Infrared multiple photon dissociation action spectroscopy of protonated glycine, histidine, lysine, and arginine complexed with 18-crown-6 ether
Complexes of 18-crown-6 ether (18C6) with four protonated amino acids (AAs) are examined using infrared multiple photon dissociation (IRMPD) action spectroscopy utilizing light generated by the infrared free electron laser at the Centre Laser Infrarouge d'Orsay (CLIO). The AAs examined in this...
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| creator | McNary, Christopher P Nei, Y.-W Maitre, Philippe Rodgers, M. T Armentrout, P. B |
| description | Complexes of 18-crown-6 ether (18C6) with four protonated amino acids (AAs) are examined using infrared multiple photon dissociation (IRMPD) action spectroscopy utilizing light generated by the infrared free electron laser at the Centre Laser Infrarouge d'Orsay (CLIO). The AAs examined in this work include glycine (Gly) and the three basic AAs: histidine (His), lysine (Lys), and arginine (Arg). To identify the (AA)H
+
(18C6) conformations present in the experimental studies, the measured IRMPD spectra are compared to spectra calculated at the B3LYP/6-311+G(d,p) level of theory. Relative energies of various conformers and isomers are provided by single point energy calculations carried out at the B3LYP, B3P86, M06, and MP2(full) levels using the 6-311+G(2p,2d) basis set. The comparisons between the IRMPD and theoretical IR spectra indicate that 18C6 binds to Gly and His
via
the protonated backbone amino group, whereas protonated Lys prefers binding
via
the protonated side-chain amino group. Results for Arg are less definitive with strong evidence for binding to the protonated guanidino side chain (the calculated ground conformer at most levels of theory), but contributions from backbone binding to a zwitterionic structure are likely.
IRMPD action spectroscopy elucidates the binding modes of protonated amino acids with 18C6 crown ether. |
| doi_str_mv | 10.1039/c9cp02265a |
| format | Article |
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+
(18C6) conformations present in the experimental studies, the measured IRMPD spectra are compared to spectra calculated at the B3LYP/6-311+G(d,p) level of theory. Relative energies of various conformers and isomers are provided by single point energy calculations carried out at the B3LYP, B3P86, M06, and MP2(full) levels using the 6-311+G(2p,2d) basis set. The comparisons between the IRMPD and theoretical IR spectra indicate that 18C6 binds to Gly and His
via
the protonated backbone amino group, whereas protonated Lys prefers binding
via
the protonated side-chain amino group. Results for Arg are less definitive with strong evidence for binding to the protonated guanidino side chain (the calculated ground conformer at most levels of theory), but contributions from backbone binding to a zwitterionic structure are likely.
IRMPD action spectroscopy elucidates the binding modes of protonated amino acids with 18C6 crown ether.</description><identifier>ISSN: 1463-9076</identifier><identifier>EISSN: 1463-9084</identifier><identifier>DOI: 10.1039/c9cp02265a</identifier><identifier>PMID: 31155616</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Amino acids ; Analytical chemistry ; Backbone ; Binding ; Chains ; Chemical Sciences ; Free electron lasers ; Glycine ; Histidine ; Infrared lasers ; Infrared spectroscopy ; Isomers ; Levels ; Lysine ; Mathematical analysis ; Molecular conformation ; Spectra ; Spectrum analysis ; Theory</subject><ispartof>Physical chemistry chemical physics : PCCP, 2019-06, Vol.21 (23), p.12625-12639</ispartof><rights>Copyright Royal Society of Chemistry 2019</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c434t-4f17b68a492e9c6019ea91ac77644555374a30b672ce0fc8482d795af4829edf3</citedby><cites>FETCH-LOGICAL-c434t-4f17b68a492e9c6019ea91ac77644555374a30b672ce0fc8482d795af4829edf3</cites><orcidid>0000-0003-2924-1054 ; 0000-0003-2953-6039 ; 0000-0002-5614-0948</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,314,776,780,881,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31155616$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.science/hal-02334561$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>McNary, Christopher P</creatorcontrib><creatorcontrib>Nei, Y.-W</creatorcontrib><creatorcontrib>Maitre, Philippe</creatorcontrib><creatorcontrib>Rodgers, M. T</creatorcontrib><creatorcontrib>Armentrout, P. B</creatorcontrib><title>Infrared multiple photon dissociation action spectroscopy of protonated glycine, histidine, lysine, and arginine complexed with 18-crown-6 ether</title><title>Physical chemistry chemical physics : PCCP</title><addtitle>Phys Chem Chem Phys</addtitle><description>Complexes of 18-crown-6 ether (18C6) with four protonated amino acids (AAs) are examined using infrared multiple photon dissociation (IRMPD) action spectroscopy utilizing light generated by the infrared free electron laser at the Centre Laser Infrarouge d'Orsay (CLIO). The AAs examined in this work include glycine (Gly) and the three basic AAs: histidine (His), lysine (Lys), and arginine (Arg). To identify the (AA)H
+
(18C6) conformations present in the experimental studies, the measured IRMPD spectra are compared to spectra calculated at the B3LYP/6-311+G(d,p) level of theory. Relative energies of various conformers and isomers are provided by single point energy calculations carried out at the B3LYP, B3P86, M06, and MP2(full) levels using the 6-311+G(2p,2d) basis set. The comparisons between the IRMPD and theoretical IR spectra indicate that 18C6 binds to Gly and His
via
the protonated backbone amino group, whereas protonated Lys prefers binding
via
the protonated side-chain amino group. Results for Arg are less definitive with strong evidence for binding to the protonated guanidino side chain (the calculated ground conformer at most levels of theory), but contributions from backbone binding to a zwitterionic structure are likely.
IRMPD action spectroscopy elucidates the binding modes of protonated amino acids with 18C6 crown ether.</description><subject>Amino acids</subject><subject>Analytical chemistry</subject><subject>Backbone</subject><subject>Binding</subject><subject>Chains</subject><subject>Chemical Sciences</subject><subject>Free electron lasers</subject><subject>Glycine</subject><subject>Histidine</subject><subject>Infrared lasers</subject><subject>Infrared spectroscopy</subject><subject>Isomers</subject><subject>Levels</subject><subject>Lysine</subject><subject>Mathematical analysis</subject><subject>Molecular conformation</subject><subject>Spectra</subject><subject>Spectrum analysis</subject><subject>Theory</subject><issn>1463-9076</issn><issn>1463-9084</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNp9ksFu3CAQhlHUqkm2vfTeiiqXNKobMBjDcbVKmkgrpYf2jFiMYyLbuICb7Fv0kYO9yUbqIaeZgW8Gfn4A-IjRd4yIONdCDyjPWaEOwBGmjGQCcfpmn5fsEByHcIcQwgUm78AhwbgoGGZH4N91X3vlTQW7sY12aA0cGhddDysbgtNWRZsKpecQBqOjd0G7YQtdDQc_oSqm9tt2q21vvsHGhmirOW23YY6qr6Dyt7ZPFdSuS6c8pJZ7GxuIeaa9u-8zBk1sjH8P3taqDebDU1yA35cXv1ZX2frmx_Vquc40JTRmtMblhnFFRW6EZggLowRWuiwZpUVRkJIqgjaszLVBteaU51UpClWnRJiqJgvwdTe3Ua0cvO2U30qnrLxaruW0hnJCaHqkvzixpzs26f0zmhBlZ4M2bat648Yg85zQaS7lCT35D71zo--TkoniXAiePFuAsx2VpIfgTb2_AUZy8lSuxOrn7OkywZ-fRo6bzlR79NnEBHzZAT7o_e7Lp5DDLPfTawx5BALCscc</recordid><startdate>20190612</startdate><enddate>20190612</enddate><creator>McNary, Christopher P</creator><creator>Nei, Y.-W</creator><creator>Maitre, Philippe</creator><creator>Rodgers, M. T</creator><creator>Armentrout, P. B</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope><scope>1XC</scope><orcidid>https://orcid.org/0000-0003-2924-1054</orcidid><orcidid>https://orcid.org/0000-0003-2953-6039</orcidid><orcidid>https://orcid.org/0000-0002-5614-0948</orcidid></search><sort><creationdate>20190612</creationdate><title>Infrared multiple photon dissociation action spectroscopy of protonated glycine, histidine, lysine, and arginine complexed with 18-crown-6 ether</title><author>McNary, Christopher P ; Nei, Y.-W ; Maitre, Philippe ; Rodgers, M. T ; Armentrout, P. 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T</creatorcontrib><creatorcontrib>Armentrout, P. B</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><collection>Hyper Article en Ligne (HAL)</collection><jtitle>Physical chemistry chemical physics : PCCP</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>McNary, Christopher P</au><au>Nei, Y.-W</au><au>Maitre, Philippe</au><au>Rodgers, M. T</au><au>Armentrout, P. B</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Infrared multiple photon dissociation action spectroscopy of protonated glycine, histidine, lysine, and arginine complexed with 18-crown-6 ether</atitle><jtitle>Physical chemistry chemical physics : PCCP</jtitle><addtitle>Phys Chem Chem Phys</addtitle><date>2019-06-12</date><risdate>2019</risdate><volume>21</volume><issue>23</issue><spage>12625</spage><epage>12639</epage><pages>12625-12639</pages><issn>1463-9076</issn><eissn>1463-9084</eissn><abstract>Complexes of 18-crown-6 ether (18C6) with four protonated amino acids (AAs) are examined using infrared multiple photon dissociation (IRMPD) action spectroscopy utilizing light generated by the infrared free electron laser at the Centre Laser Infrarouge d'Orsay (CLIO). The AAs examined in this work include glycine (Gly) and the three basic AAs: histidine (His), lysine (Lys), and arginine (Arg). To identify the (AA)H
+
(18C6) conformations present in the experimental studies, the measured IRMPD spectra are compared to spectra calculated at the B3LYP/6-311+G(d,p) level of theory. Relative energies of various conformers and isomers are provided by single point energy calculations carried out at the B3LYP, B3P86, M06, and MP2(full) levels using the 6-311+G(2p,2d) basis set. The comparisons between the IRMPD and theoretical IR spectra indicate that 18C6 binds to Gly and His
via
the protonated backbone amino group, whereas protonated Lys prefers binding
via
the protonated side-chain amino group. Results for Arg are less definitive with strong evidence for binding to the protonated guanidino side chain (the calculated ground conformer at most levels of theory), but contributions from backbone binding to a zwitterionic structure are likely.
IRMPD action spectroscopy elucidates the binding modes of protonated amino acids with 18C6 crown ether.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>31155616</pmid><doi>10.1039/c9cp02265a</doi><tpages>15</tpages><orcidid>https://orcid.org/0000-0003-2924-1054</orcidid><orcidid>https://orcid.org/0000-0003-2953-6039</orcidid><orcidid>https://orcid.org/0000-0002-5614-0948</orcidid></addata></record> |
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| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Amino acids Analytical chemistry Backbone Binding Chains Chemical Sciences Free electron lasers Glycine Histidine Infrared lasers Infrared spectroscopy Isomers Levels Lysine Mathematical analysis Molecular conformation Spectra Spectrum analysis Theory |
| title | Infrared multiple photon dissociation action spectroscopy of protonated glycine, histidine, lysine, and arginine complexed with 18-crown-6 ether |
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