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Protein

Chlorophenol O-methyltransferase

Gene

cmt1

Organism
Trichoderma longibrachiatum
Status
Reviewed-Annotation score: -Experimental evidence at protein leveli

Functioni

Chlorophenol O-methyltransferase that methylates chlorophenols into chloroanisoles which are thought to be responsible for cork taint of wines (PubMed:20144725, PubMed:12957890). The only single chlorophenol (CP) methylated is 2-CP; neither 3-CP nor 4-CP are effective substrates (PubMed:12957890). Within the dichlorophenols (DCPs), 2,4-DCP supports the highest rate of O-methylation, and the activity decreases in the following order: 2,3-DCP, 2,5-DCP, 2,6-DCP, and 3,4-DCP (PubMed:12957890). Within the trichlorophenol (TCP) group, the maximal activity is observed with 2,3,4-TCP, whereas there is increasingly reduced activity with 2,4,5-TCP, 2,4,6-TCP, and 2,3,6-TCP (PubMed:12957890). The only tetrachlorophenol (TeCP) that is methylated is 2,3,4,5-TeCP, since no activity can be detected with 2,3,4,6-TeCP and 2,3,5,6-TeCP (PubMed:12957890). Is also able to methylate other halogenated phenols containing fluoro or bromo substituents, whereas other hydroxylated compounds, such as hydroxylated benzoic acids, hydroxybenzaldehydes, phenol, 2-metoxyphenol, and dihydroxybenzene, were not methylated (PubMed:12957890).2 Publications

Catalytic activityi

S-adenosyl-L-methionine + trichlorophenol = S-adenosyl-L-homocysteine + trichloroanisole.1 Publication

Cofactori

S-adenosyl-L-methionine1 Publication

Activity regulationi

S-adenosyl-L-homocysteine acts as a competitive inhibitor (PubMed:12957890). Also strongly inhibited by low concentrations of several metal ions, such as Cu2+, Hg2+, Zn2+, and Ag+, and to a lesser extent by p-chloromercuribenzoic acid, but it is not significantly affected by several thiols or other thiol reagents (PubMed:12957890).1 Publication

Kineticsi

  1. KM=136 µM for 2,4,6-trichlorophenol (2,4,6-TCP)1 Publication
  2. KM=284 µM for S-adenosyl-L-methionine (SAM)1 Publication

    pH dependencei

    Optimum pH is 8.2-8.5.1 Publication

    Temperature dependencei

    Optimum temperature is 28 degrees Celsius.1 Publication

    Sites

    Feature keyPosition(s)DescriptionActionsGraphical viewLength
    Binding sitei320S-adenosyl-L-methioninePROSITE-ProRule annotation1
    Active sitei368Proton acceptorPROSITE-ProRule annotation1

    GO - Molecular functioni

    Keywordsi

    Molecular functionMethyltransferase, Transferase
    LigandS-adenosyl-L-methionine

    Names & Taxonomyi

    Protein namesi
    Recommended name:
    Chlorophenol O-methyltransferase1 Publication (EC:2.1.1.1361 Publication)
    Short name:
    COMPT1 Publication
    Gene namesi
    Name:cmt11 Publication
    OrganismiTrichoderma longibrachiatum
    Taxonomic identifieri5548 [NCBI]
    Taxonomic lineageiEukaryotaFungiDikaryaAscomycotaPezizomycotinaSordariomycetesHypocreomycetidaeHypocrealesHypocreaceaeTrichoderma

    Pathology & Biotechi

    Biotechnological usei

    Chloroanisoles such as 2,4,6-trichloroanisole (TCA) are known compounds which are usually associated with wine faults (PubMed:28842039). They belong to the family of haloanisoles which are key substances responsible for cork taint in wines (PubMed:28842039).1 Publication

    PTM / Processingi

    Molecule processing

    Feature keyPosition(s)DescriptionActionsGraphical viewLength
    ChainiPRO_00004441061 – 467Chlorophenol O-methyltransferaseAdd BLAST467

    Expressioni

    Inductioni

    Expression is specifically induced by several chlorophenols, especially if they contained three or more chlorine atoms in their structures, such as 2,4,6-trichlorophenol (PubMed:20144725, PubMed:12957890).2 Publications

    Structurei

    3D structure databases

    ProteinModelPortaliD3H5H5
    ModBaseiSearch...
    MobiDBiSearch...

    Family & Domainsi

    Sequence similaritiesi

    Family and domain databases

    Gene3Di1.10.10.10, 1 hit
    InterProiView protein in InterPro
    IPR016461 O-MeTrfase_COMT
    IPR001077 O_MeTrfase_2
    IPR029063 SAM-dependent_MTases
    IPR036388 WH-like_DNA-bd_sf
    IPR036390 WH_DNA-bd_sf
    PfamiView protein in Pfam
    PF00891 Methyltransf_2, 1 hit
    SUPFAMiSSF46785 SSF46785, 1 hit
    SSF53335 SSF53335, 1 hit
    PROSITEiView protein in PROSITE
    PS51683 SAM_OMT_II, 1 hit

    Sequencei

    Sequence statusi: Complete.

    D3H5H5-1 [UniParc]FASTAAdd to basket
    « Hide
            10         20         30         40         50
    MAELRAPSSL STERNGSASN TDVDKQKLNH LYQNGNKKTG SAESRMLVLA
    60 70 80 90 100
    ETIRAETQKL HAYLESNGIA QPDLSVDAPD DFPPLPDEIQ ESRQKIFLAS
    110 120 130 140 150
    RELTDIVRGP RETVRYAVWS YLDTLSLQLI NSYGIAKLVP LDAPIKLTEL
    160 170 180 190 200
    QSKTPLEPVH LARALRHAMT NNIFREPSPG YIAHTSSSRI LAQDPALQAW
    210 220 230 240 250
    VGFNSEDAFP AAGHVLQALK DHPEAISSTH AGFNYAFNTV GQEPMFATLG
    260 270 280 290 300
    KDLARAKRFA QAMHSFSHGE GYKVSYFVDN YDLSEVDKRG GTFVDIGGSH
    310 320 330 340 350
    GFVSVELAKR WKDMKFIVED LPKTIESAPQ PISDDKTVAD RISLQAHDFF
    360 370 380 390 400
    QEQPVKGADV YFFRWIIHNH AKPYAVSILR NLIPALKPGA RVVINDYCIR
    410 420 430 440 450
    EAGSENAWDE KLLRNMDMIM GALLNAQERE EWEFRELFEA ADPRFKFKGV
    460
    QRVENCKMSV IEAVWDE
    Length:467
    Mass (Da):52,461
    Last modified:March 23, 2010 - v1
    Checksum:iE23B1F53AA97E414
    GO

    Sequence databases

    Select the link destinations:
    EMBLi
    GenBanki
    DDBJi
    Links Updated
    FN554867 Genomic DNA Translation: CBG37723.1

    Similar proteinsi

    Cross-referencesi

    Sequence databases

    Select the link destinations:
    EMBLi
    GenBanki
    DDBJi
    Links Updated
    FN554867 Genomic DNA Translation: CBG37723.1

    3D structure databases

    ProteinModelPortaliD3H5H5
    ModBaseiSearch...
    MobiDBiSearch...

    Protocols and materials databases

    Structural Biology KnowledgebaseSearch...

    Family and domain databases

    Gene3Di1.10.10.10, 1 hit
    InterProiView protein in InterPro
    IPR016461 O-MeTrfase_COMT
    IPR001077 O_MeTrfase_2
    IPR029063 SAM-dependent_MTases
    IPR036388 WH-like_DNA-bd_sf
    IPR036390 WH_DNA-bd_sf
    PfamiView protein in Pfam
    PF00891 Methyltransf_2, 1 hit
    SUPFAMiSSF46785 SSF46785, 1 hit
    SSF53335 SSF53335, 1 hit
    PROSITEiView protein in PROSITE
    PS51683 SAM_OMT_II, 1 hit
    ProtoNetiSearch...

    Entry informationi

    Entry nameiCMT1_TRILO
    AccessioniPrimary (citable) accession number: D3H5H5
    Entry historyiIntegrated into UniProtKB/Swiss-Prot: May 23, 2018
    Last sequence update: March 23, 2010
    Last modified: September 12, 2018
    This is version 22 of the entry and version 1 of the sequence. See complete history.
    Entry statusiReviewed (UniProtKB/Swiss-Prot)
    Annotation programFungal Protein Annotation Program
    UniProt is an ELIXIR core data resource
    Main funding by: National Institutes of Health

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