Exploration of the Four-Dimensional-Conformational Potential Energy Hypersurface of N-Acetyl-l-aspartic Acid N‘-Methylamide with Its Internally Hydrogen Bonded Side-Chain Orientation

Exploration of the Four-Dimensional-Conformational Potential Energy Hypersurface of N-Acetyl-l-aspartic Acid N‘-Methylamide with Its Internally Hydrogen Bonded Side-Chain Orientation

Side-chain conformational potential energy hypersurfaces have been generated and analyzed for each of the nine possible backbone conformers of N-acetyl-l-aspartic acid-N‘ methylamide. A total of 37 out of the 81 possible conformers were found and optimized at the B3LYP/6-31G(d) level of theory. The...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment, & general theory Molecules, spectroscopy, kinetics, environment, & general theory, 2002-08, Vol.106 (30), p.6999-7009
Hauptverfasser: Koo, Joseph C. P, Chass, Gregory A, Perczel, Andras, Farkas, Ödon, Torday, Ladislaus L, Varro, Andras, Papp, Julius Gy, Csizmadia, Imre G
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 7009
container_issue 30
container_start_page 6999
container_title The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment, & general theory
container_volume 106
creator Koo, Joseph C. P
Chass, Gregory A
Perczel, Andras
Farkas, Ödon
Torday, Ladislaus L
Varro, Andras
Papp, Julius Gy
Csizmadia, Imre G
description Side-chain conformational potential energy hypersurfaces have been generated and analyzed for each of the nine possible backbone conformers of N-acetyl-l-aspartic acid-N‘ methylamide. A total of 37 out of the 81 possible conformers were found and optimized at the B3LYP/6-31G(d) level of theory. The relative energies as well as the stabilization exerted by the side-chain on the backbone have been calculated, at this level of theory, for the 37 optimized conformers. Various backbone-backbone (N−H···OC) and backbone-side-chain (N−H···OC; N−H···OH) hydrogen bonds were analyzed. The appearance of the notoriously absent αL backbone conformer was attributed to such a backbone-side-chain (BB−SC) hydrogen bonds as well as a very unusual backbone-backbone (BB−BB) hydrogen bond.
doi_str_mv 10.1021/jp014514b
format Article
fullrecord <record><control><sourceid>acs_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1021_jp014514b</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>a199866034</sourcerecordid><originalsourceid>FETCH-LOGICAL-a330t-b835a00516befaf8f5101d5956060b68ad9e8ba35bdfa3d3de2b287adee4514b3</originalsourceid><addsrcrecordid>eNptkDtuGzEQQBdBAsSxXeQGbFKkYEwuxdWqVGQpFuCPANtNGmJ2ObSorMgFScPeLsfIUXyenCSUZLhKxQHx8GbwiuIzZ984K_nZpmd8JPmoeVcccVkyKksu3-eZ1RMqKzH5WHyKccMY46IcHRUv8-e-8wGS9Y54Q9IaycI_Bnput-hi_oWOzrwzPmz3EHRk5RO6ZPM0dxgeBnIx9BjiYzDQ4k5yTactpqGjHYXYQ0i2JdPWanL99_cfeoVpPXSwtRrJk01rskyRLF3CkOXdzqaDf0BHvnunUZPbDNLZGqwjN8Hmzfs7TooPBrqIp6_vcXG_mN_NLujlzY_lbHpJQQiWaFMLCYxJXjVowNRGcsa1nMiKVaypatATrBsQstEGhBYay6asx6AR9xnFcfH14G2DjzGgUX2wWwiD4kztkqu35JmlB9bGhM9vIIRfqhqLsVR3q1sl6sX51U9Zq1Xmvxx4aKPa5Oo5QPyP9x_WKJSJ</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Exploration of the Four-Dimensional-Conformational Potential Energy Hypersurface of N-Acetyl-l-aspartic Acid N‘-Methylamide with Its Internally Hydrogen Bonded Side-Chain Orientation</title><source>American Chemical Society Journals</source><creator>Koo, Joseph C. P ; Chass, Gregory A ; Perczel, Andras ; Farkas, Ödon ; Torday, Ladislaus L ; Varro, Andras ; Papp, Julius Gy ; Csizmadia, Imre G</creator><creatorcontrib>Koo, Joseph C. P ; Chass, Gregory A ; Perczel, Andras ; Farkas, Ödon ; Torday, Ladislaus L ; Varro, Andras ; Papp, Julius Gy ; Csizmadia, Imre G</creatorcontrib><description>Side-chain conformational potential energy hypersurfaces have been generated and analyzed for each of the nine possible backbone conformers of N-acetyl-l-aspartic acid-N‘ methylamide. A total of 37 out of the 81 possible conformers were found and optimized at the B3LYP/6-31G(d) level of theory. The relative energies as well as the stabilization exerted by the side-chain on the backbone have been calculated, at this level of theory, for the 37 optimized conformers. Various backbone-backbone (N−H···OC) and backbone-side-chain (N−H···OC; N−H···OH) hydrogen bonds were analyzed. The appearance of the notoriously absent αL backbone conformer was attributed to such a backbone-side-chain (BB−SC) hydrogen bonds as well as a very unusual backbone-backbone (BB−BB) hydrogen bond.</description><identifier>ISSN: 1089-5639</identifier><identifier>EISSN: 1520-5215</identifier><identifier>DOI: 10.1021/jp014514b</identifier><language>eng</language><publisher>American Chemical Society</publisher><ispartof>The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment, &amp; general theory, 2002-08, Vol.106 (30), p.6999-7009</ispartof><rights>Copyright © 2002 American Chemical Society</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a330t-b835a00516befaf8f5101d5956060b68ad9e8ba35bdfa3d3de2b287adee4514b3</citedby><cites>FETCH-LOGICAL-a330t-b835a00516befaf8f5101d5956060b68ad9e8ba35bdfa3d3de2b287adee4514b3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jp014514b$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jp014514b$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids></links><search><creatorcontrib>Koo, Joseph C. P</creatorcontrib><creatorcontrib>Chass, Gregory A</creatorcontrib><creatorcontrib>Perczel, Andras</creatorcontrib><creatorcontrib>Farkas, Ödon</creatorcontrib><creatorcontrib>Torday, Ladislaus L</creatorcontrib><creatorcontrib>Varro, Andras</creatorcontrib><creatorcontrib>Papp, Julius Gy</creatorcontrib><creatorcontrib>Csizmadia, Imre G</creatorcontrib><title>Exploration of the Four-Dimensional-Conformational Potential Energy Hypersurface of N-Acetyl-l-aspartic Acid N‘-Methylamide with Its Internally Hydrogen Bonded Side-Chain Orientation</title><title>The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment, &amp; general theory</title><addtitle>J. Phys. Chem. A</addtitle><description>Side-chain conformational potential energy hypersurfaces have been generated and analyzed for each of the nine possible backbone conformers of N-acetyl-l-aspartic acid-N‘ methylamide. A total of 37 out of the 81 possible conformers were found and optimized at the B3LYP/6-31G(d) level of theory. The relative energies as well as the stabilization exerted by the side-chain on the backbone have been calculated, at this level of theory, for the 37 optimized conformers. Various backbone-backbone (N−H···OC) and backbone-side-chain (N−H···OC; N−H···OH) hydrogen bonds were analyzed. The appearance of the notoriously absent αL backbone conformer was attributed to such a backbone-side-chain (BB−SC) hydrogen bonds as well as a very unusual backbone-backbone (BB−BB) hydrogen bond.</description><issn>1089-5639</issn><issn>1520-5215</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2002</creationdate><recordtype>article</recordtype><recordid>eNptkDtuGzEQQBdBAsSxXeQGbFKkYEwuxdWqVGQpFuCPANtNGmJ2ObSorMgFScPeLsfIUXyenCSUZLhKxQHx8GbwiuIzZ984K_nZpmd8JPmoeVcccVkyKksu3-eZ1RMqKzH5WHyKccMY46IcHRUv8-e-8wGS9Y54Q9IaycI_Bnput-hi_oWOzrwzPmz3EHRk5RO6ZPM0dxgeBnIx9BjiYzDQ4k5yTactpqGjHYXYQ0i2JdPWanL99_cfeoVpPXSwtRrJk01rskyRLF3CkOXdzqaDf0BHvnunUZPbDNLZGqwjN8Hmzfs7TooPBrqIp6_vcXG_mN_NLujlzY_lbHpJQQiWaFMLCYxJXjVowNRGcsa1nMiKVaypatATrBsQstEGhBYay6asx6AR9xnFcfH14G2DjzGgUX2wWwiD4kztkqu35JmlB9bGhM9vIIRfqhqLsVR3q1sl6sX51U9Zq1Xmvxx4aKPa5Oo5QPyP9x_WKJSJ</recordid><startdate>20020801</startdate><enddate>20020801</enddate><creator>Koo, Joseph C. P</creator><creator>Chass, Gregory A</creator><creator>Perczel, Andras</creator><creator>Farkas, Ödon</creator><creator>Torday, Ladislaus L</creator><creator>Varro, Andras</creator><creator>Papp, Julius Gy</creator><creator>Csizmadia, Imre G</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20020801</creationdate><title>Exploration of the Four-Dimensional-Conformational Potential Energy Hypersurface of N-Acetyl-l-aspartic Acid N‘-Methylamide with Its Internally Hydrogen Bonded Side-Chain Orientation</title><author>Koo, Joseph C. P ; Chass, Gregory A ; Perczel, Andras ; Farkas, Ödon ; Torday, Ladislaus L ; Varro, Andras ; Papp, Julius Gy ; Csizmadia, Imre G</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a330t-b835a00516befaf8f5101d5956060b68ad9e8ba35bdfa3d3de2b287adee4514b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2002</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Koo, Joseph C. P</creatorcontrib><creatorcontrib>Chass, Gregory A</creatorcontrib><creatorcontrib>Perczel, Andras</creatorcontrib><creatorcontrib>Farkas, Ödon</creatorcontrib><creatorcontrib>Torday, Ladislaus L</creatorcontrib><creatorcontrib>Varro, Andras</creatorcontrib><creatorcontrib>Papp, Julius Gy</creatorcontrib><creatorcontrib>Csizmadia, Imre G</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><jtitle>The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment, &amp; general theory</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Koo, Joseph C. P</au><au>Chass, Gregory A</au><au>Perczel, Andras</au><au>Farkas, Ödon</au><au>Torday, Ladislaus L</au><au>Varro, Andras</au><au>Papp, Julius Gy</au><au>Csizmadia, Imre G</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Exploration of the Four-Dimensional-Conformational Potential Energy Hypersurface of N-Acetyl-l-aspartic Acid N‘-Methylamide with Its Internally Hydrogen Bonded Side-Chain Orientation</atitle><jtitle>The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment, &amp; general theory</jtitle><addtitle>J. Phys. Chem. A</addtitle><date>2002-08-01</date><risdate>2002</risdate><volume>106</volume><issue>30</issue><spage>6999</spage><epage>7009</epage><pages>6999-7009</pages><issn>1089-5639</issn><eissn>1520-5215</eissn><abstract>Side-chain conformational potential energy hypersurfaces have been generated and analyzed for each of the nine possible backbone conformers of N-acetyl-l-aspartic acid-N‘ methylamide. A total of 37 out of the 81 possible conformers were found and optimized at the B3LYP/6-31G(d) level of theory. The relative energies as well as the stabilization exerted by the side-chain on the backbone have been calculated, at this level of theory, for the 37 optimized conformers. Various backbone-backbone (N−H···OC) and backbone-side-chain (N−H···OC; N−H···OH) hydrogen bonds were analyzed. The appearance of the notoriously absent αL backbone conformer was attributed to such a backbone-side-chain (BB−SC) hydrogen bonds as well as a very unusual backbone-backbone (BB−BB) hydrogen bond.</abstract><pub>American Chemical Society</pub><doi>10.1021/jp014514b</doi><tpages>11</tpages><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 1089-5639
ispartof The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment, & general theory, 2002-08, Vol.106 (30), p.6999-7009
issn 1089-5639
1520-5215
language eng
recordid cdi_crossref_primary_10_1021_jp014514b
source American Chemical Society Journals
title Exploration of the Four-Dimensional-Conformational Potential Energy Hypersurface of N-Acetyl-l-aspartic Acid N‘-Methylamide with Its Internally Hydrogen Bonded Side-Chain Orientation
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-27T14%3A14%3A40IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-acs_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Exploration%20of%20the%20Four-Dimensional-Conformational%20Potential%20Energy%20Hypersurface%20of%20N-Acetyl-l-aspartic%20Acid%20N%E2%80%98-Methylamide%20with%20Its%20Internally%20Hydrogen%20Bonded%20Side-Chain%20Orientation&rft.jtitle=The%20journal%20of%20physical%20chemistry.%20A,%20Molecules,%20spectroscopy,%20kinetics,%20environment,%20&%20general%20theory&rft.au=Koo,%20Joseph%20C.%20P&rft.date=2002-08-01&rft.volume=106&rft.issue=30&rft.spage=6999&rft.epage=7009&rft.pages=6999-7009&rft.issn=1089-5639&rft.eissn=1520-5215&rft_id=info:doi/10.1021/jp014514b&rft_dat=%3Cacs_cross%3Ea199866034%3C/acs_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true