Kauniolide synthase is a P450 with unusual hydroxylation and cyclization-elimination activity View Full Text


Ontology type: schema:ScholarlyArticle      Open Access: True


Article Info

DATE

2018-11-07

AUTHORS

Qing Liu, Arman Beyraghdar Kashkooli, David Manzano, Irini Pateraki, Lea Richard, Pim Kolkman, Maria Fátima Lucas, Victor Guallar, Ric C.H. de Vos, Maurice C. R. Franssen, Alexander van der Krol, Harro Bouwmeester

ABSTRACT

Guaianolides are an important class of sesquiterpene lactones with unique biological and pharmaceutical properties. They have been postulated to be derived from germacranolides, but for years no progress has been made in the elucidation of their biosynthesis that requires an unknown cyclization mechanism. Here we demonstrate the isolation and characterization of a cytochrome P450 from feverfew (Tanacetum parthenium), kauniolide synthase. Kauniolide synthase catalyses the formation of the guaianolide kauniolide from the germacranolide substrate costunolide. Unlike most cytochrome P450s, kauniolide synthase combines stereoselective hydroxylation of costunolide at the C3 position, with water elimination, cyclization and regioselective deprotonation. This unique mechanism of action is supported by in silico modelling and docking experiments. The full kauniolide biosynthesis pathway is reconstructed in the heterologous hosts Nicotiana benthamiana and yeast, paving the way for biotechnological production of guaianolide-type sesquiterpene lactones. More... »

PAGES

4657

Identifiers

URI

http://scigraph.springernature.com/pub.10.1038/s41467-018-06565-8

DOI

http://dx.doi.org/10.1038/s41467-018-06565-8

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1107969567

PUBMED

https://www.ncbi.nlm.nih.gov/pubmed/30405138


Indexing Status Check whether this publication has been indexed by Scopus and Web Of Science using the SN Indexing Status Tool
Incoming Citations Browse incoming citations for this publication using opencitations.net

JSON-LD is the canonical representation for SciGraph data.

TIP: You can open this SciGraph record using an external JSON-LD service: JSON-LD Playground Google SDTT

[
  {
    "@context": "https://springernature.github.io/scigraph/jsonld/sgcontext.json", 
    "about": [
      {
        "id": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/06", 
        "inDefinedTermSet": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/", 
        "name": "Biological Sciences", 
        "type": "DefinedTerm"
      }, 
      {
        "id": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/0601", 
        "inDefinedTermSet": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/", 
        "name": "Biochemistry and Cell Biology", 
        "type": "DefinedTerm"
      }, 
      {
        "inDefinedTermSet": "https://www.nlm.nih.gov/mesh/", 
        "name": "Biosynthetic Pathways", 
        "type": "DefinedTerm"
      }, 
      {
        "inDefinedTermSet": "https://www.nlm.nih.gov/mesh/", 
        "name": "Cyclization", 
        "type": "DefinedTerm"
      }, 
      {
        "inDefinedTermSet": "https://www.nlm.nih.gov/mesh/", 
        "name": "Cytochrome P-450 Enzyme System", 
        "type": "DefinedTerm"
      }, 
      {
        "inDefinedTermSet": "https://www.nlm.nih.gov/mesh/", 
        "name": "Hydroxylation", 
        "type": "DefinedTerm"
      }, 
      {
        "inDefinedTermSet": "https://www.nlm.nih.gov/mesh/", 
        "name": "Molecular Docking Simulation", 
        "type": "DefinedTerm"
      }, 
      {
        "inDefinedTermSet": "https://www.nlm.nih.gov/mesh/", 
        "name": "Saccharomyces cerevisiae", 
        "type": "DefinedTerm"
      }, 
      {
        "inDefinedTermSet": "https://www.nlm.nih.gov/mesh/", 
        "name": "Sesquiterpenes", 
        "type": "DefinedTerm"
      }, 
      {
        "inDefinedTermSet": "https://www.nlm.nih.gov/mesh/", 
        "name": "Tanacetum", 
        "type": "DefinedTerm"
      }, 
      {
        "inDefinedTermSet": "https://www.nlm.nih.gov/mesh/", 
        "name": "Tobacco", 
        "type": "DefinedTerm"
      }
    ], 
    "author": [
      {
        "affiliation": {
          "alternateName": "Department of Plant and Environmental Sciences, University of Copenhagen, Thorvaldsensvej 40, 1871, Frederiksberg, Denmark", 
          "id": "http://www.grid.ac/institutes/grid.5254.6", 
          "name": [
            "Laboratory of Plant Physiology, Wageningen University and Research, Droevendaalsesteeg 1, 6708 PB, Wageningen, The Netherlands", 
            "Department of Plant and Environmental Sciences, University of Copenhagen, Thorvaldsensvej 40, 1871, Frederiksberg, Denmark"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Liu", 
        "givenName": "Qing", 
        "id": "sg:person.01341013542.98", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01341013542.98"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Laboratory of Plant Physiology, Wageningen University and Research, Droevendaalsesteeg 1, 6708 PB, Wageningen, The Netherlands", 
          "id": "http://www.grid.ac/institutes/grid.4818.5", 
          "name": [
            "Laboratory of Plant Physiology, Wageningen University and Research, Droevendaalsesteeg 1, 6708 PB, Wageningen, The Netherlands"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Beyraghdar Kashkooli", 
        "givenName": "Arman", 
        "id": "sg:person.014043574113.09", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.014043574113.09"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Department of Biochemistry and Physiology, Faculty of Pharmacy and Food Sciences, University of Barcelona, Campus Diagonal, Av. de Joan XXIII, 27-31, 08028, Barcelona, Spain", 
          "id": "http://www.grid.ac/institutes/grid.5841.8", 
          "name": [
            "Plant Metabolism and Metabolic Engineering Program, Centre for Research in Agricultural Genomics (CRAG) (CSIC-IRTA-UAB-UB), 08193, Barcelona, Spain", 
            "Department of Biochemistry and Physiology, Faculty of Pharmacy and Food Sciences, University of Barcelona, Campus Diagonal, Av. de Joan XXIII, 27-31, 08028, Barcelona, Spain"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Manzano", 
        "givenName": "David", 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Department of Plant and Environmental Sciences, University of Copenhagen, Thorvaldsensvej 40, 1871, Frederiksberg, Denmark", 
          "id": "http://www.grid.ac/institutes/grid.5254.6", 
          "name": [
            "Department of Plant and Environmental Sciences, University of Copenhagen, Thorvaldsensvej 40, 1871, Frederiksberg, Denmark"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Pateraki", 
        "givenName": "Irini", 
        "id": "sg:person.01353262162.36", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01353262162.36"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Laboratory of Plant Physiology, Wageningen University and Research, Droevendaalsesteeg 1, 6708 PB, Wageningen, The Netherlands", 
          "id": "http://www.grid.ac/institutes/grid.4818.5", 
          "name": [
            "Laboratory of Plant Physiology, Wageningen University and Research, Droevendaalsesteeg 1, 6708 PB, Wageningen, The Netherlands"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Richard", 
        "givenName": "Lea", 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Laboratory of Plant Physiology, Wageningen University and Research, Droevendaalsesteeg 1, 6708 PB, Wageningen, The Netherlands", 
          "id": "http://www.grid.ac/institutes/grid.4818.5", 
          "name": [
            "Laboratory of Plant Physiology, Wageningen University and Research, Droevendaalsesteeg 1, 6708 PB, Wageningen, The Netherlands"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Kolkman", 
        "givenName": "Pim", 
        "id": "sg:person.01120066235.46", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01120066235.46"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Barcelona Supercomputing Center (BSC), C/ Jordi Girona 29, 08034, Barcelona, Spain", 
          "id": "http://www.grid.ac/institutes/grid.10097.3f", 
          "name": [
            "Barcelona Supercomputing Center (BSC), C/ Jordi Girona 29, 08034, Barcelona, Spain"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Lucas", 
        "givenName": "Maria F\u00e1tima", 
        "id": "sg:person.01067265003.79", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01067265003.79"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "ICREA, Pg Llu\u00eds Companys 23, 08010, Barcelona, Spain", 
          "id": "http://www.grid.ac/institutes/grid.425902.8", 
          "name": [
            "Barcelona Supercomputing Center (BSC), C/ Jordi Girona 29, 08034, Barcelona, Spain", 
            "ICREA, Pg Llu\u00eds Companys 23, 08010, Barcelona, Spain"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Guallar", 
        "givenName": "Victor", 
        "id": "sg:person.01225760653.26", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01225760653.26"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Wageningen Plant Research, Wageningen University and Research, Droevendaalsesteeg 1, 6708 PB, Wageningen, The Netherlands", 
          "id": "http://www.grid.ac/institutes/grid.4818.5", 
          "name": [
            "Wageningen Plant Research, Wageningen University and Research, Droevendaalsesteeg 1, 6708 PB, Wageningen, The Netherlands"
          ], 
          "type": "Organization"
        }, 
        "familyName": "de Vos", 
        "givenName": "Ric C.H.", 
        "id": "sg:person.014575024362.22", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.014575024362.22"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Laboratory of Organic Chemistry, Wageningen University, Stippeneng 4, 6708 WE, Wageningen, The Netherlands", 
          "id": "http://www.grid.ac/institutes/grid.4818.5", 
          "name": [
            "Laboratory of Organic Chemistry, Wageningen University, Stippeneng 4, 6708 WE, Wageningen, The Netherlands"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Franssen", 
        "givenName": "Maurice C. R.", 
        "id": "sg:person.012053420354.70", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.012053420354.70"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Laboratory of Plant Physiology, Wageningen University and Research, Droevendaalsesteeg 1, 6708 PB, Wageningen, The Netherlands", 
          "id": "http://www.grid.ac/institutes/grid.4818.5", 
          "name": [
            "Laboratory of Plant Physiology, Wageningen University and Research, Droevendaalsesteeg 1, 6708 PB, Wageningen, The Netherlands"
          ], 
          "type": "Organization"
        }, 
        "familyName": "van der Krol", 
        "givenName": "Alexander", 
        "id": "sg:person.0626255112.97", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.0626255112.97"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Plant Hormone Biology group, Swammerdam Institute for Life Sciences, University of Amsterdam, Science Park 904, 1098 XH, Amsterdam, The Netherlands", 
          "id": "http://www.grid.ac/institutes/grid.7177.6", 
          "name": [
            "Laboratory of Plant Physiology, Wageningen University and Research, Droevendaalsesteeg 1, 6708 PB, Wageningen, The Netherlands", 
            "Plant Hormone Biology group, Swammerdam Institute for Life Sciences, University of Amsterdam, Science Park 904, 1098 XH, Amsterdam, The Netherlands"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Bouwmeester", 
        "givenName": "Harro", 
        "id": "sg:person.01170352102.67", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01170352102.67"
        ], 
        "type": "Person"
      }
    ], 
    "citation": [
      {
        "id": "sg:pub.10.1186/gb-2009-10-3-r25", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1049583368", 
          "https://doi.org/10.1186/gb-2009-10-3-r25"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "sg:pub.10.1007/bf01969123", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1000341507", 
          "https://doi.org/10.1007/bf01969123"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "sg:pub.10.1186/1479-7364-4-1-59", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1036064711", 
          "https://doi.org/10.1186/1479-7364-4-1-59"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "sg:pub.10.1038/nature12051", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1031919714", 
          "https://doi.org/10.1038/nature12051"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "sg:pub.10.1038/nprot.2008.73", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1005355981", 
          "https://doi.org/10.1038/nprot.2008.73"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "sg:pub.10.1186/gb-2010-11-10-r106", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1031289083", 
          "https://doi.org/10.1186/gb-2010-11-10-r106"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "sg:pub.10.1023/a:1014423510794", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1018085588", 
          "https://doi.org/10.1023/a:1014423510794"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "sg:pub.10.1007/978-3-7091-8548-3_2", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1022641255", 
          "https://doi.org/10.1007/978-3-7091-8548-3_2"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "sg:pub.10.1038/nature04640", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1006120611", 
          "https://doi.org/10.1038/nature04640"
        ], 
        "type": "CreativeWork"
      }
    ], 
    "datePublished": "2018-11-07", 
    "datePublishedReg": "2018-11-07", 
    "description": "Guaianolides are an important class of sesquiterpene lactones with unique biological and pharmaceutical properties. They have been postulated to be derived from germacranolides, but for years no progress has been made in the elucidation of their biosynthesis that requires an unknown cyclization mechanism. Here we demonstrate the isolation and characterization of a cytochrome P450 from feverfew (Tanacetum parthenium), kauniolide synthase. Kauniolide synthase catalyses the formation of the guaianolide kauniolide from the germacranolide substrate costunolide. Unlike most cytochrome P450s, kauniolide synthase combines stereoselective hydroxylation of costunolide at the C3 position, with water elimination, cyclization and regioselective deprotonation. This unique mechanism of action is supported by in silico modelling and docking experiments. The full kauniolide biosynthesis pathway is reconstructed in the heterologous hosts Nicotiana benthamiana and yeast, paving the way for biotechnological production of guaianolide-type sesquiterpene lactones.", 
    "genre": "article", 
    "id": "sg:pub.10.1038/s41467-018-06565-8", 
    "inLanguage": "en", 
    "isAccessibleForFree": true, 
    "isFundedItemOf": [
      {
        "id": "sg:grant.3775391", 
        "type": "MonetaryGrant"
      }
    ], 
    "isPartOf": [
      {
        "id": "sg:journal.1043282", 
        "issn": [
          "2041-1723"
        ], 
        "name": "Nature Communications", 
        "publisher": "Springer Nature", 
        "type": "Periodical"
      }, 
      {
        "issueNumber": "1", 
        "type": "PublicationIssue"
      }, 
      {
        "type": "PublicationVolume", 
        "volumeNumber": "9"
      }
    ], 
    "keywords": [
      "Nicotiana benthamiana", 
      "biosynthesis pathway", 
      "cytochrome P450", 
      "Most cytochrome P450", 
      "biotechnological production", 
      "sesquiterpene lactones", 
      "synthase", 
      "unique mechanism", 
      "cyclization mechanism", 
      "silico modelling", 
      "stereoselective hydroxylation", 
      "P450", 
      "unusual hydroxylation", 
      "benthamiana", 
      "biosynthesis", 
      "yeast", 
      "hydroxylation", 
      "costunolide", 
      "lactone", 
      "pathway", 
      "mechanism", 
      "pharmaceutical properties", 
      "elucidation", 
      "important class", 
      "isolation", 
      "germacranolides", 
      "production", 
      "C3 position", 
      "characterization", 
      "activity", 
      "formation", 
      "guaianolides", 
      "action", 
      "guaianolide-type sesquiterpene lactones", 
      "progress", 
      "regioselective deprotonation", 
      "experiments", 
      "water elimination", 
      "class", 
      "position", 
      "elimination", 
      "deprotonation", 
      "years", 
      "properties", 
      "way", 
      "modelling", 
      "cyclization"
    ], 
    "name": "Kauniolide synthase is a P450 with unusual hydroxylation and cyclization-elimination activity", 
    "pagination": "4657", 
    "productId": [
      {
        "name": "dimensions_id", 
        "type": "PropertyValue", 
        "value": [
          "pub.1107969567"
        ]
      }, 
      {
        "name": "doi", 
        "type": "PropertyValue", 
        "value": [
          "10.1038/s41467-018-06565-8"
        ]
      }, 
      {
        "name": "pubmed_id", 
        "type": "PropertyValue", 
        "value": [
          "30405138"
        ]
      }
    ], 
    "sameAs": [
      "https://doi.org/10.1038/s41467-018-06565-8", 
      "https://app.dimensions.ai/details/publication/pub.1107969567"
    ], 
    "sdDataset": "articles", 
    "sdDatePublished": "2022-05-20T07:34", 
    "sdLicense": "https://scigraph.springernature.com/explorer/license/", 
    "sdPublisher": {
      "name": "Springer Nature - SN SciGraph project", 
      "type": "Organization"
    }, 
    "sdSource": "s3://com-springernature-scigraph/baseset/20220519/entities/gbq_results/article/article_763.jsonl", 
    "type": "ScholarlyArticle", 
    "url": "https://doi.org/10.1038/s41467-018-06565-8"
  }
]
 

Download the RDF metadata as:  json-ld nt turtle xml License info

HOW TO GET THIS DATA PROGRAMMATICALLY:

JSON-LD is a popular format for linked data which is fully compatible with JSON.

curl -H 'Accept: application/ld+json' 'https://scigraph.springernature.com/pub.10.1038/s41467-018-06565-8'

N-Triples is a line-based linked data format ideal for batch operations.

curl -H 'Accept: application/n-triples' 'https://scigraph.springernature.com/pub.10.1038/s41467-018-06565-8'

Turtle is a human-readable linked data format.

curl -H 'Accept: text/turtle' 'https://scigraph.springernature.com/pub.10.1038/s41467-018-06565-8'

RDF/XML is a standard XML format for linked data.

curl -H 'Accept: application/rdf+xml' 'https://scigraph.springernature.com/pub.10.1038/s41467-018-06565-8'


 

This table displays all metadata directly associated to this object as RDF triples.

280 TRIPLES      22 PREDICATES      91 URIs      74 LITERALS      16 BLANK NODES

Subject Predicate Object
1 sg:pub.10.1038/s41467-018-06565-8 schema:about N33bf3cf20beb4c8db3e03265e489b3e4
2 N47fecdeb8dfb463ab1d136991cdac00a
3 N52304cef51834475a12899e30acbf6fd
4 N544ba1ed51de442b9c5c8f09ac25bc5d
5 N5a88e2b5c87f4bec8574e40f8f8d46bb
6 N5f9f3ac326c049d18ab3aad31fdea906
7 N6ceed8b9951b45a1892307bf2f5273ef
8 N90e78f574d484d06b2a77cbeda6d2db4
9 Nb0793e6c2da94ee0904c11cdbd1c5301
10 anzsrc-for:06
11 anzsrc-for:0601
12 schema:author N4d8f582eead0484d857949886e923408
13 schema:citation sg:pub.10.1007/978-3-7091-8548-3_2
14 sg:pub.10.1007/bf01969123
15 sg:pub.10.1023/a:1014423510794
16 sg:pub.10.1038/nature04640
17 sg:pub.10.1038/nature12051
18 sg:pub.10.1038/nprot.2008.73
19 sg:pub.10.1186/1479-7364-4-1-59
20 sg:pub.10.1186/gb-2009-10-3-r25
21 sg:pub.10.1186/gb-2010-11-10-r106
22 schema:datePublished 2018-11-07
23 schema:datePublishedReg 2018-11-07
24 schema:description Guaianolides are an important class of sesquiterpene lactones with unique biological and pharmaceutical properties. They have been postulated to be derived from germacranolides, but for years no progress has been made in the elucidation of their biosynthesis that requires an unknown cyclization mechanism. Here we demonstrate the isolation and characterization of a cytochrome P450 from feverfew (Tanacetum parthenium), kauniolide synthase. Kauniolide synthase catalyses the formation of the guaianolide kauniolide from the germacranolide substrate costunolide. Unlike most cytochrome P450s, kauniolide synthase combines stereoselective hydroxylation of costunolide at the C3 position, with water elimination, cyclization and regioselective deprotonation. This unique mechanism of action is supported by in silico modelling and docking experiments. The full kauniolide biosynthesis pathway is reconstructed in the heterologous hosts Nicotiana benthamiana and yeast, paving the way for biotechnological production of guaianolide-type sesquiterpene lactones.
25 schema:genre article
26 schema:inLanguage en
27 schema:isAccessibleForFree true
28 schema:isPartOf N09b6009731304a0291db1c18baab629f
29 N5fcf0f66804b49209cbd702e828db050
30 sg:journal.1043282
31 schema:keywords C3 position
32 Most cytochrome P450
33 Nicotiana benthamiana
34 P450
35 action
36 activity
37 benthamiana
38 biosynthesis
39 biosynthesis pathway
40 biotechnological production
41 characterization
42 class
43 costunolide
44 cyclization
45 cyclization mechanism
46 cytochrome P450
47 deprotonation
48 elimination
49 elucidation
50 experiments
51 formation
52 germacranolides
53 guaianolide-type sesquiterpene lactones
54 guaianolides
55 hydroxylation
56 important class
57 isolation
58 lactone
59 mechanism
60 modelling
61 pathway
62 pharmaceutical properties
63 position
64 production
65 progress
66 properties
67 regioselective deprotonation
68 sesquiterpene lactones
69 silico modelling
70 stereoselective hydroxylation
71 synthase
72 unique mechanism
73 unusual hydroxylation
74 water elimination
75 way
76 years
77 yeast
78 schema:name Kauniolide synthase is a P450 with unusual hydroxylation and cyclization-elimination activity
79 schema:pagination 4657
80 schema:productId N27ef577e1a654a1f803b1c30f228b25c
81 N553ca1a153e84f88a9c6950a138ced92
82 Nd93bf1d99261420da1983993f6fc2848
83 schema:sameAs https://app.dimensions.ai/details/publication/pub.1107969567
84 https://doi.org/10.1038/s41467-018-06565-8
85 schema:sdDatePublished 2022-05-20T07:34
86 schema:sdLicense https://scigraph.springernature.com/explorer/license/
87 schema:sdPublisher N9bd1a582ae24494a9c5aa2254ce50867
88 schema:url https://doi.org/10.1038/s41467-018-06565-8
89 sgo:license sg:explorer/license/
90 sgo:sdDataset articles
91 rdf:type schema:ScholarlyArticle
92 N0224f9786ea84f98890e9830246bd7a1 rdf:first Nd766bb66a7974f74a47344121808d230
93 rdf:rest N3eed792dd818460299fde8c3524e25f2
94 N09b6009731304a0291db1c18baab629f schema:issueNumber 1
95 rdf:type schema:PublicationIssue
96 N179201c90edc48f6904c98f016b119cf rdf:first sg:person.01225760653.26
97 rdf:rest Nacdbbce1d32442fa9b955ef2eb1d606e
98 N21da999d1eb74e9bb5ba42fe07af9d18 rdf:first sg:person.0626255112.97
99 rdf:rest N6b4b39ee2612474999951626809549fb
100 N27ef577e1a654a1f803b1c30f228b25c schema:name dimensions_id
101 schema:value pub.1107969567
102 rdf:type schema:PropertyValue
103 N301aadd0b6cc4e418b236a249bcefb65 rdf:first sg:person.01120066235.46
104 rdf:rest N3acd12790e6d4baca37f7d372cb82382
105 N33bf3cf20beb4c8db3e03265e489b3e4 schema:inDefinedTermSet https://www.nlm.nih.gov/mesh/
106 schema:name Saccharomyces cerevisiae
107 rdf:type schema:DefinedTerm
108 N392876b22f884b2c9c67da3c02a11866 rdf:first sg:person.014043574113.09
109 rdf:rest N0224f9786ea84f98890e9830246bd7a1
110 N3acd12790e6d4baca37f7d372cb82382 rdf:first sg:person.01067265003.79
111 rdf:rest N179201c90edc48f6904c98f016b119cf
112 N3aed179bb1174f08a563b619eceedd9c rdf:first sg:person.012053420354.70
113 rdf:rest N21da999d1eb74e9bb5ba42fe07af9d18
114 N3eed792dd818460299fde8c3524e25f2 rdf:first sg:person.01353262162.36
115 rdf:rest N705ae8bb0d9046e78a17e514bad99648
116 N47fecdeb8dfb463ab1d136991cdac00a schema:inDefinedTermSet https://www.nlm.nih.gov/mesh/
117 schema:name Tanacetum
118 rdf:type schema:DefinedTerm
119 N4d8f582eead0484d857949886e923408 rdf:first sg:person.01341013542.98
120 rdf:rest N392876b22f884b2c9c67da3c02a11866
121 N52304cef51834475a12899e30acbf6fd schema:inDefinedTermSet https://www.nlm.nih.gov/mesh/
122 schema:name Hydroxylation
123 rdf:type schema:DefinedTerm
124 N544ba1ed51de442b9c5c8f09ac25bc5d schema:inDefinedTermSet https://www.nlm.nih.gov/mesh/
125 schema:name Cyclization
126 rdf:type schema:DefinedTerm
127 N553ca1a153e84f88a9c6950a138ced92 schema:name doi
128 schema:value 10.1038/s41467-018-06565-8
129 rdf:type schema:PropertyValue
130 N5a88e2b5c87f4bec8574e40f8f8d46bb schema:inDefinedTermSet https://www.nlm.nih.gov/mesh/
131 schema:name Sesquiterpenes
132 rdf:type schema:DefinedTerm
133 N5f9f3ac326c049d18ab3aad31fdea906 schema:inDefinedTermSet https://www.nlm.nih.gov/mesh/
134 schema:name Biosynthetic Pathways
135 rdf:type schema:DefinedTerm
136 N5fcf0f66804b49209cbd702e828db050 schema:volumeNumber 9
137 rdf:type schema:PublicationVolume
138 N6b4b39ee2612474999951626809549fb rdf:first sg:person.01170352102.67
139 rdf:rest rdf:nil
140 N6ceed8b9951b45a1892307bf2f5273ef schema:inDefinedTermSet https://www.nlm.nih.gov/mesh/
141 schema:name Cytochrome P-450 Enzyme System
142 rdf:type schema:DefinedTerm
143 N705ae8bb0d9046e78a17e514bad99648 rdf:first N737bfc79c28d4dae9477aa10aa33dab7
144 rdf:rest N301aadd0b6cc4e418b236a249bcefb65
145 N737bfc79c28d4dae9477aa10aa33dab7 schema:affiliation grid-institutes:grid.4818.5
146 schema:familyName Richard
147 schema:givenName Lea
148 rdf:type schema:Person
149 N90e78f574d484d06b2a77cbeda6d2db4 schema:inDefinedTermSet https://www.nlm.nih.gov/mesh/
150 schema:name Molecular Docking Simulation
151 rdf:type schema:DefinedTerm
152 N9bd1a582ae24494a9c5aa2254ce50867 schema:name Springer Nature - SN SciGraph project
153 rdf:type schema:Organization
154 Nacdbbce1d32442fa9b955ef2eb1d606e rdf:first sg:person.014575024362.22
155 rdf:rest N3aed179bb1174f08a563b619eceedd9c
156 Nb0793e6c2da94ee0904c11cdbd1c5301 schema:inDefinedTermSet https://www.nlm.nih.gov/mesh/
157 schema:name Tobacco
158 rdf:type schema:DefinedTerm
159 Nd766bb66a7974f74a47344121808d230 schema:affiliation grid-institutes:grid.5841.8
160 schema:familyName Manzano
161 schema:givenName David
162 rdf:type schema:Person
163 Nd93bf1d99261420da1983993f6fc2848 schema:name pubmed_id
164 schema:value 30405138
165 rdf:type schema:PropertyValue
166 anzsrc-for:06 schema:inDefinedTermSet anzsrc-for:
167 schema:name Biological Sciences
168 rdf:type schema:DefinedTerm
169 anzsrc-for:0601 schema:inDefinedTermSet anzsrc-for:
170 schema:name Biochemistry and Cell Biology
171 rdf:type schema:DefinedTerm
172 sg:grant.3775391 http://pending.schema.org/fundedItem sg:pub.10.1038/s41467-018-06565-8
173 rdf:type schema:MonetaryGrant
174 sg:journal.1043282 schema:issn 2041-1723
175 schema:name Nature Communications
176 schema:publisher Springer Nature
177 rdf:type schema:Periodical
178 sg:person.01067265003.79 schema:affiliation grid-institutes:grid.10097.3f
179 schema:familyName Lucas
180 schema:givenName Maria Fátima
181 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01067265003.79
182 rdf:type schema:Person
183 sg:person.01120066235.46 schema:affiliation grid-institutes:grid.4818.5
184 schema:familyName Kolkman
185 schema:givenName Pim
186 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01120066235.46
187 rdf:type schema:Person
188 sg:person.01170352102.67 schema:affiliation grid-institutes:grid.7177.6
189 schema:familyName Bouwmeester
190 schema:givenName Harro
191 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01170352102.67
192 rdf:type schema:Person
193 sg:person.012053420354.70 schema:affiliation grid-institutes:grid.4818.5
194 schema:familyName Franssen
195 schema:givenName Maurice C. R.
196 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.012053420354.70
197 rdf:type schema:Person
198 sg:person.01225760653.26 schema:affiliation grid-institutes:grid.425902.8
199 schema:familyName Guallar
200 schema:givenName Victor
201 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01225760653.26
202 rdf:type schema:Person
203 sg:person.01341013542.98 schema:affiliation grid-institutes:grid.5254.6
204 schema:familyName Liu
205 schema:givenName Qing
206 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01341013542.98
207 rdf:type schema:Person
208 sg:person.01353262162.36 schema:affiliation grid-institutes:grid.5254.6
209 schema:familyName Pateraki
210 schema:givenName Irini
211 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01353262162.36
212 rdf:type schema:Person
213 sg:person.014043574113.09 schema:affiliation grid-institutes:grid.4818.5
214 schema:familyName Beyraghdar Kashkooli
215 schema:givenName Arman
216 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.014043574113.09
217 rdf:type schema:Person
218 sg:person.014575024362.22 schema:affiliation grid-institutes:grid.4818.5
219 schema:familyName de Vos
220 schema:givenName Ric C.H.
221 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.014575024362.22
222 rdf:type schema:Person
223 sg:person.0626255112.97 schema:affiliation grid-institutes:grid.4818.5
224 schema:familyName van der Krol
225 schema:givenName Alexander
226 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.0626255112.97
227 rdf:type schema:Person
228 sg:pub.10.1007/978-3-7091-8548-3_2 schema:sameAs https://app.dimensions.ai/details/publication/pub.1022641255
229 https://doi.org/10.1007/978-3-7091-8548-3_2
230 rdf:type schema:CreativeWork
231 sg:pub.10.1007/bf01969123 schema:sameAs https://app.dimensions.ai/details/publication/pub.1000341507
232 https://doi.org/10.1007/bf01969123
233 rdf:type schema:CreativeWork
234 sg:pub.10.1023/a:1014423510794 schema:sameAs https://app.dimensions.ai/details/publication/pub.1018085588
235 https://doi.org/10.1023/a:1014423510794
236 rdf:type schema:CreativeWork
237 sg:pub.10.1038/nature04640 schema:sameAs https://app.dimensions.ai/details/publication/pub.1006120611
238 https://doi.org/10.1038/nature04640
239 rdf:type schema:CreativeWork
240 sg:pub.10.1038/nature12051 schema:sameAs https://app.dimensions.ai/details/publication/pub.1031919714
241 https://doi.org/10.1038/nature12051
242 rdf:type schema:CreativeWork
243 sg:pub.10.1038/nprot.2008.73 schema:sameAs https://app.dimensions.ai/details/publication/pub.1005355981
244 https://doi.org/10.1038/nprot.2008.73
245 rdf:type schema:CreativeWork
246 sg:pub.10.1186/1479-7364-4-1-59 schema:sameAs https://app.dimensions.ai/details/publication/pub.1036064711
247 https://doi.org/10.1186/1479-7364-4-1-59
248 rdf:type schema:CreativeWork
249 sg:pub.10.1186/gb-2009-10-3-r25 schema:sameAs https://app.dimensions.ai/details/publication/pub.1049583368
250 https://doi.org/10.1186/gb-2009-10-3-r25
251 rdf:type schema:CreativeWork
252 sg:pub.10.1186/gb-2010-11-10-r106 schema:sameAs https://app.dimensions.ai/details/publication/pub.1031289083
253 https://doi.org/10.1186/gb-2010-11-10-r106
254 rdf:type schema:CreativeWork
255 grid-institutes:grid.10097.3f schema:alternateName Barcelona Supercomputing Center (BSC), C/ Jordi Girona 29, 08034, Barcelona, Spain
256 schema:name Barcelona Supercomputing Center (BSC), C/ Jordi Girona 29, 08034, Barcelona, Spain
257 rdf:type schema:Organization
258 grid-institutes:grid.425902.8 schema:alternateName ICREA, Pg Lluís Companys 23, 08010, Barcelona, Spain
259 schema:name Barcelona Supercomputing Center (BSC), C/ Jordi Girona 29, 08034, Barcelona, Spain
260 ICREA, Pg Lluís Companys 23, 08010, Barcelona, Spain
261 rdf:type schema:Organization
262 grid-institutes:grid.4818.5 schema:alternateName Laboratory of Organic Chemistry, Wageningen University, Stippeneng 4, 6708 WE, Wageningen, The Netherlands
263 Laboratory of Plant Physiology, Wageningen University and Research, Droevendaalsesteeg 1, 6708 PB, Wageningen, The Netherlands
264 Wageningen Plant Research, Wageningen University and Research, Droevendaalsesteeg 1, 6708 PB, Wageningen, The Netherlands
265 schema:name Laboratory of Organic Chemistry, Wageningen University, Stippeneng 4, 6708 WE, Wageningen, The Netherlands
266 Laboratory of Plant Physiology, Wageningen University and Research, Droevendaalsesteeg 1, 6708 PB, Wageningen, The Netherlands
267 Wageningen Plant Research, Wageningen University and Research, Droevendaalsesteeg 1, 6708 PB, Wageningen, The Netherlands
268 rdf:type schema:Organization
269 grid-institutes:grid.5254.6 schema:alternateName Department of Plant and Environmental Sciences, University of Copenhagen, Thorvaldsensvej 40, 1871, Frederiksberg, Denmark
270 schema:name Department of Plant and Environmental Sciences, University of Copenhagen, Thorvaldsensvej 40, 1871, Frederiksberg, Denmark
271 Laboratory of Plant Physiology, Wageningen University and Research, Droevendaalsesteeg 1, 6708 PB, Wageningen, The Netherlands
272 rdf:type schema:Organization
273 grid-institutes:grid.5841.8 schema:alternateName Department of Biochemistry and Physiology, Faculty of Pharmacy and Food Sciences, University of Barcelona, Campus Diagonal, Av. de Joan XXIII, 27-31, 08028, Barcelona, Spain
274 schema:name Department of Biochemistry and Physiology, Faculty of Pharmacy and Food Sciences, University of Barcelona, Campus Diagonal, Av. de Joan XXIII, 27-31, 08028, Barcelona, Spain
275 Plant Metabolism and Metabolic Engineering Program, Centre for Research in Agricultural Genomics (CRAG) (CSIC-IRTA-UAB-UB), 08193, Barcelona, Spain
276 rdf:type schema:Organization
277 grid-institutes:grid.7177.6 schema:alternateName Plant Hormone Biology group, Swammerdam Institute for Life Sciences, University of Amsterdam, Science Park 904, 1098 XH, Amsterdam, The Netherlands
278 schema:name Laboratory of Plant Physiology, Wageningen University and Research, Droevendaalsesteeg 1, 6708 PB, Wageningen, The Netherlands
279 Plant Hormone Biology group, Swammerdam Institute for Life Sciences, University of Amsterdam, Science Park 904, 1098 XH, Amsterdam, The Netherlands
280 rdf:type schema:Organization
 




Preview window. Press ESC to close (or click here)


...