A molecular receptor selective for zwitterionic alanine
A molecular receptor has been synthesized joining an aza-crown ether with a chiral chromane which mimics the oxyanion hole of the enzymes. With this receptor an apolar host-guest complex with zwitterionic alanine has been achieved through the formation of up to seven H-bonds. This complex allows the...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2017, Vol.15 (2), p.477-485 |
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| container_title | Organic & biomolecular chemistry |
| container_volume | 15 |
| creator | Rubio, Omayra H Taouil, Rachid Muñiz, Francisco M Monleón, Laura M Simón, Luis Sanz, Francisca Morán, Joaquín R |
| description | A molecular receptor has been synthesized joining an aza-crown ether with a chiral chromane which mimics the oxyanion hole of the enzymes. With this receptor an apolar host-guest complex with zwitterionic alanine has been achieved through the formation of up to seven H-bonds. This complex allows the extraction of aqueous alanine to a chloroform phase, while other natural amino acids are poorly extracted or are not extracted at all. Due to the chiral nature of the receptor, enantioselective extraction from the aqueous alanine solution to a chloroform phase takes place. X-Ray analysis combined with anisotropic effects, NOE and CD studies revealed the absolute configuration of both strong and weak complexes. Modelling studies also support the proposed structures. The presence of an oxyanion-hole motif in this structure was corroborated by X-ray diffraction studies. |
| doi_str_mv | 10.1039/c6ob02237e |
| format | Article |
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With this receptor an apolar host-guest complex with zwitterionic alanine has been achieved through the formation of up to seven H-bonds. This complex allows the extraction of aqueous alanine to a chloroform phase, while other natural amino acids are poorly extracted or are not extracted at all. Due to the chiral nature of the receptor, enantioselective extraction from the aqueous alanine solution to a chloroform phase takes place. X-Ray analysis combined with anisotropic effects, NOE and CD studies revealed the absolute configuration of both strong and weak complexes. Modelling studies also support the proposed structures. The presence of an oxyanion-hole motif in this structure was corroborated by X-ray diffraction studies.</description><subject>Alanine - chemistry</subject><subject>Alanine - isolation & purification</subject><subject>Aza Compounds - chemistry</subject><subject>Chromans - chemistry</subject><subject>Crown Ethers - chemistry</subject><subject>Crystallography, X-Ray</subject><subject>Hydrogen Bonding</subject><subject>Models, Molecular</subject><subject>Molecular Conformation</subject><subject>Stereoisomerism</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkE1LAzEQhoMotlYv_gDZowirk2TzdaylfkChFz0vSTqBld1uTXYV_fVube3Z08y8PLwMDyGXFG4pcHPnZeuAMa7wiIxpoVQOgpvjw85gRM5SegOgRsnilIyYMsxQLcdETbOmrdH3tY1ZRI-bro1ZwiHqqg_MwnB9f1Zdh7Fq15XPbG3X1RrPyUmwdcKL_ZyQ14f5y-wpXywfn2fTRe45gy5nTnMuAX3wTDirCqktBuMceBakFYGtggoogHIAJbwRaIJCpwpm_Up4PiHXu95NbN97TF3ZVMljPXyBbZ9KqoUptDGU_gMtlNYK5Ba92aE-tilFDOUmVo2NXyWFcuu0nMnl_a_T-QBf7Xt71-DqgP5J5D9X23F_</recordid><startdate>2017</startdate><enddate>2017</enddate><creator>Rubio, Omayra H</creator><creator>Taouil, Rachid</creator><creator>Muñiz, Francisco M</creator><creator>Monleón, Laura M</creator><creator>Simón, Luis</creator><creator>Sanz, Francisca</creator><creator>Morán, Joaquín R</creator><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>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope><orcidid>https://orcid.org/0000-0002-3781-0803</orcidid></search><sort><creationdate>2017</creationdate><title>A molecular receptor selective for zwitterionic alanine</title><author>Rubio, Omayra H ; Taouil, Rachid ; Muñiz, Francisco M ; Monleón, Laura M ; Simón, Luis ; Sanz, Francisca ; Morán, Joaquín R</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c320t-2b83360ecfc25ba7468aef9bb0c2f6a5f2df7fe50130075c95e9f7eb742acd5c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Alanine - chemistry</topic><topic>Alanine - isolation & purification</topic><topic>Aza Compounds - chemistry</topic><topic>Chromans - chemistry</topic><topic>Crown Ethers - chemistry</topic><topic>Crystallography, X-Ray</topic><topic>Hydrogen Bonding</topic><topic>Models, Molecular</topic><topic>Molecular Conformation</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Rubio, Omayra H</creatorcontrib><creatorcontrib>Taouil, Rachid</creatorcontrib><creatorcontrib>Muñiz, Francisco M</creatorcontrib><creatorcontrib>Monleón, Laura M</creatorcontrib><creatorcontrib>Simón, Luis</creatorcontrib><creatorcontrib>Sanz, Francisca</creatorcontrib><creatorcontrib>Morán, Joaquín R</creatorcontrib><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>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Rubio, Omayra H</au><au>Taouil, Rachid</au><au>Muñiz, Francisco M</au><au>Monleón, Laura M</au><au>Simón, Luis</au><au>Sanz, Francisca</au><au>Morán, Joaquín R</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A molecular receptor selective for zwitterionic alanine</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2017</date><risdate>2017</risdate><volume>15</volume><issue>2</issue><spage>477</spage><epage>485</epage><pages>477-485</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>A molecular receptor has been synthesized joining an aza-crown ether with a chiral chromane which mimics the oxyanion hole of the enzymes. With this receptor an apolar host-guest complex with zwitterionic alanine has been achieved through the formation of up to seven H-bonds. This complex allows the extraction of aqueous alanine to a chloroform phase, while other natural amino acids are poorly extracted or are not extracted at all. Due to the chiral nature of the receptor, enantioselective extraction from the aqueous alanine solution to a chloroform phase takes place. X-Ray analysis combined with anisotropic effects, NOE and CD studies revealed the absolute configuration of both strong and weak complexes. Modelling studies also support the proposed structures. The presence of an oxyanion-hole motif in this structure was corroborated by X-ray diffraction studies.</abstract><cop>England</cop><pmid>27929186</pmid><doi>10.1039/c6ob02237e</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0002-3781-0803</orcidid></addata></record> |
| fulltext | fulltext |
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| ispartof | Organic & biomolecular chemistry, 2017, Vol.15 (2), p.477-485 |
| issn | 1477-0520 1477-0539 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1859489911 |
| source | MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Alanine - chemistry Alanine - isolation & purification Aza Compounds - chemistry Chromans - chemistry Crown Ethers - chemistry Crystallography, X-Ray Hydrogen Bonding Models, Molecular Molecular Conformation Stereoisomerism |
| title | A molecular receptor selective for zwitterionic alanine |
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