Enantioseparation of amino acid and mandelic acid enantiomers using Garphos derivatives as chiral extractants
In this paper, Garphos with different substituents were employed as chiral extractants to enantioseparate racemic amino acid and mandelic acid. The influences of metal precursors, pH of aqueous solution, Garphos‐metal concentration, extraction temperature, and substituent effect on extraction were i...
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| Veröffentlicht in: | Chirality (New York, N.Y.) N.Y.), 2022-09, Vol.34 (9), p.1239-1246 |
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| container_title | Chirality (New York, N.Y.) |
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| creator | Wang, Hou Yang, Yanning Chen, Shuhuan Xiao, Wenjie Hu, Kangyu Zhong, Changyuan Ouyang, Junying Liu, Xiong |
| description | In this paper, Garphos with different substituents were employed as chiral extractants to enantioseparate racemic amino acid and mandelic acid. The influences of metal precursors, pH of aqueous solution, Garphos‐metal concentration, extraction temperature, and substituent effect on extraction were investigated. The results indicated that the substituent groups significantly affected the π‐π interaction between extractant and substrate. And the separation factors (α) for Garphos could be remarkably improved by regulating substituent groups. Garphos‐II‐Pd, Garphos‐VI‐Pd, Garphos‐III‐Pd, Garphos‐I‐Cu, Garphos‐VI‐Cu, and Garphos‐V‐Pd were the most efficient extractants for phenylalanine (Phe), homophenylalanine (Hphe), 4‐nitrophenylalanine (Nphe), 3‐chlorophenylglycine (Cpheg), mandelic acid (MA), and 2‐chlormandelic acid (CMA) with α values of 2.40, 2.37, 5.37, 1.59, 5.98, and 3.69, respectively. This work provided an important reference for the design of efficient chiral extractants in future work. |
| doi_str_mv | 10.1002/chir.23484 |
| format | Article |
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The influences of metal precursors, pH of aqueous solution, Garphos‐metal concentration, extraction temperature, and substituent effect on extraction were investigated. The results indicated that the substituent groups significantly affected the π‐π interaction between extractant and substrate. And the separation factors (α) for Garphos could be remarkably improved by regulating substituent groups. Garphos‐II‐Pd, Garphos‐VI‐Pd, Garphos‐III‐Pd, Garphos‐I‐Cu, Garphos‐VI‐Cu, and Garphos‐V‐Pd were the most efficient extractants for phenylalanine (Phe), homophenylalanine (Hphe), 4‐nitrophenylalanine (Nphe), 3‐chlorophenylglycine (Cpheg), mandelic acid (MA), and 2‐chlormandelic acid (CMA) with α values of 2.40, 2.37, 5.37, 1.59, 5.98, and 3.69, respectively. This work provided an important reference for the design of efficient chiral extractants in future work.</description><identifier>ISSN: 0899-0042</identifier><identifier>EISSN: 1520-636X</identifier><identifier>DOI: 10.1002/chir.23484</identifier><identifier>PMID: 35689412</identifier><language>eng</language><publisher>United States: Wiley Subscription Services, Inc</publisher><subject>amino acid ; Amino acids ; Aqueous solutions ; Copper ; Enantiomers ; enantioseparation ; Extractants ; Garphos ; mandelic acid ; Metal concentrations ; Palladium ; Phenylalanine ; substituent effect ; Substrates</subject><ispartof>Chirality (New York, N.Y.), 2022-09, Vol.34 (9), p.1239-1246</ispartof><rights>2022 Wiley Periodicals LLC.</rights><rights>2022 Wiley Periodicals LLC</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c2874-96c0738e816fdc553e0b6441da483dfd9a534c5c8c5d27a289d9ceaa414d9c983</citedby><cites>FETCH-LOGICAL-c2874-96c0738e816fdc553e0b6441da483dfd9a534c5c8c5d27a289d9ceaa414d9c983</cites><orcidid>0000-0001-9916-116X</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.23484$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchir.23484$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/35689412$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wang, Hou</creatorcontrib><creatorcontrib>Yang, Yanning</creatorcontrib><creatorcontrib>Chen, Shuhuan</creatorcontrib><creatorcontrib>Xiao, Wenjie</creatorcontrib><creatorcontrib>Hu, Kangyu</creatorcontrib><creatorcontrib>Zhong, Changyuan</creatorcontrib><creatorcontrib>Ouyang, Junying</creatorcontrib><creatorcontrib>Liu, Xiong</creatorcontrib><title>Enantioseparation of amino acid and mandelic acid enantiomers using Garphos derivatives as chiral extractants</title><title>Chirality (New York, N.Y.)</title><addtitle>Chirality</addtitle><description>In this paper, Garphos with different substituents were employed as chiral extractants to enantioseparate racemic amino acid and mandelic acid. The influences of metal precursors, pH of aqueous solution, Garphos‐metal concentration, extraction temperature, and substituent effect on extraction were investigated. The results indicated that the substituent groups significantly affected the π‐π interaction between extractant and substrate. And the separation factors (α) for Garphos could be remarkably improved by regulating substituent groups. Garphos‐II‐Pd, Garphos‐VI‐Pd, Garphos‐III‐Pd, Garphos‐I‐Cu, Garphos‐VI‐Cu, and Garphos‐V‐Pd were the most efficient extractants for phenylalanine (Phe), homophenylalanine (Hphe), 4‐nitrophenylalanine (Nphe), 3‐chlorophenylglycine (Cpheg), mandelic acid (MA), and 2‐chlormandelic acid (CMA) with α values of 2.40, 2.37, 5.37, 1.59, 5.98, and 3.69, respectively. This work provided an important reference for the design of efficient chiral extractants in future work.</description><subject>amino acid</subject><subject>Amino acids</subject><subject>Aqueous solutions</subject><subject>Copper</subject><subject>Enantiomers</subject><subject>enantioseparation</subject><subject>Extractants</subject><subject>Garphos</subject><subject>mandelic acid</subject><subject>Metal concentrations</subject><subject>Palladium</subject><subject>Phenylalanine</subject><subject>substituent effect</subject><subject>Substrates</subject><issn>0899-0042</issn><issn>1520-636X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNp9kUtLXTEQgENpqVfbjT-gBLopwrF5n2QpF6uCUCgV3IUxmaOR87gm9_j4983tsV100c3MEL75mMwQcsjZMWdMfA13KR8Lqax6Q1ZcC9YYaa7fkhWzzjWMKbFH9ku5Z4w5I9V7sie1sU5xsSLD6QjjNk0FN5ChFiOdOgpDGicKIUUKY6RDDdinsLzg0jFgLnQuabylZ5A3d1OhEXN6rJJHLBQK3c0FPcXnbYawrU3lA3nXQV_w42s-IFffTn-uz5vL72cX65PLJgjbqsaZwFpp0XLTxaC1RHZjlOIRlJWxiw60VEEHG3QULQjrogsIoLiqhbPygHxZvJs8PcxYtn5IJWDfw4jTXLwwrTaMy3aHfv4HvZ_mPNbpvGjr7nQFZaWOFirkqZSMnd_kNEB-8Zz53RH87rP-9xEq_OlVOd8MGP-if7ZeAb4AT6nHl_-o_Pr84sci_QUcS5ME</recordid><startdate>202209</startdate><enddate>202209</enddate><creator>Wang, Hou</creator><creator>Yang, Yanning</creator><creator>Chen, Shuhuan</creator><creator>Xiao, Wenjie</creator><creator>Hu, Kangyu</creator><creator>Zhong, Changyuan</creator><creator>Ouyang, Junying</creator><creator>Liu, Xiong</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</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>7X8</scope><orcidid>https://orcid.org/0000-0001-9916-116X</orcidid></search><sort><creationdate>202209</creationdate><title>Enantioseparation of amino acid and mandelic acid enantiomers using Garphos derivatives as chiral extractants</title><author>Wang, Hou ; Yang, Yanning ; Chen, Shuhuan ; Xiao, Wenjie ; Hu, Kangyu ; Zhong, Changyuan ; Ouyang, Junying ; Liu, Xiong</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2874-96c0738e816fdc553e0b6441da483dfd9a534c5c8c5d27a289d9ceaa414d9c983</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>amino acid</topic><topic>Amino acids</topic><topic>Aqueous solutions</topic><topic>Copper</topic><topic>Enantiomers</topic><topic>enantioseparation</topic><topic>Extractants</topic><topic>Garphos</topic><topic>mandelic acid</topic><topic>Metal concentrations</topic><topic>Palladium</topic><topic>Phenylalanine</topic><topic>substituent effect</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wang, Hou</creatorcontrib><creatorcontrib>Yang, Yanning</creatorcontrib><creatorcontrib>Chen, Shuhuan</creatorcontrib><creatorcontrib>Xiao, Wenjie</creatorcontrib><creatorcontrib>Hu, Kangyu</creatorcontrib><creatorcontrib>Zhong, Changyuan</creatorcontrib><creatorcontrib>Ouyang, Junying</creatorcontrib><creatorcontrib>Liu, Xiong</creatorcontrib><collection>PubMed</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>MEDLINE - Academic</collection><jtitle>Chirality (New York, N.Y.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wang, Hou</au><au>Yang, Yanning</au><au>Chen, Shuhuan</au><au>Xiao, Wenjie</au><au>Hu, Kangyu</au><au>Zhong, Changyuan</au><au>Ouyang, Junying</au><au>Liu, Xiong</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enantioseparation of amino acid and mandelic acid enantiomers using Garphos derivatives as chiral extractants</atitle><jtitle>Chirality (New York, N.Y.)</jtitle><addtitle>Chirality</addtitle><date>2022-09</date><risdate>2022</risdate><volume>34</volume><issue>9</issue><spage>1239</spage><epage>1246</epage><pages>1239-1246</pages><issn>0899-0042</issn><eissn>1520-636X</eissn><abstract>In this paper, Garphos with different substituents were employed as chiral extractants to enantioseparate racemic amino acid and mandelic acid. The influences of metal precursors, pH of aqueous solution, Garphos‐metal concentration, extraction temperature, and substituent effect on extraction were investigated. The results indicated that the substituent groups significantly affected the π‐π interaction between extractant and substrate. And the separation factors (α) for Garphos could be remarkably improved by regulating substituent groups. Garphos‐II‐Pd, Garphos‐VI‐Pd, Garphos‐III‐Pd, Garphos‐I‐Cu, Garphos‐VI‐Cu, and Garphos‐V‐Pd were the most efficient extractants for phenylalanine (Phe), homophenylalanine (Hphe), 4‐nitrophenylalanine (Nphe), 3‐chlorophenylglycine (Cpheg), mandelic acid (MA), and 2‐chlormandelic acid (CMA) with α values of 2.40, 2.37, 5.37, 1.59, 5.98, and 3.69, respectively. This work provided an important reference for the design of efficient chiral extractants in future work.</abstract><cop>United States</cop><pub>Wiley Subscription Services, Inc</pub><pmid>35689412</pmid><doi>10.1002/chir.23484</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0001-9916-116X</orcidid></addata></record> |
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| subjects | amino acid Amino acids Aqueous solutions Copper Enantiomers enantioseparation Extractants Garphos mandelic acid Metal concentrations Palladium Phenylalanine substituent effect Substrates |
| title | Enantioseparation of amino acid and mandelic acid enantiomers using Garphos derivatives as chiral extractants |
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