Ontology type: schema:ScholarlyArticle
2010-04-15
AUTHORSHua-Ping Dong, Zhi-Qiang Liu, Yu-Guo Zheng, Yin-Chu Shen
ABSTRACT(R)-ethyl-3-hydroxyglutarate with highly optical purity (≥99%) can be used as a novel precursor for synthesis of chiral side chain of rosuvastatin. In this study, a novel synthesis route of (R)-ethyl-3-hydroxyglutarate by whole microorganism cells from racemic ethyl 4-cyano-3-hydroxybutyate was created. A strain ZJB-0910 capable of transforming racemic β-hydroxy aliphatic nitrile was isolated by employing a screening method based on a colorimetric reaction of Co2+ ion with ammonia, and identified as Rhodococcus erythropolis based on its morphology, physiological tests, Biolog, and the 16S rDNA sequence. After cultivation in a sterilized medium with composition of 20 g glucose, 5 g yeast extract, 0.5 g KH2PO4, 0.5 g K2HPO4, 0.2 g MgSO4·7H2O per liter at 30°C and 150 rpm for 48 h, the whole cells of R. erythropolis ZJB-0910 were prepared as a catalyst in (R)-enantioselective hydrolysis of racemic ethyl 4-cyano-3-hydroxybutyate for synthesis of (R)-ethyl-3-hydroxyglutarate, without bearing hydrolase activity for the ester bond of ethyl 4-cyano-3-hydroxybutyate. Under the optimized biotransformation conditions of pH 7.5, 30°C, and 20 mM substrate concentration, (R)-ethyl-3-hydroxyglutarate with 46.2% yield (ee > 99%) was afforded, and its chemical structure was determined by ESI-MS, NMR, and IR. The apparent Michaelis constant Km and maximum rate Vmax for this biocatalytic reaction were 0.01 M and 85.6 μmol min−1 g−1, respectively. More... »
PAGES1335-1345
http://scigraph.springernature.com/pub.10.1007/s00253-010-2584-5
DOIhttp://dx.doi.org/10.1007/s00253-010-2584-5
DIMENSIONShttps://app.dimensions.ai/details/publication/pub.1052610166
PUBMEDhttps://www.ncbi.nlm.nih.gov/pubmed/20393698
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/2008/03",
"inDefinedTermSet": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/",
"name": "Chemical Sciences",
"type": "DefinedTerm"
},
{
"id": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/0305",
"inDefinedTermSet": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/",
"name": "Organic Chemistry",
"type": "DefinedTerm"
},
{
"id": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/0306",
"inDefinedTermSet": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/",
"name": "Physical Chemistry (incl. Structural)",
"type": "DefinedTerm"
},
{
"inDefinedTermSet": "https://www.nlm.nih.gov/mesh/",
"name": "Biotransformation",
"type": "DefinedTerm"
},
{
"inDefinedTermSet": "https://www.nlm.nih.gov/mesh/",
"name": "Glutarates",
"type": "DefinedTerm"
},
{
"inDefinedTermSet": "https://www.nlm.nih.gov/mesh/",
"name": "Hydrolysis",
"type": "DefinedTerm"
},
{
"inDefinedTermSet": "https://www.nlm.nih.gov/mesh/",
"name": "Molecular Sequence Data",
"type": "DefinedTerm"
},
{
"inDefinedTermSet": "https://www.nlm.nih.gov/mesh/",
"name": "Phylogeny",
"type": "DefinedTerm"
},
{
"inDefinedTermSet": "https://www.nlm.nih.gov/mesh/",
"name": "Rhodococcus",
"type": "DefinedTerm"
},
{
"inDefinedTermSet": "https://www.nlm.nih.gov/mesh/",
"name": "Soil Microbiology",
"type": "DefinedTerm"
},
{
"inDefinedTermSet": "https://www.nlm.nih.gov/mesh/",
"name": "Stereoisomerism",
"type": "DefinedTerm"
}
],
"author": [
{
"affiliation": {
"alternateName": "Institute of Chemistry and Chemical Engineering, Shaoxing University, 312000, Shaoxing, Zhejiang, People\u2019s Republic of China",
"id": "http://www.grid.ac/institutes/grid.412551.6",
"name": [
"Institute of Bioengineering, Zhejiang University of Technology, 310014, Hangzhou, Zhejiang, People\u2019s Republic of China",
"Institute of Chemistry and Chemical Engineering, Shaoxing University, 312000, Shaoxing, Zhejiang, People\u2019s Republic of China"
],
"type": "Organization"
},
"familyName": "Dong",
"givenName": "Hua-Ping",
"id": "sg:person.07467305426.99",
"sameAs": [
"https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.07467305426.99"
],
"type": "Person"
},
{
"affiliation": {
"alternateName": "Institute of Bioengineering, Zhejiang University of Technology, 310014, Hangzhou, Zhejiang, People\u2019s Republic of China",
"id": "http://www.grid.ac/institutes/grid.469325.f",
"name": [
"Institute of Bioengineering, Zhejiang University of Technology, 310014, Hangzhou, Zhejiang, People\u2019s Republic of China"
],
"type": "Organization"
},
"familyName": "Liu",
"givenName": "Zhi-Qiang",
"id": "sg:person.01256734541.85",
"sameAs": [
"https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01256734541.85"
],
"type": "Person"
},
{
"affiliation": {
"alternateName": "Institute of Bioengineering, Zhejiang University of Technology, 310014, Hangzhou, Zhejiang, People\u2019s Republic of China",
"id": "http://www.grid.ac/institutes/grid.469325.f",
"name": [
"Institute of Bioengineering, Zhejiang University of Technology, 310014, Hangzhou, Zhejiang, People\u2019s Republic of China"
],
"type": "Organization"
},
"familyName": "Zheng",
"givenName": "Yu-Guo",
"id": "sg:person.01144225405.06",
"sameAs": [
"https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01144225405.06"
],
"type": "Person"
},
{
"affiliation": {
"alternateName": "Institute of Bioengineering, Zhejiang University of Technology, 310014, Hangzhou, Zhejiang, People\u2019s Republic of China",
"id": "http://www.grid.ac/institutes/grid.469325.f",
"name": [
"Institute of Bioengineering, Zhejiang University of Technology, 310014, Hangzhou, Zhejiang, People\u2019s Republic of China"
],
"type": "Organization"
},
"familyName": "Shen",
"givenName": "Yin-Chu",
"id": "sg:person.01072704134.44",
"sameAs": [
"https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01072704134.44"
],
"type": "Person"
}
],
"citation": [
{
"id": "sg:pub.10.1007/s10529-004-5320-3",
"sameAs": [
"https://app.dimensions.ai/details/publication/pub.1044857360",
"https://doi.org/10.1007/s10529-004-5320-3"
],
"type": "CreativeWork"
},
{
"id": "sg:pub.10.1007/10_2008_25",
"sameAs": [
"https://app.dimensions.ai/details/publication/pub.1031952913",
"https://doi.org/10.1007/10_2008_25"
],
"type": "CreativeWork"
},
{
"id": "sg:pub.10.1365/s10337-009-1401-8",
"sameAs": [
"https://app.dimensions.ai/details/publication/pub.1042110778",
"https://doi.org/10.1365/s10337-009-1401-8"
],
"type": "CreativeWork"
},
{
"id": "sg:pub.10.1007/s00253-009-1862-6",
"sameAs": [
"https://app.dimensions.ai/details/publication/pub.1008001925",
"https://doi.org/10.1007/s00253-009-1862-6"
],
"type": "CreativeWork"
},
{
"id": "sg:pub.10.1007/s11244-005-3817-1",
"sameAs": [
"https://app.dimensions.ai/details/publication/pub.1012803549",
"https://doi.org/10.1007/s11244-005-3817-1"
],
"type": "CreativeWork"
},
{
"id": "sg:pub.10.1007/s00253-009-2143-0",
"sameAs": [
"https://app.dimensions.ai/details/publication/pub.1043482154",
"https://doi.org/10.1007/s00253-009-2143-0"
],
"type": "CreativeWork"
},
{
"id": "sg:pub.10.1007/s00253-006-0642-9",
"sameAs": [
"https://app.dimensions.ai/details/publication/pub.1014627874",
"https://doi.org/10.1007/s00253-006-0642-9"
],
"type": "CreativeWork"
},
{
"id": "sg:pub.10.1007/s00253-008-1685-x",
"sameAs": [
"https://app.dimensions.ai/details/publication/pub.1045804765",
"https://doi.org/10.1007/s00253-008-1685-x"
],
"type": "CreativeWork"
},
{
"id": "sg:pub.10.1007/s00253-007-1236-x",
"sameAs": [
"https://app.dimensions.ai/details/publication/pub.1008191782",
"https://doi.org/10.1007/s00253-007-1236-x"
],
"type": "CreativeWork"
}
],
"datePublished": "2010-04-15",
"datePublishedReg": "2010-04-15",
"description": "Abstract(R)-ethyl-3-hydroxyglutarate with highly optical purity (\u226599%) can be used as a novel precursor for synthesis of chiral side chain of rosuvastatin. In this study, a novel synthesis route of (R)-ethyl-3-hydroxyglutarate by whole microorganism cells from racemic ethyl 4-cyano-3-hydroxybutyate was created. A strain ZJB-0910 capable of transforming racemic \u03b2-hydroxy aliphatic nitrile was isolated by employing a screening method based on a colorimetric reaction of Co2+ ion with ammonia, and identified as Rhodococcus erythropolis based on its morphology, physiological tests, Biolog, and the 16S rDNA sequence. After cultivation in a sterilized medium with composition of 20\u00a0g glucose, 5\u00a0g yeast extract, 0.5\u00a0g KH2PO4, 0.5\u00a0g K2HPO4, 0.2\u00a0g MgSO4\u00b77H2O per liter at 30\u00b0C and 150\u00a0rpm for 48\u00a0h, the whole cells of R. erythropolis ZJB-0910 were prepared as a catalyst in (R)-enantioselective hydrolysis of racemic ethyl 4-cyano-3-hydroxybutyate for synthesis of (R)-ethyl-3-hydroxyglutarate, without bearing hydrolase activity for the ester bond of ethyl 4-cyano-3-hydroxybutyate. Under the optimized biotransformation conditions of pH 7.5, 30\u00b0C, and 20 mM substrate concentration, (R)-ethyl-3-hydroxyglutarate with 46.2% yield (ee\u2009>\u200999%) was afforded, and its chemical structure was determined by ESI-MS, NMR, and IR. The apparent Michaelis constant Km and maximum rate Vmax for this biocatalytic reaction were 0.01\u00a0M and 85.6\u00a0\u03bcmol\u00a0min\u22121\u2009g\u22121, respectively.",
"genre": "article",
"id": "sg:pub.10.1007/s00253-010-2584-5",
"isAccessibleForFree": false,
"isPartOf": [
{
"id": "sg:journal.1083533",
"issn": [
"0175-7598",
"1432-0614"
],
"name": "Applied Microbiology and Biotechnology",
"publisher": "Springer Nature",
"type": "Periodical"
},
{
"issueNumber": "4",
"type": "PublicationIssue"
},
{
"type": "PublicationVolume",
"volumeNumber": "87"
}
],
"keywords": [
"ethyl 4",
"chiral side chains",
"novel synthesis route",
"maximum rate Vmax",
"apparent Michaelis constant Km",
"enantioselective hydrolysis",
"synthesis route",
"ESI-MS",
"chemical structure",
"biocatalytic reactions",
"novel biosynthesis",
"novel precursor",
"side chains",
"ester bond",
"aliphatic nitriles",
"Michaelis constant Km",
"optical purity",
"colorimetric reaction",
"Rhodococcus erythropolis",
"microorganism cells",
"synthesis",
"constant Km",
"reaction",
"hydrolysis",
"substrate concentration",
"catalyst",
"NMR",
"IR",
"nitriles",
"bonds",
"ions",
"screening method",
"ammonia",
"precursors",
"whole cells",
"purity",
"erythropolis",
"route",
"CO2",
"chain",
"morphology",
"yield",
"structure",
"composition",
"KH2PO4",
"concentration",
"K2HPO4",
"extract",
"hydrolase activity",
"biosynthesis",
"medium",
"activity",
"Km",
"biotransformation conditions",
"method",
"cells",
"rpm",
"conditions",
"glucose",
"yeast extract",
"Vmax",
"study",
"rosuvastatin",
"sequence",
"test",
"physiological tests",
"Biolog",
"cultivation",
"rDNA sequences"
],
"name": "Novel biosynthesis of (R)-ethyl-3-hydroxyglutarate with (R)-enantioselective hydrolysis of racemic ethyl 4-cyano-3-hydroxybutyate by Rhodococcus erythropolis",
"pagination": "1335-1345",
"productId": [
{
"name": "dimensions_id",
"type": "PropertyValue",
"value": [
"pub.1052610166"
]
},
{
"name": "doi",
"type": "PropertyValue",
"value": [
"10.1007/s00253-010-2584-5"
]
},
{
"name": "pubmed_id",
"type": "PropertyValue",
"value": [
"20393698"
]
}
],
"sameAs": [
"https://doi.org/10.1007/s00253-010-2584-5",
"https://app.dimensions.ai/details/publication/pub.1052610166"
],
"sdDataset": "articles",
"sdDatePublished": "2022-08-04T16:57",
"sdLicense": "https://scigraph.springernature.com/explorer/license/",
"sdPublisher": {
"name": "Springer Nature - SN SciGraph project",
"type": "Organization"
},
"sdSource": "s3://com-springernature-scigraph/baseset/20220804/entities/gbq_results/article/article_501.jsonl",
"type": "ScholarlyArticle",
"url": "https://doi.org/10.1007/s00253-010-2584-5"
}
]Download the RDF metadata as: json-ld nt turtle xml License info
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.10.1007/s00253-010-2584-5'
N-Triples is a line-based linked data format ideal for batch operations.
curl -H 'Accept: application/n-triples' 'https://scigraph.springernature.com/pub.10.1007/s00253-010-2584-5'
Turtle is a human-readable linked data format.
curl -H 'Accept: text/turtle' 'https://scigraph.springernature.com/pub.10.1007/s00253-010-2584-5'
RDF/XML is a standard XML format for linked data.
curl -H 'Accept: application/rdf+xml' 'https://scigraph.springernature.com/pub.10.1007/s00253-010-2584-5'
This table displays all metadata directly associated to this object as RDF triples.
227 TRIPLES
21 PREDICATES
112 URIs
94 LITERALS
15 BLANK NODES