Hydrogen-Bonding-Driven Enantioselective Resolution against the Kazlauskas Rule To Afford γ-Amino Alcohols by Candida rugosa Lipase
Most lipases resolve secondary alcohols in accordance with the “Kazlauskas rule” to give the R enantiomers. In a similar manner to other lipases, Candida rugosa lipase (CRL) exhibits R enantioselectivity towards heptan‐2‐ol, although the enantiomeric ratio (E) is low (E=1.6). However, unexpected ena...
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| Veröffentlicht in: | Chembiochem : a European journal of chemical biology 2015-01, Vol.16 (1), p.77-82 |
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| creator | Min, Bora Park, Jeemin Sim, Yong-Kyun Jung, Suhyun Kim, Seong-Ho Song, Jae Kwang Kim, Bum Tae Park, Sang Youn Yun, Jaesook Park, Seongsoon Lee, Hyuk |
| description | Most lipases resolve secondary alcohols in accordance with the “Kazlauskas rule” to give the R enantiomers. In a similar manner to other lipases, Candida rugosa lipase (CRL) exhibits R enantioselectivity towards heptan‐2‐ol, although the enantiomeric ratio (E) is low (E=1.6). However, unexpected enantioselectivity (i.e., S enantioselectivity, E=58) of CRL towards 4‐(tert‐butoxycarbonylamino)butan‐2‐ol, which has a similar chain length to heptan‐2‐ol, has been observed. To develop a deeper understanding of the molecular basis for this unusual enantioselectivity, we have conducted a series of molecular modeling and substrate engineering experiments. The results of these computational and experimental analyses indicated that a hydrogen bond between the Ser450 residue and the nitrogen atom of the carbamate group is critical to stabilize the transition state of the S enantiomer.
Enantioselectivity reversal: Candida rugosa lipase (CRL) exhibits unexpected enantioselectivity (i.e., S selectivity, E=58) towards 4‐(tert‐butoxycarbonylamino)butan‐2‐ol. A molecular modeling study suggests that the formation of a hydrogen bond between the Ser450 residue and the carbamate nitrogen atom is essential for the observed selectivity. |
| doi_str_mv | 10.1002/cbic.201402563 |
| format | Article |
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Enantioselectivity reversal: Candida rugosa lipase (CRL) exhibits unexpected enantioselectivity (i.e., S selectivity, E=58) towards 4‐(tert‐butoxycarbonylamino)butan‐2‐ol. A molecular modeling study suggests that the formation of a hydrogen bond between the Ser450 residue and the carbamate nitrogen atom is essential for the observed selectivity.</description><identifier>ISSN: 1439-4227</identifier><identifier>EISSN: 1439-7633</identifier><identifier>DOI: 10.1002/cbic.201402563</identifier><identifier>PMID: 25477295</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>amino alcohols ; Amino Alcohols - chemistry ; Candida - chemistry ; Candida - enzymology ; Candida rugosa ; Fungal Proteins - chemistry ; Heptanol - chemistry ; Hydrogen Bonding ; Kazlauskas rule ; kinetic resolution ; Kinetics ; Lipase - chemistry ; lipases ; Models, Molecular ; molecular modeling ; Recombinant Proteins - chemistry ; Stereoisomerism ; Structure-Activity Relationship ; Substrate Specificity</subject><ispartof>Chembiochem : a European journal of chemical biology, 2015-01, Vol.16 (1), p.77-82</ispartof><rights>2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4163-964128b17a43954eb25656faaac2d5e8d1bd7d2ab18d65a306e35e4f91471be33</citedby><cites>FETCH-LOGICAL-c4163-964128b17a43954eb25656faaac2d5e8d1bd7d2ab18d65a306e35e4f91471be33</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fcbic.201402563$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fcbic.201402563$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1416,27922,27923,45572,45573</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25477295$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Min, Bora</creatorcontrib><creatorcontrib>Park, Jeemin</creatorcontrib><creatorcontrib>Sim, Yong-Kyun</creatorcontrib><creatorcontrib>Jung, Suhyun</creatorcontrib><creatorcontrib>Kim, Seong-Ho</creatorcontrib><creatorcontrib>Song, Jae Kwang</creatorcontrib><creatorcontrib>Kim, Bum Tae</creatorcontrib><creatorcontrib>Park, Sang Youn</creatorcontrib><creatorcontrib>Yun, Jaesook</creatorcontrib><creatorcontrib>Park, Seongsoon</creatorcontrib><creatorcontrib>Lee, Hyuk</creatorcontrib><title>Hydrogen-Bonding-Driven Enantioselective Resolution against the Kazlauskas Rule To Afford γ-Amino Alcohols by Candida rugosa Lipase</title><title>Chembiochem : a European journal of chemical biology</title><addtitle>ChemBioChem</addtitle><description>Most lipases resolve secondary alcohols in accordance with the “Kazlauskas rule” to give the R enantiomers. In a similar manner to other lipases, Candida rugosa lipase (CRL) exhibits R enantioselectivity towards heptan‐2‐ol, although the enantiomeric ratio (E) is low (E=1.6). However, unexpected enantioselectivity (i.e., S enantioselectivity, E=58) of CRL towards 4‐(tert‐butoxycarbonylamino)butan‐2‐ol, which has a similar chain length to heptan‐2‐ol, has been observed. To develop a deeper understanding of the molecular basis for this unusual enantioselectivity, we have conducted a series of molecular modeling and substrate engineering experiments. The results of these computational and experimental analyses indicated that a hydrogen bond between the Ser450 residue and the nitrogen atom of the carbamate group is critical to stabilize the transition state of the S enantiomer.
Enantioselectivity reversal: Candida rugosa lipase (CRL) exhibits unexpected enantioselectivity (i.e., S selectivity, E=58) towards 4‐(tert‐butoxycarbonylamino)butan‐2‐ol. A molecular modeling study suggests that the formation of a hydrogen bond between the Ser450 residue and the carbamate nitrogen atom is essential for the observed selectivity.</description><subject>amino alcohols</subject><subject>Amino Alcohols - chemistry</subject><subject>Candida - chemistry</subject><subject>Candida - enzymology</subject><subject>Candida rugosa</subject><subject>Fungal Proteins - chemistry</subject><subject>Heptanol - chemistry</subject><subject>Hydrogen Bonding</subject><subject>Kazlauskas rule</subject><subject>kinetic resolution</subject><subject>Kinetics</subject><subject>Lipase - chemistry</subject><subject>lipases</subject><subject>Models, Molecular</subject><subject>molecular modeling</subject><subject>Recombinant Proteins - chemistry</subject><subject>Stereoisomerism</subject><subject>Structure-Activity Relationship</subject><subject>Substrate Specificity</subject><issn>1439-4227</issn><issn>1439-7633</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkctuEzEUhkcIREthyxJ5yWaC784s09CbiEBUQbCzzsycSU0dO7VngLDmjXgPnompEiJ2sDoXff9_dPQXxXNGJ4xS_qqpXTPhlEnKlRYPimMmRVUaLcTDfS85N0fFk5w_U0orLdjj4ograQyv1HHx43LbprjCUJ7G0LqwKl8n9wUDOQsQehczemz6cUOuMUc_jKtAYAUu5J70N0jewHcPQ76FTK4Hj2QZyazrYmrJr5_lbO3COPsm3kSfSb0lcxivtEDSsIoZyMJtIOPT4lEHPuOzfT0pPpyfLeeX5eLdxdV8tigbybQoKy0Zn9bMwPiXkliPLyvdAUDDW4XTltWtaTnUbNpqBYJqFAplVzFpWI1CnBQvd76bFO8GzL1du9yg9xAwDtkyraTWFZf6P1BJBTdaVSM62aFNijkn7OwmuTWkrWXU3odk70Oyh5BGwYu991CvsT3gf1IZgWoHfHUet_-ws_PTq_nf5uVO63KP3w5aSLdWG2GU_fj2wp4rSs2SfrLvxW-M7K6O</recordid><startdate>20150102</startdate><enddate>20150102</enddate><creator>Min, Bora</creator><creator>Park, Jeemin</creator><creator>Sim, Yong-Kyun</creator><creator>Jung, Suhyun</creator><creator>Kim, Seong-Ho</creator><creator>Song, Jae Kwang</creator><creator>Kim, Bum Tae</creator><creator>Park, Sang Youn</creator><creator>Yun, Jaesook</creator><creator>Park, Seongsoon</creator><creator>Lee, Hyuk</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>M7N</scope></search><sort><creationdate>20150102</creationdate><title>Hydrogen-Bonding-Driven Enantioselective Resolution against the Kazlauskas Rule To Afford γ-Amino Alcohols by Candida rugosa Lipase</title><author>Min, Bora ; Park, Jeemin ; Sim, Yong-Kyun ; Jung, Suhyun ; Kim, Seong-Ho ; Song, Jae Kwang ; Kim, Bum Tae ; Park, Sang Youn ; Yun, Jaesook ; Park, Seongsoon ; Lee, Hyuk</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4163-964128b17a43954eb25656faaac2d5e8d1bd7d2ab18d65a306e35e4f91471be33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>amino alcohols</topic><topic>Amino Alcohols - chemistry</topic><topic>Candida - chemistry</topic><topic>Candida - enzymology</topic><topic>Candida rugosa</topic><topic>Fungal Proteins - chemistry</topic><topic>Heptanol - chemistry</topic><topic>Hydrogen Bonding</topic><topic>Kazlauskas rule</topic><topic>kinetic resolution</topic><topic>Kinetics</topic><topic>Lipase - chemistry</topic><topic>lipases</topic><topic>Models, Molecular</topic><topic>molecular modeling</topic><topic>Recombinant Proteins - chemistry</topic><topic>Stereoisomerism</topic><topic>Structure-Activity Relationship</topic><topic>Substrate Specificity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Min, Bora</creatorcontrib><creatorcontrib>Park, Jeemin</creatorcontrib><creatorcontrib>Sim, Yong-Kyun</creatorcontrib><creatorcontrib>Jung, Suhyun</creatorcontrib><creatorcontrib>Kim, Seong-Ho</creatorcontrib><creatorcontrib>Song, Jae Kwang</creatorcontrib><creatorcontrib>Kim, Bum Tae</creatorcontrib><creatorcontrib>Park, Sang Youn</creatorcontrib><creatorcontrib>Yun, Jaesook</creatorcontrib><creatorcontrib>Park, Seongsoon</creatorcontrib><creatorcontrib>Lee, Hyuk</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><jtitle>Chembiochem : a European journal of chemical biology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Min, Bora</au><au>Park, Jeemin</au><au>Sim, Yong-Kyun</au><au>Jung, Suhyun</au><au>Kim, Seong-Ho</au><au>Song, Jae Kwang</au><au>Kim, Bum Tae</au><au>Park, Sang Youn</au><au>Yun, Jaesook</au><au>Park, Seongsoon</au><au>Lee, Hyuk</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Hydrogen-Bonding-Driven Enantioselective Resolution against the Kazlauskas Rule To Afford γ-Amino Alcohols by Candida rugosa Lipase</atitle><jtitle>Chembiochem : a European journal of chemical biology</jtitle><addtitle>ChemBioChem</addtitle><date>2015-01-02</date><risdate>2015</risdate><volume>16</volume><issue>1</issue><spage>77</spage><epage>82</epage><pages>77-82</pages><issn>1439-4227</issn><eissn>1439-7633</eissn><abstract>Most lipases resolve secondary alcohols in accordance with the “Kazlauskas rule” to give the R enantiomers. In a similar manner to other lipases, Candida rugosa lipase (CRL) exhibits R enantioselectivity towards heptan‐2‐ol, although the enantiomeric ratio (E) is low (E=1.6). However, unexpected enantioselectivity (i.e., S enantioselectivity, E=58) of CRL towards 4‐(tert‐butoxycarbonylamino)butan‐2‐ol, which has a similar chain length to heptan‐2‐ol, has been observed. To develop a deeper understanding of the molecular basis for this unusual enantioselectivity, we have conducted a series of molecular modeling and substrate engineering experiments. The results of these computational and experimental analyses indicated that a hydrogen bond between the Ser450 residue and the nitrogen atom of the carbamate group is critical to stabilize the transition state of the S enantiomer.
Enantioselectivity reversal: Candida rugosa lipase (CRL) exhibits unexpected enantioselectivity (i.e., S selectivity, E=58) towards 4‐(tert‐butoxycarbonylamino)butan‐2‐ol. A molecular modeling study suggests that the formation of a hydrogen bond between the Ser450 residue and the carbamate nitrogen atom is essential for the observed selectivity.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>25477295</pmid><doi>10.1002/cbic.201402563</doi><tpages>6</tpages></addata></record> |
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| subjects | amino alcohols Amino Alcohols - chemistry Candida - chemistry Candida - enzymology Candida rugosa Fungal Proteins - chemistry Heptanol - chemistry Hydrogen Bonding Kazlauskas rule kinetic resolution Kinetics Lipase - chemistry lipases Models, Molecular molecular modeling Recombinant Proteins - chemistry Stereoisomerism Structure-Activity Relationship Substrate Specificity |
| title | Hydrogen-Bonding-Driven Enantioselective Resolution against the Kazlauskas Rule To Afford γ-Amino Alcohols by Candida rugosa Lipase |
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