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O22203 (C98A3_ARATH) Reviewed, UniProtKB/Swiss-Prot

Last modified April 16, 2014. Version 118. Feed History...

Clusters with 100%, 90%, 50% identity | Documents (2) | Third-party data text xml rdf/xml gff fasta
to top of pageNames·Attributes·General annotation·Ontologies·Sequence annotation·Sequences·References·Cross-refs·Entry info·DocumentsCustomize order

Names and origin

Protein namesRecommended name:
Cytochrome P450 98A3

EC=1.14.-.-
Alternative name(s):
Protein REDUCED EPIDERMAL FLUORESCENCE 8
p-coumaroylshikimate/quinate 3'-hydrolxylase
Short name=C3'H
Gene names
Name:CYP98A3
Synonyms:C3'H, REF8
Ordered Locus Names:At2g40890
ORF Names:T20B5.9
OrganismArabidopsis thaliana (Mouse-ear cress) [Reference proteome]
Taxonomic identifier3702 [NCBI]
Taxonomic lineageEukaryotaViridiplantaeStreptophytaEmbryophytaTracheophytaSpermatophytaMagnoliophytaeudicotyledonsGunneridaePentapetalaerosidsmalvidsBrassicalesBrassicaceaeCamelineaeArabidopsis

Protein attributes

Sequence length508 AA.
Sequence statusComplete.
Protein existenceEvidence at protein level

General annotation (Comments)

Function

Cytochrome P450 which catalyzes 3'-hydroxylation of p-coumaric esters of shikimic/quinic acids to form lignin monomers. Can use p-coumarate, p-coumaraldehyde, p-coumaroyl methyl ester, 5-O-(4-coumaroyl) D-quinate and 5-O-(4-coumaroyl) shikimate as substrates, but not p-coumaryl alcohol, p-coumaroyl CoA, 1-O-p-coumaroyl-beta-D-glucose, p-hydroxy-cinnamyl alcohol, cinnamate, caffeate or ferulate. Has a weak activity on tri(p-coumaroyl)spermidine, but none on triferuloylspermidine. Hydroxylates preferentially the 5-O-isomer, but can also convert the 4-O- and 3-O-isomers with a lower efficiency. Involved in the biosynthesis of the coumarins scopoletin and scopolin. Essential for the biosynthesis of lignin. Ref.5 Ref.6 Ref.7 Ref.8 Ref.9

Cofactor

Heme group By similarity.

Subcellular location

Membrane; Single-pass membrane protein Potential.

Tissue specificity

Highly expressed in stems, roots and siliques. Detected in leaves flowers and seedlings. Highest expression detected in differentiating xylem. Ref.5 Ref.6 Ref.11

Induction

Up-regulated by wounding. Ref.5

Disruption phenotype

Dwarf. 91% and 97% reduction of the levels of scopoletin and scopolin respectively, but increased levels of skimmin, the beta-glucoside of umbelliferone. Altered lignin composition and increased susceptiblity to fungal colonization. Ref.7 Ref.8 Ref.9

Sequence similarities

Belongs to the cytochrome P450 family.

Biophysicochemical properties

Kinetic parameters:

Kcat is 612 min(-1) with 5-O-(4-coumaroyl) shikimate as substrate (Ref.5). Kcat is 399 min(-1) with 5-O-(4-coumaroyl) quinate as substrate (Ref.5).

KM=7 µM for 5-O-(4-coumaroyl) shikimate Ref.5

KM=18 µM for 5-O-(4-coumaroyl) quinate

Sequence caution

The sequence AAB86449.2 differs from that shown. Reason: Erroneous initiation. Translation N-terminally extended.

Ontologies

Keywords
   Cellular componentMembrane
   DomainTransmembrane
Transmembrane helix
   LigandHeme
Iron
Metal-binding
   Molecular functionMonooxygenase
Oxidoreductase
   PTMIsopeptide bond
Ubl conjugation
   Technical termComplete proteome
Reference proteome
Gene Ontology (GO)
   Biological_processcoumarin biosynthetic process

Inferred from mutant phenotype Ref.8. Source: TAIR

flavonoid biosynthetic process

Inferred from mutant phenotype Ref.9. Source: TAIR

lignin biosynthetic process

Inferred from mutant phenotype Ref.9. Source: TAIR

phenylpropanoid biosynthetic process

Inferred from mutant phenotype Ref.5Ref.9. Source: TAIR

   Cellular_componentendoplasmic reticulum

Inferred from direct assay PubMed 16618929PubMed 22923678PubMed 23175744. Source: TAIR

integral component of membrane

Inferred from electronic annotation. Source: UniProtKB-KW

intracellular membrane-bounded organelle

Inferred from direct assay Ref.5. Source: TAIR

mitochondrion

Inferred from direct assay PubMed 15276431. Source: TAIR

plasma membrane

Inferred from direct assay PubMed 17317660. Source: TAIR

   Molecular_functionheme binding

Inferred from electronic annotation. Source: InterPro

identical protein binding

Inferred from physical interaction PubMed 23175744. Source: TAIR

iron ion binding

Inferred from electronic annotation. Source: InterPro

monooxygenase activity

Inferred from direct assay Ref.5. Source: TAIR

oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen

Inferred from electronic annotation. Source: InterPro

p-coumarate 3-hydroxylase activity

Inferred from direct assay Ref.5. Source: TAIR

Complete GO annotation...

Sequence annotation (Features)

Feature keyPosition(s)LengthDescriptionGraphical viewFeature identifier

Molecule processing

Chain1 – 508508Cytochrome P450 98A3
PRO_0000052199

Regions

Transmembrane1 – 2121Helical; Potential

Sites

Metal binding4381Iron (heme axial ligand) By similarity

Amino acid modifications

Cross-link172Glycyl lysine isopeptide (Lys-Gly) (interchain with G-Cter in ubiquitin) Ref.10
Cross-link189Glycyl lysine isopeptide (Lys-Gly) (interchain with G-Cter in ubiquitin) Ref.10

Experimental info

Mutagenesis4441G → D in ref8; loss of activity. Ref.6
Sequence conflict2021G → E in AAL06992. Ref.3
Sequence conflict4661G → V in BAE98524. Ref.4

Sequences

Sequence LengthMass (Da)Tools
O22203 [UniParc].

Last modified January 1, 1998. Version 1.
Checksum: BD22A574F6B16C35

FASTA50857,927
        10         20         30         40         50         60 
MSWFLIAVAT IAAVVSYKLI QRLRYKFPPG PSPKPIVGNL YDIKPVRFRC YYEWAQSYGP 

        70         80         90        100        110        120 
IISVWIGSIL NVVVSSAELA KEVLKEHDQK LADRHRNRST EAFSRNGQDL IWADYGPHYV 

       130        140        150        160        170        180 
KVRKVCTLEL FTPKRLESLR PIREDEVTAM VESVFRDCNL PENRAKGLQL RKYLGAVAFN 

       190        200        210        220        230        240 
NITRLAFGKR FMNAEGVVDE QGLEFKAIVS NGLKLGASLS IAEHIPWLRW MFPADEKAFA 

       250        260        270        280        290        300 
EHGARRDRLT RAIMEEHTLA RQKSSGAKQH FVDALLTLKD QYDLSEDTII GLLWDMITAG 

       310        320        330        340        350        360 
MDTTAITAEW AMAEMIKNPR VQQKVQEEFD RVVGLDRILT EADFSRLPYL QCVVKESFRL 

       370        380        390        400        410        420 
HPPTPLMLPH RSNADVKIGG YDIPKGSNVH VNVWAVARDP AVWKNPFEFR PERFLEEDVD 

       430        440        450        460        470        480 
MKGHDFRLLP FGAGRRVCPG AQLGINLVTS MMSHLLHHFV WTPPQGTKPE EIDMSENPGL 

       490        500 
VTYMRTPVQA VATPRLPSDL YKRVPYDM 

« Hide

References

« Hide 'large scale' references
[1]"Sequence and analysis of chromosome 2 of the plant Arabidopsis thaliana."
Lin X., Kaul S., Rounsley S.D., Shea T.P., Benito M.-I., Town C.D., Fujii C.Y., Mason T.M., Bowman C.L., Barnstead M.E., Feldblyum T.V., Buell C.R., Ketchum K.A., Lee J.J., Ronning C.M., Koo H.L., Moffat K.S., Cronin L.A. expand/collapse author list , Shen M., Pai G., Van Aken S., Umayam L., Tallon L.J., Gill J.E., Adams M.D., Carrera A.J., Creasy T.H., Goodman H.M., Somerville C.R., Copenhaver G.P., Preuss D., Nierman W.C., White O., Eisen J.A., Salzberg S.L., Fraser C.M., Venter J.C.
Nature 402:761-768(1999) [PubMed] [Europe PMC] [Abstract]
Cited for: NUCLEOTIDE SEQUENCE [LARGE SCALE GENOMIC DNA].
Strain: cv. Columbia.
[2]The Arabidopsis Information Resource (TAIR)
Submitted (APR-2011) to the EMBL/GenBank/DDBJ databases
Cited for: GENOME REANNOTATION.
Strain: cv. Columbia.
[3]"Empirical analysis of transcriptional activity in the Arabidopsis genome."
Yamada K., Lim J., Dale J.M., Chen H., Shinn P., Palm C.J., Southwick A.M., Wu H.C., Kim C.J., Nguyen M., Pham P.K., Cheuk R.F., Karlin-Newmann G., Liu S.X., Lam B., Sakano H., Wu T., Yu G. expand/collapse author list , Miranda M., Quach H.L., Tripp M., Chang C.H., Lee J.M., Toriumi M.J., Chan M.M., Tang C.C., Onodera C.S., Deng J.M., Akiyama K., Ansari Y., Arakawa T., Banh J., Banno F., Bowser L., Brooks S.Y., Carninci P., Chao Q., Choy N., Enju A., Goldsmith A.D., Gurjal M., Hansen N.F., Hayashizaki Y., Johnson-Hopson C., Hsuan V.W., Iida K., Karnes M., Khan S., Koesema E., Ishida J., Jiang P.X., Jones T., Kawai J., Kamiya A., Meyers C., Nakajima M., Narusaka M., Seki M., Sakurai T., Satou M., Tamse R., Vaysberg M., Wallender E.K., Wong C., Yamamura Y., Yuan S., Shinozaki K., Davis R.W., Theologis A., Ecker J.R.
Science 302:842-846(2003) [PubMed] [Europe PMC] [Abstract]
Cited for: NUCLEOTIDE SEQUENCE [LARGE SCALE MRNA] OF 79-508.
Strain: cv. Columbia.
[4]"Large-scale analysis of RIKEN Arabidopsis full-length (RAFL) cDNAs."
Totoki Y., Seki M., Ishida J., Nakajima M., Enju A., Kamiya A., Narusaka M., Shin-i T., Nakagawa M., Sakamoto N., Oishi K., Kohara Y., Kobayashi M., Toyoda A., Sakaki Y., Sakurai T., Iida K., Akiyama K. expand/collapse author list , Satou M., Toyoda T., Konagaya A., Carninci P., Kawai J., Hayashizaki Y., Shinozaki K.
Submitted (JUL-2006) to the EMBL/GenBank/DDBJ databases
Cited for: NUCLEOTIDE SEQUENCE [LARGE SCALE MRNA].
Strain: cv. Columbia.
[5]"CYP98A3 from Arabidopsis thaliana is a 3'-hydroxylase of phenolic esters, a missing link in the phenylpropanoid pathway."
Schoch G., Goepfert S., Morant M., Hehn A., Meyer D., Ullmann P., Werck-Reichhart D.
J. Biol. Chem. 276:36566-36574(2001) [PubMed] [Europe PMC] [Abstract]
Cited for: FUNCTION, CATALYTIC ACTIVITY, SUBSTRATE SPECIFICITY, BIOPHYSICOCHEMICAL PROPERTIES, TISSUE SPECIFICITY, INDUCTION BY WOUNDING.
Strain: cv. Columbia.
[6]"The Arabidopsis REF8 gene encodes the 3-hydroxylase of phenylpropanoid metabolism."
Franke R., Humphreys J.M., Hemm M.R., Denault J.W., Ruegger M.O., Cusumano J.C., Chapple C.
Plant J. 30:33-45(2002) [PubMed] [Europe PMC] [Abstract]
Cited for: FUNCTION, MUTAGENESIS OF GLY-444, TISSUE SPECIFICITY, CATALYTIC ACTIVITY, SUBSTRATE SPECIFICITY.
[7]"Changes in secondary metabolism and deposition of an unusual lignin in the ref8 mutant of Arabidopsis."
Franke R., Hemm M.R., Denault J.W., Ruegger M.O., Humphreys J.M., Chapple C.
Plant J. 30:47-59(2002) [PubMed] [Europe PMC] [Abstract]
Cited for: FUNCTION, DISRUPTION PHENOTYPE.
Strain: cv. Columbia.
[8]"Accumulation of coumarins in Arabidopsis thaliana."
Kai K., Shimizu B., Mizutani M., Watanabe K., Sakata K.
Phytochemistry 67:379-386(2006) [PubMed] [Europe PMC] [Abstract]
Cited for: FUNCTION, DISRUPTION PHENOTYPE.
Strain: cv. Columbia.
[9]"A coumaroyl-ester-3-hydroxylase insertion mutant reveals the existence of nonredundant meta-hydroxylation pathways and essential roles for phenolic precursors in cell expansion and plant growth."
Abdulrazzak N., Pollet B., Ehlting J., Larsen K., Asnaghi C., Ronseau S., Proux C., Erhardt M., Seltzer V., Renou J.P., Ullmann P., Pauly M., Lapierre C., Werck-Reichhart D.
Plant Physiol. 140:30-48(2006) [PubMed] [Europe PMC] [Abstract]
Cited for: FUNCTION, DISRUPTION PHENOTYPE.
[10]"Multidimensional protein identification technology (MudPIT) analysis of ubiquitinated proteins in plants."
Maor R., Jones A., Nuehse T.S., Studholme D.J., Peck S.C., Shirasu K.
Mol. Cell. Proteomics 6:601-610(2007) [PubMed] [Europe PMC] [Abstract]
Cited for: UBIQUITINATION [LARGE SCALE ANALYSIS] AT LYS-172 AND LYS-189.
Strain: cv. Landsberg erecta.
[11]"Evolution of a novel phenolic pathway for pollen development."
Matsuno M., Compagnon V., Schoch G.A., Schmitt M., Debayle D., Bassard J.E., Pollet B., Hehn A., Heintz D., Ullmann P., Lapierre C., Bernier F., Ehlting J., Werck-Reichhart D.
Science 325:1688-1692(2009) [PubMed] [Europe PMC] [Abstract]
Cited for: CATALYTIC ACTIVITY, TISSUE SPECIFICITY, 3D-STRUCTURE MODELING.
[12]"Gene engineering, purification, crystallization and preliminary X-ray diffraction of cytochrome P450 p-coumarate-3-hydroxylase (C3H), the Arabidopsis membrane protein."
Kim Y.H., Kwon T., Yang H.J., Kim W., Youn H., Lee J.Y., Youn B.
Protein Expr. Purif. 79:149-155(2011) [PubMed] [Europe PMC] [Abstract]
Cited for: CRYSTALLIZATION.
+Additional computationally mapped references.

Cross-references

Sequence databases

EMBL
GenBank
DDBJ
AC002409 Genomic DNA. Translation: AAB86449.2. Different initiation.
CP002685 Genomic DNA. Translation: AEC09893.1.
AY056105 mRNA. Translation: AAL06992.1.
AK226377 mRNA. Translation: BAE98524.1.
PIRT00753.
RefSeqNP_850337.1. NM_180006.2.
UniGeneAt.19895.
At.24415.

3D structure databases

ProteinModelPortalO22203.
SMRO22203. Positions 47-496.
ModBaseSearch...
MobiDBSearch...

Protein-protein interaction databases

BioGrid4023. 1 interaction.
STRING3702.AT2G40890.1-P.

Proteomic databases

PaxDbO22203.
PRIDEO22203.

Protocols and materials databases

StructuralBiologyKnowledgebaseSearch...

Genome annotation databases

EnsemblPlantsAT2G40890.1; AT2G40890.1; AT2G40890.
GeneID818686.
KEGGath:AT2G40890.

Organism-specific databases

GeneFarm1309. 94.
TAIRAT2G40890.

Phylogenomic databases

eggNOGCOG2124.
HOGENOMHOG000218628.
InParanoidO22203.
KOK09754.
OMANVHVNVW.
PhylomeDBO22203.
ProtClustDBCLSN2682257.

Enzyme and pathway databases

BioCycMetaCyc:AT2G40890-MONOMER.
SABIO-RKO22203.

Gene expression databases

GenevestigatorO22203.

Family and domain databases

Gene3D1.10.630.10. 1 hit.
InterProIPR001128. Cyt_P450.
IPR017972. Cyt_P450_CS.
IPR002401. Cyt_P450_E_grp-I.
[Graphical view]
PfamPF00067. p450. 1 hit.
[Graphical view]
PRINTSPR00463. EP450I.
PR00385. P450.
SUPFAMSSF48264. SSF48264. 1 hit.
PROSITEPS00086. CYTOCHROME_P450. 1 hit.
[Graphical view]
ProtoNetSearch...

Entry information

Entry nameC98A3_ARATH
AccessionPrimary (citable) accession number: O22203
Secondary accession number(s): Q0WWH4, Q940C7
Entry history
Integrated into UniProtKB/Swiss-Prot: December 15, 1998
Last sequence update: January 1, 1998
Last modified: April 16, 2014
This is version 118 of the entry and version 1 of the sequence. [Complete history]
Entry statusReviewed (UniProtKB/Swiss-Prot)
Annotation programPlant Protein Annotation Program

Relevant documents

SIMILARITY comments

Index of protein domains and families

Arabidopsis thaliana

Arabidopsis thaliana: entries and gene names