CHRYS_TANCI
ID CHRYS_TANCI Reviewed; 393 AA.
AC P0C565; L7RFF8;
DT 10-JUL-2007, integrated into UniProtKB/Swiss-Prot.
DT 18-SEP-2019, sequence version 2.
DT 03-AUG-2022, entry version 47.
DE RecName: Full=Bifunctional chrysanthemol synthase, chloroplastic {ECO:0000303|PubMed:25378387};
DE AltName: Full=Chrysanthemol synthase, chloroplastic {ECO:0000303|PubMed:25378387};
DE EC=3.7.1.- {ECO:0000269|PubMed:25378387};
DE AltName: Full=Chrysanthemyl diphosphate synthase, chloroplastic {ECO:0000303|PubMed:11287653};
DE Short=CPPase {ECO:0000303|PubMed:11287653};
DE Short=TcCDS {ECO:0000303|PubMed:25378387};
DE EC=2.5.1.67 {ECO:0000269|PubMed:11287653, ECO:0000269|PubMed:25378387};
DE Flags: Precursor;
GN Name=CDS {ECO:0000303|PubMed:25378387};
OS Tanacetum cinerariifolium (Dalmatian daisy) (Chrysanthemum
OS cinerariifolium).
OC Eukaryota; Viridiplantae; Streptophyta; Embryophyta; Tracheophyta;
OC Spermatophyta; Magnoliopsida; eudicotyledons; Gunneridae; Pentapetalae;
OC asterids; campanulids; Asterales; Asteraceae; Asteroideae; Anthemideae;
OC Anthemidinae; Tanacetum.
OX NCBI_TaxID=118510;
RN [1]
RP NUCLEOTIDE SEQUENCE [MRNA], PARTIAL PROTEIN SEQUENCE, FUNCTION, CATALYTIC
RP ACTIVITY, BIOPHYSICOCHEMICAL PROPERTIES, AND COFACTOR.
RX PubMed=11287653; DOI=10.1073/pnas.071543598;
RA Rivera S.B., Swedlund B.D., King G.J., Bell R.N., Hussey C.E. Jr.,
RA Shattuck-Eidens D.M., Wrobel W.M., Peiser G.D., Poulter C.D.;
RT "Chrysanthemyl diphosphate synthase: isolation of the gene and
RT characterization of the recombinant non-head-to-tail monoterpene synthase
RT from Chrysanthemum cinerariaefolium.";
RL Proc. Natl. Acad. Sci. U.S.A. 98:4373-4378(2001).
RN [2]
RP NUCLEOTIDE SEQUENCE [GENOMIC DNA / MRNA], TISSUE SPECIFICITY, AND
RP DEVELOPMENTAL STAGE.
RC TISSUE=Ovary;
RX PubMed=23104830; DOI=10.1105/tpc.112.105031;
RA Ramirez A.M., Stoopen G., Menzel T.R., Gols R., Bouwmeester H.J., Dicke M.,
RA Jongsma M.A.;
RT "Bidirectional secretions from glandular trichomes of pyrethrum enable
RT immunization of seedlings.";
RL Plant Cell 24:4252-4265(2012).
RN [3]
RP REVIEW.
RX PubMed=15964038; DOI=10.1016/j.phytochem.2005.05.005;
RA Matsuda K., Kikuta Y., Haba A., Nakayama K., Katsuda Y., Hatanaka A.,
RA Komai K.;
RT "Biosynthesis of pyrethrin I in seedlings of Chrysanthemum
RT cinerariaefolium.";
RL Phytochemistry 66:1529-1535(2005).
RN [4]
RP FUNCTION, MUTAGENESIS OF ASN-283, CATALYTIC ACTIVITY, BIOPHYSICOCHEMICAL
RP PROPERTIES, PATHWAY, AND SUBCELLULAR LOCATION.
RX PubMed=25378387; DOI=10.1074/jbc.m114.623348;
RA Yang T., Gao L., Hu H., Stoopen G., Wang C., Jongsma M.A.;
RT "Chrysanthemyl diphosphate synthase operates in planta as a bifunctional
RT enzyme with chrysanthemol synthase activity.";
RL J. Biol. Chem. 289:36325-36335(2014).
RN [5]
RP TISSUE SPECIFICITY.
RX PubMed=29122986; DOI=10.1104/pp.17.01330;
RA Xu H., Moghe G.D., Wiegert-Rininger K., Schilmiller A.L., Barry C.S.,
RA Last R.L., Pichersky E.;
RT "Coexpression analysis identifies two oxidoreductases involved in the
RT biosynthesis of the monoterpene acid moiety of natural pyrethrin
RT insecticides in Tanacetum cinerariifolium.";
RL Plant Physiol. 176:524-537(2018).
RN [6]
RP REVIEW.
RX PubMed=30468448; DOI=10.1039/c8np00077h;
RA Liu Y., Jing S.-X., Luo S.-H., Li S.-H.;
RT "Non-volatile natural products in plant glandular trichomes: chemistry,
RT biological activities and biosynthesis.";
RL Nat. Prod. Rep. 36:626-665(2019).
CC -!- FUNCTION: Component of the monoterpenoid pyrethrins biosynthesis;
CC pyrethrins are widely used plant-derived pesticide (PubMed:30468448).
CC Catalyzes the condensation of two molecules of dimethylallyl
CC diphosphate to produce chrysanthemyl diphosphate (CPP), a monoterpene
CC with a non-head-to-tail or irregular c1'-2-3 linkage between isoprenoid
CC units (PubMed:11287653, PubMed:25378387). In a second step, hydrolyzes
CC the diphosphate moiety of CPP to form chrysanthemol (PubMed:25378387).
CC With a lower efficiency, can also converts dimethylallyl diphosphate
CC into lavandulyl diphosphate (LPP), and subsequently LPP into lavandulol
CC (PubMed:25378387). {ECO:0000269|PubMed:11287653,
CC ECO:0000269|PubMed:25378387, ECO:0000303|PubMed:30468448}.
CC -!- CATALYTIC ACTIVITY:
CC Reaction=2 dimethylallyl diphosphate = (R,R)-chrysanthemyl diphosphate
CC + diphosphate; Xref=Rhea:RHEA:14009, ChEBI:CHEBI:33019,
CC ChEBI:CHEBI:57623, ChEBI:CHEBI:58819; EC=2.5.1.67;
CC Evidence={ECO:0000269|PubMed:11287653, ECO:0000269|PubMed:25378387};
CC PhysiologicalDirection=left-to-right; Xref=Rhea:RHEA:14010;
CC Evidence={ECO:0000269|PubMed:11287653, ECO:0000269|PubMed:25378387};
CC -!- CATALYTIC ACTIVITY:
CC Reaction=(R,R)-chrysanthemyl diphosphate + H2O = (R,R)-chrysanthemol +
CC diphosphate; Xref=Rhea:RHEA:60024, ChEBI:CHEBI:15377,
CC ChEBI:CHEBI:33019, ChEBI:CHEBI:58819, ChEBI:CHEBI:143898;
CC Evidence={ECO:0000269|PubMed:25378387};
CC PhysiologicalDirection=left-to-right; Xref=Rhea:RHEA:60025;
CC Evidence={ECO:0000269|PubMed:25378387};
CC -!- CATALYTIC ACTIVITY:
CC Reaction=(R)-lavandulyl diphosphate + H2O = (R)-lavandulol +
CC diphosphate; Xref=Rhea:RHEA:60696, ChEBI:CHEBI:15377,
CC ChEBI:CHEBI:33019, ChEBI:CHEBI:50283, ChEBI:CHEBI:143949;
CC Evidence={ECO:0000269|PubMed:25378387};
CC PhysiologicalDirection=left-to-right; Xref=Rhea:RHEA:60697;
CC Evidence={ECO:0000269|PubMed:25378387};
CC -!- COFACTOR:
CC Name=Mg(2+); Xref=ChEBI:CHEBI:18420;
CC Evidence={ECO:0000269|PubMed:11287653};
CC Note=Binds 2 Mg(2+) ions per subunit. {ECO:0000269|PubMed:11287653};
CC -!- BIOPHYSICOCHEMICAL PROPERTIES:
CC Kinetic parameters:
CC KM=600 uM for dimethylallyl diphosphate
CC {ECO:0000269|PubMed:11287653};
CC KM=196 uM for chrysanthemyl diphosphate
CC {ECO:0000269|PubMed:25378387};
CC Note=kcat is 0.5 min(-1) with dimethylallyl diphosphate as substrate
CC (PubMed:11287653). kcat is 0.0033 min(-1) with chrysanthemyl
CC diphosphate as substrate (PubMed:25378387).
CC {ECO:0000269|PubMed:11287653, ECO:0000269|PubMed:25378387};
CC pH dependence:
CC Optimum pH is 6.5-8. {ECO:0000269|PubMed:11287653};
CC -!- PATHWAY: Isoprenoid biosynthesis. {ECO:0000269|PubMed:25378387}.
CC -!- SUBCELLULAR LOCATION: Plastid, chloroplast
CC {ECO:0000269|PubMed:25378387}.
CC -!- TISSUE SPECIFICITY: Restricted to glandular trichomes during achene
CC maturation (PubMed:23104830). Expressed in flowers and in both ray and
CC disk florets (PubMed:29122986). {ECO:0000269|PubMed:23104830,
CC ECO:0000269|PubMed:29122986}.
CC -!- DEVELOPMENTAL STAGE: Mostly expressed in ovaries of flowers at stages
CC S1 to S7 (bud to overblown), before the first disk florets opening, and
CC prior embryos formation. {ECO:0000269|PubMed:23104830}.
CC -!- SIMILARITY: Belongs to the FPP/GGPP synthase family. {ECO:0000305}.
CC ---------------------------------------------------------------------------
CC Copyrighted by the UniProt Consortium, see https://www.uniprot.org/terms
CC Distributed under the Creative Commons Attribution (CC BY 4.0) License
CC ---------------------------------------------------------------------------
DR EMBL; I13995; -; NOT_ANNOTATED_CDS; Unassigned_DNA.
DR EMBL; JX913537; AFZ61535.1; -; Genomic_DNA.
DR EMBL; JX913536; AGC03154.1; -; mRNA.
DR AlphaFoldDB; P0C565; -.
DR SMR; P0C565; -.
DR BRENDA; 2.5.1.67; 8608.
DR GO; GO:0009507; C:chloroplast; IDA:UniProtKB.
DR GO; GO:0033849; F:chrysanthemyl diphosphate synthase activity; IDA:UniProtKB.
DR GO; GO:0016787; F:hydrolase activity; IEA:UniProtKB-KW.
DR GO; GO:0000287; F:magnesium ion binding; IDA:UniProtKB.
DR GO; GO:0008299; P:isoprenoid biosynthetic process; IDA:UniProtKB.
DR CDD; cd00685; Trans_IPPS_HT; 1.
DR Gene3D; 1.10.600.10; -; 1.
DR InterPro; IPR039702; FPS1-like.
DR InterPro; IPR008949; Isoprenoid_synthase_dom_sf.
DR InterPro; IPR000092; Polyprenyl_synt.
DR InterPro; IPR033749; Polyprenyl_synt_CS.
DR PANTHER; PTHR11525; PTHR11525; 1.
DR Pfam; PF00348; polyprenyl_synt; 1.
DR SUPFAM; SSF48576; SSF48576; 1.
DR PROSITE; PS00723; POLYPRENYL_SYNTHASE_1; 1.
PE 1: Evidence at protein level;
KW Chloroplast; Direct protein sequencing; Hydrolase; Isoprene biosynthesis;
KW Magnesium; Metal-binding; Plastid; Transferase; Transit peptide.
FT TRANSIT 1..53
FT /note="Chloroplast"
FT /evidence="ECO:0000255"
FT CHAIN 54..393
FT /note="Bifunctional chrysanthemol synthase, chloroplastic"
FT /id="PRO_0000293960"
FT REGION 1..22
FT /note="Disordered"
FT /evidence="ECO:0000256|SAM:MobiDB-lite"
FT BINDING 99
FT /ligand="dimethylallyl diphosphate"
FT /ligand_id="ChEBI:CHEBI:57623"
FT /ligand_label="1"
FT /evidence="ECO:0000250|UniProtKB:P14324"
FT BINDING 102
FT /ligand="dimethylallyl diphosphate"
FT /ligand_id="ChEBI:CHEBI:57623"
FT /ligand_label="1"
FT /evidence="ECO:0000250|UniProtKB:P14324"
FT BINDING 137
FT /ligand="dimethylallyl diphosphate"
FT /ligand_id="ChEBI:CHEBI:57623"
FT /ligand_label="1"
FT /evidence="ECO:0000250|UniProtKB:P14324"
FT BINDING 144
FT /ligand="Mg(2+)"
FT /ligand_id="ChEBI:CHEBI:18420"
FT /ligand_label="1"
FT /evidence="ECO:0000250|UniProtKB:P14324"
FT BINDING 144
FT /ligand="Mg(2+)"
FT /ligand_id="ChEBI:CHEBI:18420"
FT /ligand_label="2"
FT /evidence="ECO:0000250|UniProtKB:P14324"
FT BINDING 148
FT /ligand="Mg(2+)"
FT /ligand_id="ChEBI:CHEBI:18420"
FT /ligand_label="1"
FT /evidence="ECO:0000250|UniProtKB:P14324"
FT BINDING 148
FT /ligand="Mg(2+)"
FT /ligand_id="ChEBI:CHEBI:18420"
FT /ligand_label="2"
FT /evidence="ECO:0000250|UniProtKB:P14324"
FT BINDING 153
FT /ligand="dimethylallyl diphosphate"
FT /ligand_id="ChEBI:CHEBI:57623"
FT /ligand_label="2"
FT /evidence="ECO:0000250|UniProtKB:Q12051"
FT BINDING 154
FT /ligand="dimethylallyl diphosphate"
FT /ligand_id="ChEBI:CHEBI:57623"
FT /ligand_label="1"
FT /evidence="ECO:0000250|UniProtKB:P14324"
FT BINDING 241
FT /ligand="dimethylallyl diphosphate"
FT /ligand_id="ChEBI:CHEBI:57623"
FT /ligand_label="2"
FT /evidence="ECO:0000250|UniProtKB:Q12051"
FT BINDING 280
FT /ligand="dimethylallyl diphosphate"
FT /ligand_id="ChEBI:CHEBI:57623"
FT /ligand_label="2"
FT /evidence="ECO:0000250|UniProtKB:Q12051"
FT BINDING 287
FT /ligand="dimethylallyl diphosphate"
FT /ligand_id="ChEBI:CHEBI:57623"
FT /ligand_label="2"
FT /evidence="ECO:0000250|UniProtKB:Q12051"
FT BINDING 297
FT /ligand="dimethylallyl diphosphate"
FT /ligand_id="ChEBI:CHEBI:57623"
FT /ligand_label="1"
FT /evidence="ECO:0000250|UniProtKB:Q12051"
FT BINDING 306
FT /ligand="dimethylallyl diphosphate"
FT /ligand_id="ChEBI:CHEBI:57623"
FT /ligand_label="2"
FT /evidence="ECO:0000250|UniProtKB:Q12051"
FT SITE 283
FT /note="Required for catalytic activities"
FT /evidence="ECO:0000269|PubMed:25378387"
FT MUTAGEN 283
FT /note="N->D,G: Abolished terpene synthase and
FT prenyltransferase activities leading to lost production of
FT chrysanthemyl diphosphate and chrysanthemol."
FT /evidence="ECO:0000269|PubMed:25378387"
FT CONFLICT 2..5
FT /note="ACSS -> SWCLLC (in Ref. 1; I13995)"
FT /evidence="ECO:0000305"
SQ SEQUENCE 393 AA; 44995 MW; EB5744A881B4EEB1 CRC64;
MACSSSLSSK WASWGASSRP HPSVQPFVTR KNVVRYHKPT SELSYSPLTT TLSSNLDSQF
MQVYETLKSE LIHDPSFEFD DDSRQWVERM IDYNVPGGKM VRGYSVVDSY QLLKGEELTE
DEAFLACALG WCTEWLQAFI LVLDDIMDGS HTRRGQPCWF RLPEVGVVAI NDGVLLRNHV
HRILKKYFQG KPYYVHLLDL FNETEFQTIS GQMIDTICRL AGQKDLSKYT MTLNRRIVQY
KGSYYSCYLP IACALLMFGE NLEDHVQVKD ILVELGMYYQ IQNDYLDTFG DPDVFGKTGT
DIEECKCSWL IAKALELANE EQKKILSENY GINDPSKVAK VKELYHALDL KGAYEDYETN
LYETSMTSIK AHPNIAVQAV LKSCLEKMYK GHK
