KEGG ENZYME: 1.14.14.178

ENZYME: 1.14.14.178

Entry

EC 1.14.14.178              Enzyme

Name

steroid 22S-hydroxylase;
CYP90B1 (gene name);
DWF4 (gene name);
steroid C-22 hydroxylase

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

steroid,NADPH---hemoprotein reductase:oxygen 22S-oxidoreductase (hydroxylating)

Reaction(IUBMB)

(1) a C27 steroid + O2 + [reduced NADPH---hemoprotein reductase] = a (22S)-22-hydroxy-C27 steroid + 2 H2O + [oxidized NADPH---hemoprotein reductase];
(2) a C28 steroid + O2 + [reduced NADPH---hemoprotein reductase] = a (22S)-22-hydroxy-C28 steroid + 2 H2O + [oxidized NADPH---hemoprotein reductase];
(3) a C29 steroid + O2 + [reduced NADPH---hemoprotein reductase] = a (22S)-22-hydroxy-C29 steroid + 2 H2O + [oxidized NADPH---hemoprotein reductase]

Reaction(KEGG)

(other) R07445 R07452 R07453 R07454

Substrate

C27 steroid;
O2 [CPD:C00007];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
C28 steroid;
C29 steroid

Product

(22S)-22-hydroxy-C27 steroid;
H2O [CPD:C00001];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
(22S)-22-hydroxy-C28 steroid;
(22S)-22-hydroxy-C29 steroid

Comment

This plant cytochrome P-450 (heme thiolate) enzyme participates in the biosynthesis of brassinosteroids. While in vivo substrates include C28 steroids such as campestanol, campesterol, and 6-oxocampestanol, the enzyme is able to catalyse the C-22 hydroxylation of a variety of C27, C28 and C29 steroids.

History

EC 1.14.14.178 created 2022

Pathway

ec00905

Brassinosteroid biosynthesis

ec01100

Metabolic pathways

ec01110

Biosynthesis of secondary metabolites

Orthology

K09587

steroid 22S-hydroxylase

K12639

steroid 22S-hydroxylase

Genes

ATH:	AT3G50660(DWF4) AT5G14400(CYP724A1)

ALY:	9307686 9312109

CRB:	17882948 17885187

CSAT:

104769675 104780889 104791284

EUS:	EUTSA_v10011005mg EUTSA_v10015753mg

BRP:	103828198 103840968 103846487 103850927

BNA:	106364625 106370550 106401625 106405681 106417880 106447365 125575243

BOE:	106310362 106317102 106321383 106326221

RSZ:	108809973 108816728 108826420 108841135

THJ:	104802390 104819220 104826953

CPAP:

110808733 110808955 110822261

CIT:	102607509 102623486 102625685

CIC:	CICLE_v10015033mg CICLE_v10017470mg CICLE_v10025451mg

PVY:	116113019 116113135 116118304 116118306 116142804

MINC:

123195983 123199643 123199686 123214950 123216538 123222469

TCC:	18600875 18610945 18612531

GRA:	105779232 105803387 105803806

GHI:	107896149 107912480 107913065 107922960 107926035 107961481

GAB:	108460073 108471227 108472771

HSYR:

120138551 120139008 120139083 120139225 120171780 120196689 120207285

DZI:	111292390 111292725 111300505 111301072 111306191 111313510 111316237

EGR:	104419198 104419755 104420630

RARG:

115736315 115751149

GMX:	100789515 100791737 100800210 100802498

GSJ:	114377375 114382291 114389140 114420632

PVU:	137805971 137810217 137826213

VRA:	106765911 106778030

VAR:	108334671 108335822

VUN:	114166425 114179641

VUM:	124824410 124826501

CCAJ:

109793322 109801635 109810494

APRC:

113859349 113859482 113868805

MTR:	11405189 11408048 11437159

TPRA:

123893165 123908684 123920823

CAM:	101499755 101500152

PSAT:

127120259 127128065 127135353

VVO:	131608124 131608206 131611415 131652102

LJA:	130729604 130735197 130740729

ADU:

107487855

AIP:

107642870

AHF:	112749146 112800701

LANG:

109331920 109348687 109350644

PCIN:

129304416 129310431 129321868

QSA:	O6P43_004724 O6P43_008869 O6P43_024752 O6P43_033718

FVE:	101296274 101304220 101308903

AANS:

126797329 126799841 126799884

RCN:	112183385 112187887 112187901

PPER:

18770032 18782463 18784320

PMUM:

103329118 103330155 103340078

PAVI:

110755657 110756001 110773452

PDUL:

117621138 117622631 117635807

MDM:	103401164 103401541 103405248 103429004 103442738

MSYL:

126604824 126609819 126613856 126634408 126634409

PXB:	103941521 103951781 103960819

PCOX:

137734180 137738846 137748588 137749357

ZJU:	107408382 107415219 107415245 107416825

MNT:	21395422 21400684

CSAV:

115699387 115700900 115714415

CSV:	101211854 101215045

CMO:	103494380 103498124

BHJ:	120069803 120079590

MCHA:

111006083 111008332

CMAX:

111479953 111487092

CMOS:

111430228 111446972

CPEP:

111807994 111808675

RCU:	8260354 8273425 8288322

MEAN:

126654736 126679451

JCU:	105634541 105643410

HBR:	110634320 110654062 110656526 110665021 110671515

MESC:

110602755 110603714 110605043 110629477

POP:	18099286 18101214 7467663 7469349

PEU:	105110409 105116030 105116836 105126568

PALZ:

118030029 118054146 118058119 118063301

PNZ:	133672985 133682741 133686308 133694172

JRE:	108995250 108997500 109009656

CILL:

122297006 122303891 122307498

CAVE:

132180925 132183139 132188356

AGLU:

133861134 133861314 133864929

QSU:	111993132 111999072 112006212 112023948

QLO:	115978378 115987302 115994961

TWL:	120000980 120011489 120014527

VVI:	100241065 100245690 100257922

VRI:	117913676 117926615 117931086

SLY:	101251900(CYP724B2) 101256342(CYP90B3) 101265305

SPEN:

107009445 107010789 107024375

SOT:	102582442 102603786

SSTN:

125847510 125847511 125849264 125877193

SDUL:

129872791 129875101 129892009

CANN:

107858413 107859954 107877366

LBB:	132614523 132618813 132623588 132624769

NTA:	107776917 107779615 107795428 107795954 107801070 107825897

NSY:	104210061 104212166 104243183

NTO:	104100965 104104628 104115826

NAU:	109207893 109210801 109217467 109221822

INI:	109158109 109168575 109187712

ITR:	115998915 116011467 116011693

SIND:

105176862 105177981 105179881

OEU:	111367619 111380525 111389155

EGT:	105954961 105970780 105976276

SSPL:

121767277 121772586 121774314 121802385 121806412 121809027

SMIL:

130987520 130989157 131012201 131019837

SHIS:

125194913 125196523 125202713

APAN:

127240119 127248819 127258082

HAN:	110895233 110915264

ECAD:

122579500 122598110

LSV:	111883587 111918657

CCAV:

112513520 112516322

DCR:	108220768 108221483 108224415 108227649

CSIN:

114274957 114316234 114318951

RVL:	131304095 131330247 131336713

AEW:	130751713 130768547 130783325

DLT:	127792213 127804593 127805040

BVG:

104895859

SOE:

110797811

CQI:	110686172 110722522

ATRI:

130807369

MOF:	131162668 131168519

NNU:	104591542 104595706 104601879 104608289

MING:

122073840 122078302 122083658 122094194

TSS:	122638371 122640557 122654025 122658580 122661166

PSOM:

113273094 113285824 113289235 113293814 113301538

OSA:	4332134(CYP90B2) 4336116(CYP724B1)

DOSA:

Os03g0227700 Os04g0469800

OBR:	102709630 102717238

OGL:	127768703 127769428

BDI:	100833643 100837605

ATS:	109734230 109742297 109786179

TDC:	119273638 119285031 119291093 119355441 119364561

TAES:

123045717 123053590 123059596 123066933 123075890 123085252 123092868 123098154 123189488

TUA:	125526986 125549501 125552395

LPER:

127296297 127335210

LRD:	124678232 124678291 124701853 124701863

SBI:	8055423 8056846 8058684

ZMA:	100191562 100217085

MFLO:

136463684 136470206 136474024 136493771 136494356 136496856 136549077 136549421

SITA:

101768860 101769663 101770693

SVS:	117841038 117855539 117865849

PVIR:

120641205 120646755 120652021 120683428 120688207 120691708

PHAI:

112874677 112875152 112901555

PAUA:

133888713 133911973 133916580 133917948 133923541

PDA:	103697967 103704238 103707598 103707601 103721661 120113249

EGU:	105055939 105058149 105060750 105060809

MUS:	103974765 103983905 135609829 135619928 135619929

ZOF:	122008713 122011363 122013395 122014363 122015895 122026256 122026454 122027838 122028682 122030413 122030415 122032511 122034945 122045268

DCT:	110092799 110112973 110114079 110114986

PEQ:	110019548 110025965

AOF:	109833124 109834320 109834432 109840188

MSIN:

131229250 131246152 131257872

ACAK:

137941534 137950894 137951988 137953759 137962072

NCOL:

116249569 116259560 116260033

ATR:	18445832 18447481 18448244

CJF:	131026863 131030354 131033523 131035135 131044643

» show all

Reference

1 [PMID:11319239]

Authors

Asami T, Mizutani M, Fujioka S, Goda H, Min YK, Shimada Y, Nakano T, Takatsuto S, Matsuyama T, Nagata N, Sakata K, Yoshida S.

Title

Selective interaction of triazole derivatives with DWF4, a cytochrome P450 monooxygenase of the brassinosteroid biosynthetic pathway, correlates with brassinosteroid deficiency in planta.

Journal

J Biol Chem 276:25687-91 (2001)
DOI:10.1074/jbc.M103524200

Reference

2 [PMID:11489171]

Authors

Choe S, Fujioka S, Noguchi T, Takatsuto S, Yoshida S, Feldmann KA.

Title

Overexpression of DWARF4 in the brassinosteroid biosynthetic pathway results in increased vegetative growth and seed yield in Arabidopsis.

Journal

Plant J 26:573-82 (2001)
DOI:10.1046/j.1365-313x.2001.01055.x

Sequence

[ath:AT3G50660]

Reference

3 [PMID:12350224]

Authors

Asami T, Mizutani M, Shimada Y, Goda H, Kitahata N, Sekimata K, Han SY, Fujioka S, Takatsuto S, Sakata K, Yoshida S.

Title

Triadimefon, a fungicidal triazole-type P450 inhibitor, induces brassinosteroid deficiency-like phenotypes in plants and binds to DWF4 protein in the brassinosteroid biosynthesis pathway.

Journal

Biochem J 369:71-6 (2003)
DOI:10.1042/BJ20020835

Reference

4 [PMID:16460510]

Authors

Fujita S, Ohnishi T, Watanabe B, Yokota T, Takatsuto S, Fujioka S, Yoshida S, Sakata K, Mizutani M.

Title

Arabidopsis CYP90B1 catalyses the early C-22 hydroxylation of C27, C28 and C29 sterols.

Journal

Plant J 45:765-74 (2006)
DOI:10.1111/j.1365-313X.2005.02639.x

Reference

5 [PMID:16960392]