Enantioseparation of mandelic acid on vancomycin column: Experimental and docking study
So far, no detailed view has been expressed regarding the interactions between vancomycin and racemic compounds including mandelic acid. In the current study, a chiral stationary phase was prepared by using 3‐aminopropyltriethoxysilane and succinic anhydride to graft carboxylated silica microspheres...
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| Veröffentlicht in: | Chirality (New York, N.Y.) N.Y.), 2020-11, Vol.32 (11), p.1289-1298 |
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| creator | Shahnani, Mostafa Sefidbakht, Yahya Maghari, Shokoofeh Mehdi, Ahmad Rezadoost, Hassan Ghassempour, Alireza |
| description | So far, no detailed view has been expressed regarding the interactions between vancomycin and racemic compounds including mandelic acid. In the current study, a chiral stationary phase was prepared by using 3‐aminopropyltriethoxysilane and succinic anhydride to graft carboxylated silica microspheres and subsequently by activating the carboxylic acid group for vancomycin immobilization. Characterization by elemental analysis, Fourier transform infrared spectroscopy, solid‐state nuclear magnetic resonance, and thermogravimetric analysis demonstrated effective functionalization of the silica surface. R and S enantiomers of mandelic acid were separated by the synthetic vancomycin column. Finally, the interaction between vancomycin and R/S mandelic acid enantiomers was simulated by Auto‐dock Vina. The binding energies of interactions between R and S enantiomers and vancomycin chiral stationary phase were different. In the most probable interaction, the difference in mandelic acid binding energy was approximately 0.2 kcal/mol. In addition, circular dichroism spectra of vancomycin interacting with R and S enantiomers showed different patterns. Therefore, R and S mandelic acid enantiomers may occupy various binding pockets and interact with different vancomycin functions. These observations emphasized the different retention of R and S mandelic acid enantiomers in vancomycin chiral column. |
| doi_str_mv | 10.1002/chir.23273 |
| format | Article |
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In the current study, a chiral stationary phase was prepared by using 3‐aminopropyltriethoxysilane and succinic anhydride to graft carboxylated silica microspheres and subsequently by activating the carboxylic acid group for vancomycin immobilization. Characterization by elemental analysis, Fourier transform infrared spectroscopy, solid‐state nuclear magnetic resonance, and thermogravimetric analysis demonstrated effective functionalization of the silica surface. R and S enantiomers of mandelic acid were separated by the synthetic vancomycin column. Finally, the interaction between vancomycin and R/S mandelic acid enantiomers was simulated by Auto‐dock Vina. The binding energies of interactions between R and S enantiomers and vancomycin chiral stationary phase were different. In the most probable interaction, the difference in mandelic acid binding energy was approximately 0.2 kcal/mol. In addition, circular dichroism spectra of vancomycin interacting with R and S enantiomers showed different patterns. Therefore, R and S mandelic acid enantiomers may occupy various binding pockets and interact with different vancomycin functions. These observations emphasized the different retention of R and S mandelic acid enantiomers in vancomycin chiral column.</description><identifier>ISSN: 0899-0042</identifier><identifier>EISSN: 1520-636X</identifier><identifier>DOI: 10.1002/chir.23273</identifier><identifier>PMID: 32797693</identifier><language>eng</language><publisher>HOBOKEN: Wiley</publisher><subject>Acids ; Aminopropyltriethoxysilane ; Binding energy ; Carboxylic acids ; Chemical Sciences ; Chemistry ; Chemistry, Analytical ; Chemistry, Medicinal ; Chemistry, Organic ; chiral mechanisms ; Circular dichroism ; Column chromatography ; Dichroism ; docking and CD analysis ; Enantiomers ; Fourier analysis ; Fourier transforms ; Immobilization ; Infrared analysis ; Infrared spectroscopy ; Life Sciences & Biomedicine ; mandelic acid enantiomers ; Material chemistry ; Microspheres ; NMR ; Nuclear magnetic resonance ; Pharmacology & Pharmacy ; Physical Sciences ; Science & Technology ; Silica ; Silicon dioxide ; Spectrum analysis ; Stationary phase ; Thermogravimetric analysis ; Vancomycin ; vancomycin stationary phase</subject><ispartof>Chirality (New York, N.Y.), 2020-11, Vol.32 (11), p.1289-1298</ispartof><rights>2020 Wiley Periodicals LLC.</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>true</woscitedreferencessubscribed><woscitedreferencescount>14</woscitedreferencescount><woscitedreferencesoriginalsourcerecordid>wos000559497800001</woscitedreferencesoriginalsourcerecordid><citedby>FETCH-LOGICAL-c3683-f1186a8dc00ba50a03fefc1d0f402a6021cac8bbba89b24a2044ce660bf8c1553</citedby><cites>FETCH-LOGICAL-c3683-f1186a8dc00ba50a03fefc1d0f402a6021cac8bbba89b24a2044ce660bf8c1553</cites><orcidid>0000-0002-6845-6034 ; 0000-0002-6435-9915 ; 0000-0003-0538-0252 ; 0000-0002-7545-2488 ; 0000-0002-7830-2012</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fchir.23273$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchir.23273$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>230,315,781,785,886,1418,27929,27930,28253,45579,45580</link.rule.ids><backlink>$$Uhttps://hal.science/hal-02962227$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Shahnani, Mostafa</creatorcontrib><creatorcontrib>Sefidbakht, Yahya</creatorcontrib><creatorcontrib>Maghari, Shokoofeh</creatorcontrib><creatorcontrib>Mehdi, Ahmad</creatorcontrib><creatorcontrib>Rezadoost, Hassan</creatorcontrib><creatorcontrib>Ghassempour, Alireza</creatorcontrib><title>Enantioseparation of mandelic acid on vancomycin column: Experimental and docking study</title><title>Chirality (New York, N.Y.)</title><addtitle>CHIRALITY</addtitle><description>So far, no detailed view has been expressed regarding the interactions between vancomycin and racemic compounds including mandelic acid. In the current study, a chiral stationary phase was prepared by using 3‐aminopropyltriethoxysilane and succinic anhydride to graft carboxylated silica microspheres and subsequently by activating the carboxylic acid group for vancomycin immobilization. Characterization by elemental analysis, Fourier transform infrared spectroscopy, solid‐state nuclear magnetic resonance, and thermogravimetric analysis demonstrated effective functionalization of the silica surface. R and S enantiomers of mandelic acid were separated by the synthetic vancomycin column. Finally, the interaction between vancomycin and R/S mandelic acid enantiomers was simulated by Auto‐dock Vina. The binding energies of interactions between R and S enantiomers and vancomycin chiral stationary phase were different. In the most probable interaction, the difference in mandelic acid binding energy was approximately 0.2 kcal/mol. In addition, circular dichroism spectra of vancomycin interacting with R and S enantiomers showed different patterns. Therefore, R and S mandelic acid enantiomers may occupy various binding pockets and interact with different vancomycin functions. These observations emphasized the different retention of R and S mandelic acid enantiomers in vancomycin chiral column.</description><subject>Acids</subject><subject>Aminopropyltriethoxysilane</subject><subject>Binding energy</subject><subject>Carboxylic acids</subject><subject>Chemical Sciences</subject><subject>Chemistry</subject><subject>Chemistry, Analytical</subject><subject>Chemistry, Medicinal</subject><subject>Chemistry, Organic</subject><subject>chiral mechanisms</subject><subject>Circular dichroism</subject><subject>Column chromatography</subject><subject>Dichroism</subject><subject>docking and CD analysis</subject><subject>Enantiomers</subject><subject>Fourier analysis</subject><subject>Fourier transforms</subject><subject>Immobilization</subject><subject>Infrared analysis</subject><subject>Infrared spectroscopy</subject><subject>Life Sciences & Biomedicine</subject><subject>mandelic acid enantiomers</subject><subject>Material chemistry</subject><subject>Microspheres</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Pharmacology & Pharmacy</subject><subject>Physical Sciences</subject><subject>Science & Technology</subject><subject>Silica</subject><subject>Silicon dioxide</subject><subject>Spectrum analysis</subject><subject>Stationary phase</subject><subject>Thermogravimetric analysis</subject><subject>Vancomycin</subject><subject>vancomycin stationary phase</subject><issn>0899-0042</issn><issn>1520-636X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>AOWDO</sourceid><recordid>eNqNkU2LFDEQhoMo7rh68RcEPKn0WvnoTMfb0ozOwoAgit5CdTpxs_YkY6d7df69me1lj-IpRfG8xcMbQl4yuGAA_J29DuMFF3wtHpEVqzlUSqjvj8kKGq0rAMnPyLOcbwBAKyGfkrPC6rXSYkW-bSLGKaTsDjhiGSJNnu4x9m4IlqINPS27W4w27Y82RGrTMO_je7r5c3Bj2Ls44UALT_tkf4b4g-Zp7o_PyROPQ3Yv7t9z8vXD5ku7rXafPl61l7vKCtWIyjPWKGx6C9BhDQjCO29ZD14CRwWcWbRN13XY6I5L5CCldUpB5xvL6lqck9fL3WsczKH44Hg0CYPZXu7MaQdcK875-pYV9tXCHsb0a3Z5MjdpHmPRM1xKzVUtlSrUm4WyY8p5dP7hLANz6tuc-jZ3fRf47QL_dl3y2QYXrXsIlMLrWku9bsoEJ4Hm_-k2THf_0aY5TiXK7qNhcMd_KJl2e_V5kfsLfbGhhw</recordid><startdate>202011</startdate><enddate>202011</enddate><creator>Shahnani, Mostafa</creator><creator>Sefidbakht, Yahya</creator><creator>Maghari, Shokoofeh</creator><creator>Mehdi, Ahmad</creator><creator>Rezadoost, Hassan</creator><creator>Ghassempour, Alireza</creator><general>Wiley</general><general>Wiley Subscription Services, Inc</general><scope>AOWDO</scope><scope>BLEPL</scope><scope>DTL</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7QR</scope><scope>7U7</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>1XC</scope><orcidid>https://orcid.org/0000-0002-6845-6034</orcidid><orcidid>https://orcid.org/0000-0002-6435-9915</orcidid><orcidid>https://orcid.org/0000-0003-0538-0252</orcidid><orcidid>https://orcid.org/0000-0002-7545-2488</orcidid><orcidid>https://orcid.org/0000-0002-7830-2012</orcidid></search><sort><creationdate>202011</creationdate><title>Enantioseparation of mandelic acid on vancomycin column: Experimental and docking study</title><author>Shahnani, Mostafa ; Sefidbakht, Yahya ; Maghari, Shokoofeh ; Mehdi, Ahmad ; Rezadoost, Hassan ; Ghassempour, Alireza</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3683-f1186a8dc00ba50a03fefc1d0f402a6021cac8bbba89b24a2044ce660bf8c1553</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Acids</topic><topic>Aminopropyltriethoxysilane</topic><topic>Binding energy</topic><topic>Carboxylic acids</topic><topic>Chemical Sciences</topic><topic>Chemistry</topic><topic>Chemistry, Analytical</topic><topic>Chemistry, Medicinal</topic><topic>Chemistry, Organic</topic><topic>chiral mechanisms</topic><topic>Circular dichroism</topic><topic>Column chromatography</topic><topic>Dichroism</topic><topic>docking and CD analysis</topic><topic>Enantiomers</topic><topic>Fourier analysis</topic><topic>Fourier transforms</topic><topic>Immobilization</topic><topic>Infrared analysis</topic><topic>Infrared spectroscopy</topic><topic>Life Sciences & Biomedicine</topic><topic>mandelic acid enantiomers</topic><topic>Material chemistry</topic><topic>Microspheres</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Pharmacology & Pharmacy</topic><topic>Physical Sciences</topic><topic>Science & Technology</topic><topic>Silica</topic><topic>Silicon dioxide</topic><topic>Spectrum analysis</topic><topic>Stationary phase</topic><topic>Thermogravimetric analysis</topic><topic>Vancomycin</topic><topic>vancomycin stationary phase</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Shahnani, Mostafa</creatorcontrib><creatorcontrib>Sefidbakht, Yahya</creatorcontrib><creatorcontrib>Maghari, Shokoofeh</creatorcontrib><creatorcontrib>Mehdi, Ahmad</creatorcontrib><creatorcontrib>Rezadoost, Hassan</creatorcontrib><creatorcontrib>Ghassempour, Alireza</creatorcontrib><collection>Web of Science - Science Citation Index Expanded - 2020</collection><collection>Web of Science Core Collection</collection><collection>Science Citation Index Expanded</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Chemoreception Abstracts</collection><collection>Toxicology Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>Hyper Article en Ligne (HAL)</collection><jtitle>Chirality (New York, N.Y.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Shahnani, Mostafa</au><au>Sefidbakht, Yahya</au><au>Maghari, Shokoofeh</au><au>Mehdi, Ahmad</au><au>Rezadoost, Hassan</au><au>Ghassempour, Alireza</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enantioseparation of mandelic acid on vancomycin column: Experimental and docking study</atitle><jtitle>Chirality (New York, N.Y.)</jtitle><stitle>CHIRALITY</stitle><date>2020-11</date><risdate>2020</risdate><volume>32</volume><issue>11</issue><spage>1289</spage><epage>1298</epage><pages>1289-1298</pages><issn>0899-0042</issn><eissn>1520-636X</eissn><abstract>So far, no detailed view has been expressed regarding the interactions between vancomycin and racemic compounds including mandelic acid. In the current study, a chiral stationary phase was prepared by using 3‐aminopropyltriethoxysilane and succinic anhydride to graft carboxylated silica microspheres and subsequently by activating the carboxylic acid group for vancomycin immobilization. Characterization by elemental analysis, Fourier transform infrared spectroscopy, solid‐state nuclear magnetic resonance, and thermogravimetric analysis demonstrated effective functionalization of the silica surface. R and S enantiomers of mandelic acid were separated by the synthetic vancomycin column. Finally, the interaction between vancomycin and R/S mandelic acid enantiomers was simulated by Auto‐dock Vina. The binding energies of interactions between R and S enantiomers and vancomycin chiral stationary phase were different. In the most probable interaction, the difference in mandelic acid binding energy was approximately 0.2 kcal/mol. In addition, circular dichroism spectra of vancomycin interacting with R and S enantiomers showed different patterns. Therefore, R and S mandelic acid enantiomers may occupy various binding pockets and interact with different vancomycin functions. These observations emphasized the different retention of R and S mandelic acid enantiomers in vancomycin chiral column.</abstract><cop>HOBOKEN</cop><pub>Wiley</pub><pmid>32797693</pmid><doi>10.1002/chir.23273</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0002-6845-6034</orcidid><orcidid>https://orcid.org/0000-0002-6435-9915</orcidid><orcidid>https://orcid.org/0000-0003-0538-0252</orcidid><orcidid>https://orcid.org/0000-0002-7545-2488</orcidid><orcidid>https://orcid.org/0000-0002-7830-2012</orcidid></addata></record> |
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| subjects | Acids Aminopropyltriethoxysilane Binding energy Carboxylic acids Chemical Sciences Chemistry Chemistry, Analytical Chemistry, Medicinal Chemistry, Organic chiral mechanisms Circular dichroism Column chromatography Dichroism docking and CD analysis Enantiomers Fourier analysis Fourier transforms Immobilization Infrared analysis Infrared spectroscopy Life Sciences & Biomedicine mandelic acid enantiomers Material chemistry Microspheres NMR Nuclear magnetic resonance Pharmacology & Pharmacy Physical Sciences Science & Technology Silica Silicon dioxide Spectrum analysis Stationary phase Thermogravimetric analysis Vancomycin vancomycin stationary phase |
| title | Enantioseparation of mandelic acid on vancomycin column: Experimental and docking study |
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