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LOLE2_EPIUN
ID   LOLE2_EPIUN             Reviewed;         256 AA.
AC   Q5MNH2;
DT   23-MAY-2018, integrated into UniProtKB/Swiss-Prot.
DT   01-FEB-2005, sequence version 1.
DT   03-AUG-2022, entry version 32.
DE   RecName: Full=Dioxygenase lolE2 {ECO:0000303|PubMed:15654104};
DE            EC=1.14.11.- {ECO:0000305|PubMed:15654104};
DE   AltName: Full=Loline biosynthesis cluster 2 protein E {ECO:0000303|PubMed:15654104};
GN   Name=lolE2 {ECO:0000303|PubMed:15654104};
GN   Synonyms=lolE {ECO:0000303|PubMed:15654104};
OS   Epichloe uncinata (Endophyte fungus) (Neotyphodium uncinatum).
OC   Eukaryota; Fungi; Dikarya; Ascomycota; Pezizomycotina; Sordariomycetes;
OC   Hypocreomycetidae; Hypocreales; Clavicipitaceae; Epichloe.
OX   NCBI_TaxID=5050;
RN   [1]
RP   NUCLEOTIDE SEQUENCE [GENOMIC DNA], INDUCTION, AND FUNCTION.
RC   STRAIN=CBS 102646;
RX   PubMed=15654104; DOI=10.1534/genetics.104.035972;
RA   Spiering M.J., Moon C.D., Wilkinson H.H., Schardl C.L.;
RT   "Gene clusters for insecticidal loline alkaloids in the grass-endophytic
RT   fungus Neotyphodium uncinatum.";
RL   Genetics 169:1403-1414(2005).
RN   [2]
RP   FUNCTION.
RX   PubMed=15861432; DOI=10.1002/cbic.200400327;
RA   Blankenship J.D., Houseknecht J.B., Pal S., Bush L.P., Grossman R.B.,
RA   Schardl C.L.;
RT   "Biosynthetic precursors of fungal pyrrolizidines, the loline alkaloids.";
RL   ChemBioChem 6:1016-1022(2005).
RN   [3]
RP   FUNCTION.
RX   PubMed=16755627; DOI=10.1002/cbic.200600066;
RA   Faulkner J.R., Hussaini S.R., Blankenship J.D., Pal S., Branan B.M.,
RA   Grossman R.B., Schardl C.L.;
RT   "On the sequence of bond formation in loline alkaloid biosynthesis.";
RL   ChemBioChem 7:1078-1088(2006).
RN   [4]
RP   FUNCTION.
RC   STRAIN=CBS 102646;
RX   PubMed=18655839; DOI=10.1016/j.fgb.2008.07.001;
RA   Spiering M.J., Faulkner J.R., Zhang D.X., Machado C., Grossman R.B.,
RA   Schardl C.L.;
RT   "Role of the LolP cytochrome P450 monooxygenase in loline alkaloid
RT   biosynthesis.";
RL   Fungal Genet. Biol. 45:1307-1314(2008).
RN   [5]
RP   FUNCTION.
RX   PubMed=24374065; DOI=10.1016/j.phytochem.2013.11.015;
RA   Pan J., Bhardwaj M., Faulkner J.R., Nagabhyru P., Charlton N.D.,
RA   Higashi R.M., Miller A.F., Young C.A., Grossman R.B., Schardl C.L.;
RT   "Ether bridge formation in loline alkaloid biosynthesis.";
RL   Phytochemistry 98:60-68(2014).
RN   [6]
RP   FUNCTION, AND BIOTECHNOLOGY.
RX   PubMed=25531527; DOI=10.1371/journal.pone.0115590;
RA   Pan J., Bhardwaj M., Nagabhyru P., Grossman R.B., Schardl C.L.;
RT   "Enzymes from fungal and plant origin required for chemical diversification
RT   of insecticidal loline alkaloids in grass-Epichloe symbiota.";
RL   PLoS ONE 9:E115590-E115590(2014).
RN   [7]
RP   FUNCTION.
RX   PubMed=29537853; DOI=10.1021/acs.biochem.8b00157;
RA   Pan J., Bhardwaj M., Zhang B., Chang W.C., Schardl C.L., Krebs C.,
RA   Grossman R.B., Bollinger J.M. Jr.;
RT   "Installation of the ether bridge of lolines by the iron- and 2-
RT   oxoglutarate-dependent oxygenase, lolO: regio- and stereochemistry of
RT   sequential hydroxylation and oxacyclization reactions.";
RL   Biochemistry 57:2074-2083(2018).
CC   -!- FUNCTION: Dioxygenase; part of the gene cluster that mediates the
CC       biosynthesis of loline alkaloids, potent insecticidal agents composed
CC       of a pyrrolizidine ring system and an uncommon ether bridge linking
CC       carbons 2 and 7 (PubMed:15654104). Lolines are structurally
CC       differentiated by the various modifications of the L-amino group and
CC       include norloline, loline, N-methylloline, N-acetylloline, N-
CC       acetylnorloline, and N-formylloline (PubMed:15861432, PubMed:25531527).
CC       The first committed step is the condensation of O-acetyl-L-homoserine
CC       (derived from L-aspartic acid) and L-proline, probably catalyzed by the
CC       gamma-type pyridoxal 5'-phosphate(PLP)-dependent enzyme lolC, to give
CC       the diamino diacid, NACPP (PubMed:15861432, PubMed:16755627). Ensuing
CC       cyclization, decarboxylation, and acetylation steps yield 1-exo-
CC       acetamidopyrrolizidine (AcAP)(PubMed:24374065). LolO is required for
CC       installation of the ether bridge upon the pathway intermediate, 1-exo-
CC       acetamidopyrrolizidine (AcAP) (PubMed:29537853). In sequential 2-
CC       oxoglutarate- and O(2)-consuming steps, lolO removes hydrogens from C2
CC       and C7 of AcAP to form both carbon-oxygen bonds in N-acetylnorloline
CC       (NANL), the precursor to all other lolines (PubMed:24374065,
CC       PubMed:29537853). The enzymes lolD, lolE, lolF and lolT have also been
CC       proposed to be involved in the ether-bridge installation
CC       (PubMed:15654104). Further processing of the exocyclic moiety of NANL
CC       by fungal N-acetamidase (LolN), methyltransferase (LolM), and
CC       cytochrome P450 (LolP) enzymes, with occasional involvement of a plant
CC       acetyltransferase, generates the other known lolines (PubMed:25531527,
CC       PubMed:18655839). LolN transforms NANL to norlonine which is
CC       monomethylated and dimethylated to respectively lonine and N-
CC       methyllonine (NML) by lolM (PubMed:25531527). LolP catalyzes
CC       hydroxylation of the methyl group in N-methylloline (NML) and further
CC       oxygenation to N-formylloline (NFL) (PubMed:18655839). A plant
CC       acetyltransferase is responsible for the acetylation of loline to form
CC       N-acetylloline (NAL) (PubMed:25531527). LolA might interact with
CC       aspartate kinase to prevent feedback inhibition of its activity by
CC       these end products and thereby promote production of L-homoserine from
CC       L-aspartate (PubMed:15654104). {ECO:0000269|PubMed:15654104,
CC       ECO:0000269|PubMed:15861432, ECO:0000269|PubMed:16755627,
CC       ECO:0000269|PubMed:18655839, ECO:0000269|PubMed:24374065,
CC       ECO:0000269|PubMed:25531527, ECO:0000269|PubMed:29537853}.
CC   -!- COFACTOR:
CC       Name=Fe cation; Xref=ChEBI:CHEBI:24875;
CC         Evidence={ECO:0000250|UniProtKB:G8GV69};
CC   -!- PATHWAY: Alkaloid biosynthesis. {ECO:0000305|PubMed:15654104}.
CC   -!- SUBUNIT: Homodimer. {ECO:0000250|UniProtKB:Q4WAW9}.
CC   -!- INDUCTION: Expression is induced in loline alkaloid-producing cultures
CC       as well as in planta (PubMed:15654104). {ECO:0000269|PubMed:15654104}.
CC   -!- BIOTECHNOLOGY: Loline alkaloids show broad-spectrum anti-insect
CC       activity, and different lolines may have different biological
CC       activities (PubMed:25531527). In vitro tests of NFL, NAL, NML, and
CC       semisynthetic loline derivatives with long carbon-chain acylations on
CC       the 1-amine have shown that many are effective against both fall
CC       armyworm larvae and European corn borer larvae, but the effects seem to
CC       differ depending on the modifications (PubMed:25531527). N-Formylloline
CC       reduces the weight gain of fall armyworms by deterring feeding, and
CC       does not significantly affect corn borers (PubMed:25531527). In
CC       contrast, NAL reduces the weight gain of corn borer larvae without
CC       changing larval feeding behavior, indicating that its effect is due to
CC       metabolic toxicity. N-formylloline, NAL, and NML are almost as potent
CC       as nicotine in insecticidal activity against green bugs
CC       (PubMed:25531527). {ECO:0000305|PubMed:25531527}.
CC   -!- SIMILARITY: Belongs to the PhyH family. {ECO:0000305}.
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DR   EMBL; AY723750; AAV68701.1; -; Genomic_DNA.
DR   AlphaFoldDB; Q5MNH2; -.
DR   SMR; Q5MNH2; -.
DR   GO; GO:0051213; F:dioxygenase activity; IEA:UniProtKB-KW.
DR   GO; GO:0046872; F:metal ion binding; IEA:UniProtKB-KW.
DR   GO; GO:0009820; P:alkaloid metabolic process; IEA:UniProtKB-KW.
DR   InterPro; IPR008775; Phytyl_CoA_dOase.
DR   Pfam; PF05721; PhyH; 1.
PE   2: Evidence at transcript level;
KW   Alkaloid metabolism; Dioxygenase; Iron; Metal-binding; Oxidoreductase.
FT   CHAIN           1..256
FT                   /note="Dioxygenase lolE2"
FT                   /id="PRO_0000444350"
FT   BINDING         125
FT                   /ligand="Fe cation"
FT                   /ligand_id="ChEBI:CHEBI:24875"
FT                   /evidence="ECO:0000250|UniProtKB:G8GV69"
FT   BINDING         127
FT                   /ligand="Fe cation"
FT                   /ligand_id="ChEBI:CHEBI:24875"
FT                   /evidence="ECO:0000250|UniProtKB:G8GV69"
FT   BINDING         203
FT                   /ligand="Fe cation"
FT                   /ligand_id="ChEBI:CHEBI:24875"
FT                   /evidence="ECO:0000250|UniProtKB:G8GV69"
SQ   SEQUENCE   256 AA;  28636 MW;  A57D97186D757A02 CRC64;
     MTAASSPHPG VSAEDIEFYQ ANGYLRLPQE AHGLFDDLAK LQVWVAEISQ WGLETGKWRH
     YYETTNGKHL LWGTEKLMEY HAPMQDLISG EAPLALLKSL TGKDMVVFKD EIGWKLPGGK
     GAVPHLDRPA YSMFAPEFIE IMIAVDAHTV ENGCLQFVPG SHKEAAPISA DGRIASAWLE
     GKEFIPMVLD PGDVLIFNES MAHRLEPNKT DQRRAAVFGT YHFDLSQPDL RDKFYAHRLI
     HSPPENAWVE KVGAQT
 
 
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