Asymmetric synthesis of tert-butyl (3R,5S)-6-chloro-3,5-dihydroxyhexanoate using a self-sufficient biocatalyst based on carbonyl reductase and cofactor co-immobilization View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2019-09-21

AUTHORS

Xiao-Jian Zhang, Wen-Zhong Wang, Rong Zhou, Zhi-Qiang Liu, Yu-Guo Zheng

ABSTRACT

tert-Butyl (3R,5S)-6-chloro-3,5-dihydroxyhexanoate [(3R,5S)-CDHH] is the key chiral intermediate to synthesize the side chain of the lipid-lowering drug rosuvastatin. Carbonyl reductases showed excellent activity for the biosynthesis of (3R,5S)-CDHH. The requirement of cofactor NADH/NADPH leads to high cost for the industrial application of carbonyl reductases. In this study, a self-sufficient biocatalyst based on carbonyl reductase and NADP+ co-immobilization strategy was developed on an amino resin carrier LX-1000HAA (SCR-NADP+@LX-1000HAA). The self-sufficient biocatalyst achieved in situ cofactor regeneration and showed the activity recovery of 77.93% and the specific activity of 70.45 U/g. Asymmetric synthesis of (3R,5S)-CDHH using SCR-NADP+@LX-1000HAA showed high enantioselectivity (> 99% e.e.) and yield (98.54%). Batch reactions were performed for ten cycles without extra addition of NADP+, and the total yield of (3R,5S)-CDHH achieved at 10.56 g/g biocatalyst. The present work demonstrated the potential of the self-sufficient biocatalyst for the asymmetric biosynthesis of rosuvastatin intermediate.Graphic abstract More... »

PAGES

21-31

References to SciGraph publications

  • 2017-02-08. On the design of complex drug candidate syntheses in the pharmaceutical industry in NATURE REVIEWS CHEMISTRY
  • 2016-11-11. Carbonyl reductase identification and development of whole-cell biotransformation for highly efficient synthesis of (R)-[3,5-bis(trifluoromethyl)phenyl] ethanol in MICROBIAL CELL FACTORIES
  • 2004-12-22. Production of Lactobacillus kefir cells for asymmetric synthesis of a 3,5-dihydroxycarboxylate in APPLIED MICROBIOLOGY AND BIOTECHNOLOGY
  • 2017-10-24. Crystal structure and iterative saturation mutagenesis of ChKRED20 for expanded catalytic scope in APPLIED MICROBIOLOGY AND BIOTECHNOLOGY
  • 2005-02-19. Asymmetric synthesis of tert-butyl (3R, 5S) 6-chloro-dihydroxyhexanoate with Lactobacillus kefir in APPLIED MICROBIOLOGY AND BIOTECHNOLOGY
  • 2017-08-21. Asymmetric reduction of ketopantolactone using a strictly (R)-stereoselective carbonyl reductase through efficient NADPH regeneration and the substrate constant-feeding strategy in BIOTECHNOLOGY LETTERS
  • 2013-01. Bioconversion process for synthesis of tert-butyl (3R,5S)-6-chloro-3,5-dihydroxyhexanoate using liquid-core immobilized Saccharomyces cerevisiae CGMCC No 2233 in KOREAN JOURNAL OF CHEMICAL ENGINEERING
  • 2014-05-06. Asymmetric synthesis of duloxetine intermediate (S)-(-)-3-N-methylamino-1-(2-thienyl)-1-propanol using immobilized Saccharomyces cerevisiae in liquid-core sodium alginate/chitosan/sodium alginate microcapsules in BIOPROCESS AND BIOSYSTEMS ENGINEERING
  • 2017-01-10. Recent advances in biotechnological applications of alcohol dehydrogenases in APPLIED MICROBIOLOGY AND BIOTECHNOLOGY
  • 2017-06-08. Sortase A-mediated crosslinked short-chain dehydrogenases/reductases as novel biocatalysts with improved thermostability and catalytic efficiency in SCIENTIFIC REPORTS
  • 2015-05-26. Highly efficient enzymatic synthesis of tert-butyl (S)-6-chloro-5-hydroxy-3-oxohexanoate with a mutant alcohol dehydrogenase of Lactobacillus kefir in APPLIED MICROBIOLOGY AND BIOTECHNOLOGY
  • 2018-10-20. Development of an Efficient and Cost-Effective Enzymatic Process for Production of (R)-[3,5-bis(trifluoromethyl)phenyl] Ethanol Using Carbonyl Reductase Derived from Leifsonia sp. S749 in APPLIED BIOCHEMISTRY AND BIOTECHNOLOGY
  • 1970-08. Cleavage of Structural Proteins during the Assembly of the Head of Bacteriophage T4 in NATURE
  • 2008-02-21. Chemoenzymatic synthesis of the chiral side-chain of statins: application of an alcohol dehydrogenase catalysed ketone reduction on a large scale in BIOPROCESS AND BIOSYSTEMS ENGINEERING
  • Identifiers

    URI

    http://scigraph.springernature.com/pub.10.1007/s00449-019-02201-x

    DOI

    http://dx.doi.org/10.1007/s00449-019-02201-x

    DIMENSIONS

    https://app.dimensions.ai/details/publication/pub.1121176127

    PUBMED

    https://www.ncbi.nlm.nih.gov/pubmed/31542820


    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/2008/09", 
            "inDefinedTermSet": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/", 
            "name": "Engineering", 
            "type": "DefinedTerm"
          }, 
          {
            "id": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/10", 
            "inDefinedTermSet": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/", 
            "name": "Technology", 
            "type": "DefinedTerm"
          }, 
          {
            "id": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/0903", 
            "inDefinedTermSet": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/", 
            "name": "Biomedical Engineering", 
            "type": "DefinedTerm"
          }, 
          {
            "id": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/0904", 
            "inDefinedTermSet": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/", 
            "name": "Chemical Engineering", 
            "type": "DefinedTerm"
          }, 
          {
            "id": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/1003", 
            "inDefinedTermSet": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/", 
            "name": "Industrial Biotechnology", 
            "type": "DefinedTerm"
          }, 
          {
            "inDefinedTermSet": "https://www.nlm.nih.gov/mesh/", 
            "name": "Alcohol Oxidoreductases", 
            "type": "DefinedTerm"
          }, 
          {
            "inDefinedTermSet": "https://www.nlm.nih.gov/mesh/", 
            "name": "Biocatalysis", 
            "type": "DefinedTerm"
          }, 
          {
            "inDefinedTermSet": "https://www.nlm.nih.gov/mesh/", 
            "name": "Candida", 
            "type": "DefinedTerm"
          }, 
          {
            "inDefinedTermSet": "https://www.nlm.nih.gov/mesh/", 
            "name": "Caproates", 
            "type": "DefinedTerm"
          }, 
          {
            "inDefinedTermSet": "https://www.nlm.nih.gov/mesh/", 
            "name": "Enzymes, Immobilized", 
            "type": "DefinedTerm"
          }, 
          {
            "inDefinedTermSet": "https://www.nlm.nih.gov/mesh/", 
            "name": "Fungal Proteins", 
            "type": "DefinedTerm"
          }, 
          {
            "inDefinedTermSet": "https://www.nlm.nih.gov/mesh/", 
            "name": "NADP", 
            "type": "DefinedTerm"
          }, 
          {
            "inDefinedTermSet": "https://www.nlm.nih.gov/mesh/", 
            "name": "Recombinant Proteins", 
            "type": "DefinedTerm"
          }, 
          {
            "inDefinedTermSet": "https://www.nlm.nih.gov/mesh/", 
            "name": "Rosuvastatin Calcium", 
            "type": "DefinedTerm"
          }
        ], 
        "author": [
          {
            "affiliation": {
              "alternateName": "Key Laboratory of Bioorganic Synthesis of Zhejiang Province, College of Biotechnology and Bioengineering, Zhejiang University of Technology, 310014, Hangzhou, China", 
              "id": "http://www.grid.ac/institutes/grid.469325.f", 
              "name": [
                "Key Laboratory of Bioorganic Synthesis of Zhejiang Province, College of Biotechnology and Bioengineering, Zhejiang University of Technology, 310014, Hangzhou, China"
              ], 
              "type": "Organization"
            }, 
            "familyName": "Zhang", 
            "givenName": "Xiao-Jian", 
            "id": "sg:person.015254304653.17", 
            "sameAs": [
              "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.015254304653.17"
            ], 
            "type": "Person"
          }, 
          {
            "affiliation": {
              "alternateName": "Key Laboratory of Bioorganic Synthesis of Zhejiang Province, College of Biotechnology and Bioengineering, Zhejiang University of Technology, 310014, Hangzhou, China", 
              "id": "http://www.grid.ac/institutes/grid.469325.f", 
              "name": [
                "Key Laboratory of Bioorganic Synthesis of Zhejiang Province, College of Biotechnology and Bioengineering, Zhejiang University of Technology, 310014, Hangzhou, China"
              ], 
              "type": "Organization"
            }, 
            "familyName": "Wang", 
            "givenName": "Wen-Zhong", 
            "id": "sg:person.013506337743.10", 
            "sameAs": [
              "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.013506337743.10"
            ], 
            "type": "Person"
          }, 
          {
            "affiliation": {
              "alternateName": "Key Laboratory of Bioorganic Synthesis of Zhejiang Province, College of Biotechnology and Bioengineering, Zhejiang University of Technology, 310014, Hangzhou, China", 
              "id": "http://www.grid.ac/institutes/grid.469325.f", 
              "name": [
                "Key Laboratory of Bioorganic Synthesis of Zhejiang Province, College of Biotechnology and Bioengineering, Zhejiang University of Technology, 310014, Hangzhou, China"
              ], 
              "type": "Organization"
            }, 
            "familyName": "Zhou", 
            "givenName": "Rong", 
            "id": "sg:person.010602155114.51", 
            "sameAs": [
              "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.010602155114.51"
            ], 
            "type": "Person"
          }, 
          {
            "affiliation": {
              "alternateName": "Key Laboratory of Bioorganic Synthesis of Zhejiang Province, College of Biotechnology and Bioengineering, Zhejiang University of Technology, 310014, Hangzhou, China", 
              "id": "http://www.grid.ac/institutes/grid.469325.f", 
              "name": [
                "Key Laboratory of Bioorganic Synthesis of Zhejiang Province, College of Biotechnology and Bioengineering, Zhejiang University of Technology, 310014, Hangzhou, 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": "Key Laboratory of Bioorganic Synthesis of Zhejiang Province, College of Biotechnology and Bioengineering, Zhejiang University of Technology, 310014, Hangzhou, China", 
              "id": "http://www.grid.ac/institutes/grid.469325.f", 
              "name": [
                "Key Laboratory of Bioorganic Synthesis of Zhejiang Province, College of Biotechnology and Bioengineering, Zhejiang University of Technology, 310014, Hangzhou, 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"
          }
        ], 
        "citation": [
          {
            "id": "sg:pub.10.1007/s11814-012-0093-1", 
            "sameAs": [
              "https://app.dimensions.ai/details/publication/pub.1009746025", 
              "https://doi.org/10.1007/s11814-012-0093-1"
            ], 
            "type": "CreativeWork"
          }, 
          {
            "id": "sg:pub.10.1038/s41598-017-03168-z", 
            "sameAs": [
              "https://app.dimensions.ai/details/publication/pub.1085846261", 
              "https://doi.org/10.1038/s41598-017-03168-z"
            ], 
            "type": "CreativeWork"
          }, 
          {
            "id": "sg:pub.10.1007/s00449-008-0205-9", 
            "sameAs": [
              "https://app.dimensions.ai/details/publication/pub.1050406645", 
              "https://doi.org/10.1007/s00449-008-0205-9"
            ], 
            "type": "CreativeWork"
          }, 
          {
            "id": "sg:pub.10.1186/s12934-016-0585-5", 
            "sameAs": [
              "https://app.dimensions.ai/details/publication/pub.1034558571", 
              "https://doi.org/10.1186/s12934-016-0585-5"
            ], 
            "type": "CreativeWork"
          }, 
          {
            "id": "sg:pub.10.1007/s00253-017-8556-2", 
            "sameAs": [
              "https://app.dimensions.ai/details/publication/pub.1092340057", 
              "https://doi.org/10.1007/s00253-017-8556-2"
            ], 
            "type": "CreativeWork"
          }, 
          {
            "id": "sg:pub.10.1007/s00253-004-1837-6", 
            "sameAs": [
              "https://app.dimensions.ai/details/publication/pub.1037870387", 
              "https://doi.org/10.1007/s00253-004-1837-6"
            ], 
            "type": "CreativeWork"
          }, 
          {
            "id": "sg:pub.10.1007/s00253-015-6675-1", 
            "sameAs": [
              "https://app.dimensions.ai/details/publication/pub.1040837053", 
              "https://doi.org/10.1007/s00253-015-6675-1"
            ], 
            "type": "CreativeWork"
          }, 
          {
            "id": "sg:pub.10.1007/s00253-016-8083-6", 
            "sameAs": [
              "https://app.dimensions.ai/details/publication/pub.1050459052", 
              "https://doi.org/10.1007/s00253-016-8083-6"
            ], 
            "type": "CreativeWork"
          }, 
          {
            "id": "sg:pub.10.1007/s00449-014-1202-9", 
            "sameAs": [
              "https://app.dimensions.ai/details/publication/pub.1037510106", 
              "https://doi.org/10.1007/s00449-014-1202-9"
            ], 
            "type": "CreativeWork"
          }, 
          {
            "id": "sg:pub.10.1007/s12010-018-2904-2", 
            "sameAs": [
              "https://app.dimensions.ai/details/publication/pub.1107728294", 
              "https://doi.org/10.1007/s12010-018-2904-2"
            ], 
            "type": "CreativeWork"
          }, 
          {
            "id": "sg:pub.10.1038/s41570-017-0016", 
            "sameAs": [
              "https://app.dimensions.ai/details/publication/pub.1083742827", 
              "https://doi.org/10.1038/s41570-017-0016"
            ], 
            "type": "CreativeWork"
          }, 
          {
            "id": "sg:pub.10.1007/s00253-005-1921-6", 
            "sameAs": [
              "https://app.dimensions.ai/details/publication/pub.1005725582", 
              "https://doi.org/10.1007/s00253-005-1921-6"
            ], 
            "type": "CreativeWork"
          }, 
          {
            "id": "sg:pub.10.1038/227680a0", 
            "sameAs": [
              "https://app.dimensions.ai/details/publication/pub.1010419937", 
              "https://doi.org/10.1038/227680a0"
            ], 
            "type": "CreativeWork"
          }, 
          {
            "id": "sg:pub.10.1007/s10529-017-2415-1", 
            "sameAs": [
              "https://app.dimensions.ai/details/publication/pub.1091284948", 
              "https://doi.org/10.1007/s10529-017-2415-1"
            ], 
            "type": "CreativeWork"
          }
        ], 
        "datePublished": "2019-09-21", 
        "datePublishedReg": "2019-09-21", 
        "description": "Abstracttert-Butyl (3R,5S)-6-chloro-3,5-dihydroxyhexanoate [(3R,5S)-CDHH] is the key chiral intermediate to synthesize the side chain of the lipid-lowering drug rosuvastatin. Carbonyl reductases showed excellent activity for the biosynthesis of (3R,5S)-CDHH. The requirement of cofactor NADH/NADPH leads to high cost for the industrial application of carbonyl reductases. In this study, a self-sufficient biocatalyst based on carbonyl reductase and NADP+ co-immobilization strategy was developed on an amino resin carrier LX-1000HAA (SCR-NADP+@LX-1000HAA). The self-sufficient biocatalyst achieved in situ cofactor regeneration and showed the activity recovery of 77.93% and the specific activity of 70.45\u00a0U/g. Asymmetric synthesis of (3R,5S)-CDHH using SCR-NADP+@LX-1000HAA showed high enantioselectivity (>\u00a099% e.e.) and yield (98.54%). Batch reactions were performed for ten cycles without extra addition of NADP+, and the total yield of (3R,5S)-CDHH achieved at 10.56\u00a0g/g biocatalyst. The present work demonstrated the potential of the self-sufficient biocatalyst for the asymmetric biosynthesis of rosuvastatin intermediate.Graphic abstract", 
        "genre": "article", 
        "id": "sg:pub.10.1007/s00449-019-02201-x", 
        "inLanguage": "en", 
        "isAccessibleForFree": false, 
        "isFundedItemOf": [
          {
            "id": "sg:grant.8156059", 
            "type": "MonetaryGrant"
          }
        ], 
        "isPartOf": [
          {
            "id": "sg:journal.1297453", 
            "issn": [
              "0178-515X", 
              "1432-0797"
            ], 
            "name": "Bioprocess and Biosystems Engineering", 
            "publisher": "Springer Nature", 
            "type": "Periodical"
          }, 
          {
            "issueNumber": "1", 
            "type": "PublicationIssue"
          }, 
          {
            "type": "PublicationVolume", 
            "volumeNumber": "43"
          }
        ], 
        "keywords": [
          "asymmetric synthesis", 
          "carbonyl reductase", 
          "situ cofactor regeneration", 
          "co-immobilization strategy", 
          "key chiral", 
          "excellent activity", 
          "asymmetric biosynthesis", 
          "high enantioselectivity", 
          "side chains", 
          "batch reactions", 
          "cofactor regeneration", 
          "biocatalyst", 
          "activity recovery", 
          "chloro", 
          "extra addition", 
          "synthesis", 
          "industrial applications", 
          "NADH/NADPH", 
          "reductase", 
          "enantioselectivity", 
          "chiral", 
          "present work", 
          "specific activity", 
          "reaction", 
          "total yield", 
          "dihydroxyhexanoate", 
          "chain", 
          "yield", 
          "cofactor", 
          "biosynthesis", 
          "CDHH", 
          "NADPH", 
          "activity", 
          "SCR", 
          "potential", 
          "applications", 
          "high cost", 
          "recovery", 
          "addition", 
          "cycle", 
          "work", 
          "regeneration", 
          "strategies", 
          "study", 
          "rosuvastatin", 
          "cost", 
          "requirements", 
          "Abstracttert-Butyl", 
          "lipid-lowering drug rosuvastatin", 
          "drug rosuvastatin", 
          "cofactor NADH/NADPH", 
          "self-sufficient biocatalyst", 
          "amino resin carrier LX-1000HAA", 
          "resin carrier LX-1000HAA", 
          "carrier LX-1000HAA", 
          "LX-1000HAA", 
          "Graphic abstract Asymmetric synthesis", 
          "abstract Asymmetric synthesis"
        ], 
        "name": "Asymmetric synthesis of tert-butyl (3R,5S)-6-chloro-3,5-dihydroxyhexanoate using a self-sufficient biocatalyst based on carbonyl reductase and cofactor co-immobilization", 
        "pagination": "21-31", 
        "productId": [
          {
            "name": "dimensions_id", 
            "type": "PropertyValue", 
            "value": [
              "pub.1121176127"
            ]
          }, 
          {
            "name": "doi", 
            "type": "PropertyValue", 
            "value": [
              "10.1007/s00449-019-02201-x"
            ]
          }, 
          {
            "name": "pubmed_id", 
            "type": "PropertyValue", 
            "value": [
              "31542820"
            ]
          }
        ], 
        "sameAs": [
          "https://doi.org/10.1007/s00449-019-02201-x", 
          "https://app.dimensions.ai/details/publication/pub.1121176127"
        ], 
        "sdDataset": "articles", 
        "sdDatePublished": "2022-01-01T18:52", 
        "sdLicense": "https://scigraph.springernature.com/explorer/license/", 
        "sdPublisher": {
          "name": "Springer Nature - SN SciGraph project", 
          "type": "Organization"
        }, 
        "sdSource": "s3://com-springernature-scigraph/baseset/20220101/entities/gbq_results/article/article_801.jsonl", 
        "type": "ScholarlyArticle", 
        "url": "https://doi.org/10.1007/s00449-019-02201-x"
      }
    ]
     

    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.10.1007/s00449-019-02201-x'

    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/s00449-019-02201-x'

    Turtle is a human-readable linked data format.

    curl -H 'Accept: text/turtle' 'https://scigraph.springernature.com/pub.10.1007/s00449-019-02201-x'

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

    curl -H 'Accept: application/rdf+xml' 'https://scigraph.springernature.com/pub.10.1007/s00449-019-02201-x'


     

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

    254 TRIPLES      22 PREDICATES      110 URIs      85 LITERALS      16 BLANK NODES

    Subject Predicate Object
    1 sg:pub.10.1007/s00449-019-02201-x schema:about N108fffbfcfb64d0496bc2b4c9c944d02
    2 N4c5047e75ae74ffcaef92973efd72722
    3 N5ba0b27dfb334c33bb0588d771eb4648
    4 N687f66cb062b40bf96e0fb36ed3523a9
    5 N70bdf9901f6a4a88b2cff6c3365bcbde
    6 N72fce64d333344ac8132f0d7f0450a9e
    7 N8d0da468562f4a0087b8c765ca2fa9cc
    8 Nc4810049fee84427b703191c7e5929a3
    9 Nf3bd8969dead4a29a0bd13e06ece6163
    10 anzsrc-for:09
    11 anzsrc-for:0903
    12 anzsrc-for:0904
    13 anzsrc-for:10
    14 anzsrc-for:1003
    15 schema:author N02a5c5aa6b6742c78fa98125cbc3b6c6
    16 schema:citation sg:pub.10.1007/s00253-004-1837-6
    17 sg:pub.10.1007/s00253-005-1921-6
    18 sg:pub.10.1007/s00253-015-6675-1
    19 sg:pub.10.1007/s00253-016-8083-6
    20 sg:pub.10.1007/s00253-017-8556-2
    21 sg:pub.10.1007/s00449-008-0205-9
    22 sg:pub.10.1007/s00449-014-1202-9
    23 sg:pub.10.1007/s10529-017-2415-1
    24 sg:pub.10.1007/s11814-012-0093-1
    25 sg:pub.10.1007/s12010-018-2904-2
    26 sg:pub.10.1038/227680a0
    27 sg:pub.10.1038/s41570-017-0016
    28 sg:pub.10.1038/s41598-017-03168-z
    29 sg:pub.10.1186/s12934-016-0585-5
    30 schema:datePublished 2019-09-21
    31 schema:datePublishedReg 2019-09-21
    32 schema:description Abstracttert-Butyl (3R,5S)-6-chloro-3,5-dihydroxyhexanoate [(3R,5S)-CDHH] is the key chiral intermediate to synthesize the side chain of the lipid-lowering drug rosuvastatin. Carbonyl reductases showed excellent activity for the biosynthesis of (3R,5S)-CDHH. The requirement of cofactor NADH/NADPH leads to high cost for the industrial application of carbonyl reductases. In this study, a self-sufficient biocatalyst based on carbonyl reductase and NADP+ co-immobilization strategy was developed on an amino resin carrier LX-1000HAA (SCR-NADP+@LX-1000HAA). The self-sufficient biocatalyst achieved in situ cofactor regeneration and showed the activity recovery of 77.93% and the specific activity of 70.45 U/g. Asymmetric synthesis of (3R,5S)-CDHH using SCR-NADP+@LX-1000HAA showed high enantioselectivity (> 99% e.e.) and yield (98.54%). Batch reactions were performed for ten cycles without extra addition of NADP+, and the total yield of (3R,5S)-CDHH achieved at 10.56 g/g biocatalyst. The present work demonstrated the potential of the self-sufficient biocatalyst for the asymmetric biosynthesis of rosuvastatin intermediate.Graphic abstract
    33 schema:genre article
    34 schema:inLanguage en
    35 schema:isAccessibleForFree false
    36 schema:isPartOf N388cfffa0b4c442c802a05c311d59b23
    37 Nd9cc55f199c04daa910491c271114312
    38 sg:journal.1297453
    39 schema:keywords Abstracttert-Butyl
    40 CDHH
    41 Graphic abstract Asymmetric synthesis
    42 LX-1000HAA
    43 NADH/NADPH
    44 NADPH
    45 SCR
    46 abstract Asymmetric synthesis
    47 activity
    48 activity recovery
    49 addition
    50 amino resin carrier LX-1000HAA
    51 applications
    52 asymmetric biosynthesis
    53 asymmetric synthesis
    54 batch reactions
    55 biocatalyst
    56 biosynthesis
    57 carbonyl reductase
    58 carrier LX-1000HAA
    59 chain
    60 chiral
    61 chloro
    62 co-immobilization strategy
    63 cofactor
    64 cofactor NADH/NADPH
    65 cofactor regeneration
    66 cost
    67 cycle
    68 dihydroxyhexanoate
    69 drug rosuvastatin
    70 enantioselectivity
    71 excellent activity
    72 extra addition
    73 high cost
    74 high enantioselectivity
    75 industrial applications
    76 key chiral
    77 lipid-lowering drug rosuvastatin
    78 potential
    79 present work
    80 reaction
    81 recovery
    82 reductase
    83 regeneration
    84 requirements
    85 resin carrier LX-1000HAA
    86 rosuvastatin
    87 self-sufficient biocatalyst
    88 side chains
    89 situ cofactor regeneration
    90 specific activity
    91 strategies
    92 study
    93 synthesis
    94 total yield
    95 work
    96 yield
    97 schema:name Asymmetric synthesis of tert-butyl (3R,5S)-6-chloro-3,5-dihydroxyhexanoate using a self-sufficient biocatalyst based on carbonyl reductase and cofactor co-immobilization
    98 schema:pagination 21-31
    99 schema:productId N74af187d77fb4663a219724147e3b94f
    100 Nb01c59c634f54edcaa08d71f26139203
    101 Nd623148d859742b39e5a05522fe64256
    102 schema:sameAs https://app.dimensions.ai/details/publication/pub.1121176127
    103 https://doi.org/10.1007/s00449-019-02201-x
    104 schema:sdDatePublished 2022-01-01T18:52
    105 schema:sdLicense https://scigraph.springernature.com/explorer/license/
    106 schema:sdPublisher N689cc818511540eba12aee13ae050b1e
    107 schema:url https://doi.org/10.1007/s00449-019-02201-x
    108 sgo:license sg:explorer/license/
    109 sgo:sdDataset articles
    110 rdf:type schema:ScholarlyArticle
    111 N02a5c5aa6b6742c78fa98125cbc3b6c6 rdf:first sg:person.015254304653.17
    112 rdf:rest N496950e0ef7a499e923f61049176a837
    113 N108fffbfcfb64d0496bc2b4c9c944d02 schema:inDefinedTermSet https://www.nlm.nih.gov/mesh/
    114 schema:name NADP
    115 rdf:type schema:DefinedTerm
    116 N388cfffa0b4c442c802a05c311d59b23 schema:volumeNumber 43
    117 rdf:type schema:PublicationVolume
    118 N496950e0ef7a499e923f61049176a837 rdf:first sg:person.013506337743.10
    119 rdf:rest Nc712f5814428493093b54751bf951447
    120 N4c5047e75ae74ffcaef92973efd72722 schema:inDefinedTermSet https://www.nlm.nih.gov/mesh/
    121 schema:name Alcohol Oxidoreductases
    122 rdf:type schema:DefinedTerm
    123 N5ba0b27dfb334c33bb0588d771eb4648 schema:inDefinedTermSet https://www.nlm.nih.gov/mesh/
    124 schema:name Recombinant Proteins
    125 rdf:type schema:DefinedTerm
    126 N687f66cb062b40bf96e0fb36ed3523a9 schema:inDefinedTermSet https://www.nlm.nih.gov/mesh/
    127 schema:name Rosuvastatin Calcium
    128 rdf:type schema:DefinedTerm
    129 N689cc818511540eba12aee13ae050b1e schema:name Springer Nature - SN SciGraph project
    130 rdf:type schema:Organization
    131 N70bdf9901f6a4a88b2cff6c3365bcbde schema:inDefinedTermSet https://www.nlm.nih.gov/mesh/
    132 schema:name Caproates
    133 rdf:type schema:DefinedTerm
    134 N72fce64d333344ac8132f0d7f0450a9e schema:inDefinedTermSet https://www.nlm.nih.gov/mesh/
    135 schema:name Enzymes, Immobilized
    136 rdf:type schema:DefinedTerm
    137 N74af187d77fb4663a219724147e3b94f schema:name doi
    138 schema:value 10.1007/s00449-019-02201-x
    139 rdf:type schema:PropertyValue
    140 N8d0da468562f4a0087b8c765ca2fa9cc schema:inDefinedTermSet https://www.nlm.nih.gov/mesh/
    141 schema:name Biocatalysis
    142 rdf:type schema:DefinedTerm
    143 Nb01c59c634f54edcaa08d71f26139203 schema:name pubmed_id
    144 schema:value 31542820
    145 rdf:type schema:PropertyValue
    146 Nc4810049fee84427b703191c7e5929a3 schema:inDefinedTermSet https://www.nlm.nih.gov/mesh/
    147 schema:name Fungal Proteins
    148 rdf:type schema:DefinedTerm
    149 Nc712f5814428493093b54751bf951447 rdf:first sg:person.010602155114.51
    150 rdf:rest Nc998c46ae79143348b7f7bddd6fc6558
    151 Nc998c46ae79143348b7f7bddd6fc6558 rdf:first sg:person.01256734541.85
    152 rdf:rest Nd0821490d35b42b08ee87903a225a130
    153 Nd0821490d35b42b08ee87903a225a130 rdf:first sg:person.01144225405.06
    154 rdf:rest rdf:nil
    155 Nd623148d859742b39e5a05522fe64256 schema:name dimensions_id
    156 schema:value pub.1121176127
    157 rdf:type schema:PropertyValue
    158 Nd9cc55f199c04daa910491c271114312 schema:issueNumber 1
    159 rdf:type schema:PublicationIssue
    160 Nf3bd8969dead4a29a0bd13e06ece6163 schema:inDefinedTermSet https://www.nlm.nih.gov/mesh/
    161 schema:name Candida
    162 rdf:type schema:DefinedTerm
    163 anzsrc-for:09 schema:inDefinedTermSet anzsrc-for:
    164 schema:name Engineering
    165 rdf:type schema:DefinedTerm
    166 anzsrc-for:0903 schema:inDefinedTermSet anzsrc-for:
    167 schema:name Biomedical Engineering
    168 rdf:type schema:DefinedTerm
    169 anzsrc-for:0904 schema:inDefinedTermSet anzsrc-for:
    170 schema:name Chemical Engineering
    171 rdf:type schema:DefinedTerm
    172 anzsrc-for:10 schema:inDefinedTermSet anzsrc-for:
    173 schema:name Technology
    174 rdf:type schema:DefinedTerm
    175 anzsrc-for:1003 schema:inDefinedTermSet anzsrc-for:
    176 schema:name Industrial Biotechnology
    177 rdf:type schema:DefinedTerm
    178 sg:grant.8156059 http://pending.schema.org/fundedItem sg:pub.10.1007/s00449-019-02201-x
    179 rdf:type schema:MonetaryGrant
    180 sg:journal.1297453 schema:issn 0178-515X
    181 1432-0797
    182 schema:name Bioprocess and Biosystems Engineering
    183 schema:publisher Springer Nature
    184 rdf:type schema:Periodical
    185 sg:person.010602155114.51 schema:affiliation grid-institutes:grid.469325.f
    186 schema:familyName Zhou
    187 schema:givenName Rong
    188 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.010602155114.51
    189 rdf:type schema:Person
    190 sg:person.01144225405.06 schema:affiliation grid-institutes:grid.469325.f
    191 schema:familyName Zheng
    192 schema:givenName Yu-Guo
    193 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01144225405.06
    194 rdf:type schema:Person
    195 sg:person.01256734541.85 schema:affiliation grid-institutes:grid.469325.f
    196 schema:familyName Liu
    197 schema:givenName Zhi-Qiang
    198 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01256734541.85
    199 rdf:type schema:Person
    200 sg:person.013506337743.10 schema:affiliation grid-institutes:grid.469325.f
    201 schema:familyName Wang
    202 schema:givenName Wen-Zhong
    203 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.013506337743.10
    204 rdf:type schema:Person
    205 sg:person.015254304653.17 schema:affiliation grid-institutes:grid.469325.f
    206 schema:familyName Zhang
    207 schema:givenName Xiao-Jian
    208 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.015254304653.17
    209 rdf:type schema:Person
    210 sg:pub.10.1007/s00253-004-1837-6 schema:sameAs https://app.dimensions.ai/details/publication/pub.1037870387
    211 https://doi.org/10.1007/s00253-004-1837-6
    212 rdf:type schema:CreativeWork
    213 sg:pub.10.1007/s00253-005-1921-6 schema:sameAs https://app.dimensions.ai/details/publication/pub.1005725582
    214 https://doi.org/10.1007/s00253-005-1921-6
    215 rdf:type schema:CreativeWork
    216 sg:pub.10.1007/s00253-015-6675-1 schema:sameAs https://app.dimensions.ai/details/publication/pub.1040837053
    217 https://doi.org/10.1007/s00253-015-6675-1
    218 rdf:type schema:CreativeWork
    219 sg:pub.10.1007/s00253-016-8083-6 schema:sameAs https://app.dimensions.ai/details/publication/pub.1050459052
    220 https://doi.org/10.1007/s00253-016-8083-6
    221 rdf:type schema:CreativeWork
    222 sg:pub.10.1007/s00253-017-8556-2 schema:sameAs https://app.dimensions.ai/details/publication/pub.1092340057
    223 https://doi.org/10.1007/s00253-017-8556-2
    224 rdf:type schema:CreativeWork
    225 sg:pub.10.1007/s00449-008-0205-9 schema:sameAs https://app.dimensions.ai/details/publication/pub.1050406645
    226 https://doi.org/10.1007/s00449-008-0205-9
    227 rdf:type schema:CreativeWork
    228 sg:pub.10.1007/s00449-014-1202-9 schema:sameAs https://app.dimensions.ai/details/publication/pub.1037510106
    229 https://doi.org/10.1007/s00449-014-1202-9
    230 rdf:type schema:CreativeWork
    231 sg:pub.10.1007/s10529-017-2415-1 schema:sameAs https://app.dimensions.ai/details/publication/pub.1091284948
    232 https://doi.org/10.1007/s10529-017-2415-1
    233 rdf:type schema:CreativeWork
    234 sg:pub.10.1007/s11814-012-0093-1 schema:sameAs https://app.dimensions.ai/details/publication/pub.1009746025
    235 https://doi.org/10.1007/s11814-012-0093-1
    236 rdf:type schema:CreativeWork
    237 sg:pub.10.1007/s12010-018-2904-2 schema:sameAs https://app.dimensions.ai/details/publication/pub.1107728294
    238 https://doi.org/10.1007/s12010-018-2904-2
    239 rdf:type schema:CreativeWork
    240 sg:pub.10.1038/227680a0 schema:sameAs https://app.dimensions.ai/details/publication/pub.1010419937
    241 https://doi.org/10.1038/227680a0
    242 rdf:type schema:CreativeWork
    243 sg:pub.10.1038/s41570-017-0016 schema:sameAs https://app.dimensions.ai/details/publication/pub.1083742827
    244 https://doi.org/10.1038/s41570-017-0016
    245 rdf:type schema:CreativeWork
    246 sg:pub.10.1038/s41598-017-03168-z schema:sameAs https://app.dimensions.ai/details/publication/pub.1085846261
    247 https://doi.org/10.1038/s41598-017-03168-z
    248 rdf:type schema:CreativeWork
    249 sg:pub.10.1186/s12934-016-0585-5 schema:sameAs https://app.dimensions.ai/details/publication/pub.1034558571
    250 https://doi.org/10.1186/s12934-016-0585-5
    251 rdf:type schema:CreativeWork
    252 grid-institutes:grid.469325.f schema:alternateName Key Laboratory of Bioorganic Synthesis of Zhejiang Province, College of Biotechnology and Bioengineering, Zhejiang University of Technology, 310014, Hangzhou, China
    253 schema:name Key Laboratory of Bioorganic Synthesis of Zhejiang Province, College of Biotechnology and Bioengineering, Zhejiang University of Technology, 310014, Hangzhou, China
    254 rdf:type schema:Organization
     




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


    ...