novel point mutation in the CYP21A2 gene causing congenital adrenal hyperplasia: potential relevance of helix C for P450 oxidoreductase-21-hydroxylase interaction
J. Clin. Endocrinol. Metab.
93
2891-2895
2008
Homo sapiens
Manually annotated by BRENDA team
Bratland, E.; Skinningsrud, B.; Undlien, D.E.; Mozes, E.; Husebye, E.S.
T cell responses to steroid cytochrome P450 21-hydroxylase in patients with autoimmune primary adrenal insufficiency
J. Clin. Endocrinol. Metab.
94
5117-5124
2009
Homo sapiens
Manually annotated by BRENDA team
Rottembourg, D.; Deal, C.; Lambert, M.; Mallone, R.; Carel, J.C.; Lacroix, A.; Caillat-Zucman, S.; le Deist, F.
21-Hydroxylase epitopes are targeted by CD8 T cells in autoimmune Addisons disease
J. Autoimmun.
35
309-315
2010
Homo sapiens (P08686), Homo sapiens
Manually annotated by BRENDA team
Zehentgruber, D.; Dragan, C.A.; Bureik, M.; Luetz, S.
Challenges of steroid biotransformation with human cytochrome P450 monooxygenase CYP21 using resting cells of recombinant Schizosaccharomyces pombe
J. Biotechnol.
146
179-185
2010
Homo sapiens (P08686), Homo sapiens
Manually annotated by BRENDA team
Gaffney, D.; Howie, A.; Bakkush, A.; Hoffmann, T.; Mason, J.; Wallace, A.; Donaldson, M.
Functional characterisation of the H365Y mutation of the 21-hydroxylase gene in congenital adrenal hyperplasia
J. Steroid Biochem. Mol. Biol.
123
109-114
2011
Homo sapiens
Manually annotated by BRENDA team
Sushko, T.A.; Gilep, A.A.; Usanov, S.A.
Mechanism of intermolecular interactions of microsomal cytochrome P450s CYP17 and CYP21 involved in steroid hormone biosynthesis
Biochemistry (Moscow)
77
585-592
2012
Homo sapiens
Manually annotated by BRENDA team
Mizrachi, D.; Wang, Z.; Sharma, K.K.; Gupta, M.K.; Xu, K.; Dwyer, C.R.; Auchus, R.J.
Why human cytochrome P450c21 is a progesterone 21-hydroxylase
Biochemistry
50
3968-3974
2011
Homo sapiens (P08686), Homo sapiens
Manually annotated by BRENDA team
Yoshimoto, F.K.; Zhou, Y.; Peng, H.M.; Stidd, D.; Yoshimoto, J.A.; Sharma, K.K.; Matthew, S.; Auchus, R.J.
Minor activities and transition state properties of the human steroid hydroxylases cytochromes P450c17 and P450c21, from reactions observed with deuterium-labeled substrates
Biochemistry
51
7064-7077
2012
Homo sapiens
Manually annotated by BRENDA team
Zhao, B.; Lei, L.; Kagawa, N.; Sundaramoorthy, M.; Banerjee, S.; Nagy, L.D.; Guengerich, F.P.; Waterman, M.R.
Three-dimensional structure of steroid 21-hydroxylase (cytochrome P450 21A2) with two substrates reveals locations of disease-associated variants
J. Biol. Chem.
287
10613-10622
2012
Bos taurus (P00191), Bos taurus, Homo sapiens (P08686)
Manually annotated by BRENDA team
Yoshimoto, F.K.; Desilets, M.C.; Auchus, R.J.
Synthesis of halogenated pregnanes, mechanistic probes of steroid hydroxylases CYP17A1 and CYP21A2
J. Steroid Biochem. Mol. Biol.
128
38-50
2012
Homo sapiens
Manually annotated by BRENDA team
Haider, S.; Islam, B.; DAtri, V.; Sgobba, M.; Poojari, C.; Sun, L.; Yuen, T.; Zaidi, M.; New, M.I.
Structure-phenotype correlations of human CYP21A2 mutations in congenital adrenal hyperplasia
Proc. Natl. Acad. Sci. USA
110
2605-2610
2013
Homo sapiens (P08686), Homo sapiens
Manually annotated by BRENDA team
Parr, M.K.; Zoellner, A.; Fusshoeller, G.; Opfermann, G.; Schloerer, N.; Zorio, M.; Bureik, M.; Schaenzer, W.
Unexpected contribution of cytochrome P450 enzymes CYP11B2 and CYP21, as well as CYP3A4 in xenobiotic androgen elimination - insights from metandienone metabolism
Toxicol. Lett.
213
381-391
2012
Homo sapiens
Manually annotated by BRENDA team
Pallan, P.S.; Wang, C.; Lei, L.; Yoshimoto, F.K.; Auchus, R.J.; Waterman, M.R.; Guengerich, F.P.; Egli, M.
Human cytochrome P450 21A2, the major steroid 21-hydroxylase: structure of the enzyme-progesterone substrate complex and rate-limiting C-H bond cleavage
J. Biol. Chem.
290
13128-13143
2015
Bos taurus (P00191), Bos taurus, Homo sapiens (P08686), Homo sapiens
Manually annotated by BRENDA team
Doleschall, M.; Szabo, J.A.; Pazmandi, J.; Szilagyi, A.; Koncz, K.; Farkas, H.; Toth, M.; Igaz, P.; Glaz, E.; Prohaszka, Z.; Korbonits, M.; Racz, K.; Fuest, G.; Patocs, A.
Common genetic variants of the human steroid 21-hydroxylase gene (CYP21A2) are related to differences in circulating hormone levels
PLoS ONE
9
e107244
2014
Homo sapiens (P08686), Homo sapiens
Manually annotated by BRENDA team
Yoshimoto, F.K.; Peng, H.M.; Zhang, H.; Anderson, S.M.; Auchus, R.J.
Epoxidation activities of human cytochromes P450c17 and P450c21
Biochemistry
53
7531-7540
2014
Homo sapiens (P08686), Homo sapiens
Manually annotated by BRENDA team
Wang, C.; Pallan, P.S.; Zhang, W.; Lei, L.; Yoshimoto, F.K.; Waterman, M.R.; Egli, M.; Guengerich, F.P.
Functional analysis of human cytochrome P450 21A2 variants involved in congenital adrenal hyperplasia
J. Biol. Chem.
292
10767-10778
2017
Homo sapiens (P08686), Homo sapiens
Manually annotated by BRENDA team
Pallan, P.S.; Lei, L.; Wang, C.; Waterman, M.R.; Guengerich, F.P.; Egli, M.
Research Resource Correlating human cytochrome P450 21A2 crystal structure and phenotypes of mutations in congenital adrenal hyperplasia
Mol. Endocrinol.
29
1375-1384
2015
Homo sapiens (P08686), Homo sapiens
Manually annotated by BRENDA team