Peptide nanotube aligning side chains onto one side
A novel pseudo cyclic penta‐β‐peptide composed of a β‐naphthylalanine, two β‐alanines, and a sequence of ethylenediamine‐succinic acid (CP5ES) is synthesized and investigated on peptide nanotube (PNT) formation. When the PNT is formed with the maximum number of intermolecular hydrogen bonds between...
Gespeichert in:
| Veröffentlicht in: | Journal of peptide science 2016-06, Vol.22 (6), p.391-396 |
|---|---|
| Hauptverfasser: | , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 396 |
|---|---|
| container_issue | 6 |
| container_start_page | 391 |
| container_title | Journal of peptide science |
| container_volume | 22 |
| creator | Tabata, Yuki Mitani, Shota Kimura, Shunsaku |
| description | A novel pseudo cyclic penta‐β‐peptide composed of a β‐naphthylalanine, two β‐alanines, and a sequence of ethylenediamine‐succinic acid (CP5ES) is synthesized and investigated on peptide nanotube (PNT) formation. When the PNT is formed with the maximum number of intermolecular hydrogen bonds between the cyclic peptides, the sequence enables the alignment of the side chains, naphthyl groups, on one side of the PNT. Microscopic and spectroscopic observations of CP5ES crystals reveal that CP5ES forms rod‐ or needle‐shaped molecular assemblies showing exciton coupling of the Cotton effect and predominant monomer emission, which are different from a reference cyclic tri‐β‐peptide composed of a β‐naphthylalanine and two β‐alanines. Insertion of a sequence of ethylenediamine‐succinic acid into β‐amino acids in the cyclic skeleton is therefore suggested to be effective to make the side chains aligning on one side of the PNT. Copyright © 2016 European Peptide Society and John Wiley & Sons, Ltd.
A novel pseudo cyclic β‐peptide with a sequence of ethylenediamine‐succinic acid is synthesized and investigated on PNT formation. With the sequence, the maximum number of intermolecular hydrogen bonds between the cyclic peptides are available only when the side chains, naphthyl groups, align at the same side. |
| doi_str_mv | 10.1002/psc.2881 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1808688096</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>4087156711</sourcerecordid><originalsourceid>FETCH-LOGICAL-c4861-aab8473842e4e30c2ad50cf3a19b12b2b11a463785a305a6ef0aea0b6650d1bf3</originalsourceid><addsrcrecordid>eNqF0F1LwzAUBuAgitMp-Atk4I03nTlJ89FLGboJQwubKN6EtE1nZ9fWpkX37223OkEQb5Jw8vDCeRE6AzwEjMlVYcMhkRL20BFgz3OASrHfvgVzCAfRQ8fWLjFu_hg_RD0iiCRA2RGivimqJDKDTGd5VQdmoNNkkSXZYmDbcfiqk8wO8qzKm8NshifoINapNafd3UePtzfz0cSZPozvRtdTJ3QlB0frQLqCSpcY11AcEh0xHMZUgxcACUgAoF1OhWSaYqa5ibE2GgecMxxBENM-utzmFmX-XhtbqVViQ5OmOjN5bRVILLmU2OP_U-GxxhLa0otfdJnXZdYsslEeBwnyJzAsc2tLE6uiTFa6XCvAqu1cNZ2rtvOGnneBdbAy0Q5-l9wAZws-ktSs_wxS_mzUBXY-sZX53HldvikuqGDq6X6sfJiIl9ncV8_0C4Mzl0E</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1795961818</pqid></control><display><type>article</type><title>Peptide nanotube aligning side chains onto one side</title><source>MEDLINE</source><source>Wiley Online Library All Journals</source><creator>Tabata, Yuki ; Mitani, Shota ; Kimura, Shunsaku</creator><creatorcontrib>Tabata, Yuki ; Mitani, Shota ; Kimura, Shunsaku</creatorcontrib><description>A novel pseudo cyclic penta‐β‐peptide composed of a β‐naphthylalanine, two β‐alanines, and a sequence of ethylenediamine‐succinic acid (CP5ES) is synthesized and investigated on peptide nanotube (PNT) formation. When the PNT is formed with the maximum number of intermolecular hydrogen bonds between the cyclic peptides, the sequence enables the alignment of the side chains, naphthyl groups, on one side of the PNT. Microscopic and spectroscopic observations of CP5ES crystals reveal that CP5ES forms rod‐ or needle‐shaped molecular assemblies showing exciton coupling of the Cotton effect and predominant monomer emission, which are different from a reference cyclic tri‐β‐peptide composed of a β‐naphthylalanine and two β‐alanines. Insertion of a sequence of ethylenediamine‐succinic acid into β‐amino acids in the cyclic skeleton is therefore suggested to be effective to make the side chains aligning on one side of the PNT. Copyright © 2016 European Peptide Society and John Wiley & Sons, Ltd.
A novel pseudo cyclic β‐peptide with a sequence of ethylenediamine‐succinic acid is synthesized and investigated on PNT formation. With the sequence, the maximum number of intermolecular hydrogen bonds between the cyclic peptides are available only when the side chains, naphthyl groups, align at the same side.</description><identifier>ISSN: 1075-2617</identifier><identifier>EISSN: 1099-1387</identifier><identifier>DOI: 10.1002/psc.2881</identifier><identifier>PMID: 27282135</identifier><identifier>CODEN: JPSIEI</identifier><language>eng</language><publisher>England: Blackwell Publishing Ltd</publisher><subject>beta-Alanine - analogs & derivatives ; beta-Alanine - chemistry ; cyclic peptide ; Ethylenediamines - chemistry ; Hydrogen Bonding ; Molecular Structure ; Nanotubes, Peptide - chemistry ; peptide nanotube ; Peptides ; Peptides, Cyclic - chemical synthesis ; Peptides, Cyclic - chemistry ; self-assembly ; Succinates - chemistry ; β-amino acid</subject><ispartof>Journal of peptide science, 2016-06, Vol.22 (6), p.391-396</ispartof><rights>Copyright © 2016 European Peptide Society and John Wiley & Sons, Ltd.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4861-aab8473842e4e30c2ad50cf3a19b12b2b11a463785a305a6ef0aea0b6650d1bf3</citedby><cites>FETCH-LOGICAL-c4861-aab8473842e4e30c2ad50cf3a19b12b2b11a463785a305a6ef0aea0b6650d1bf3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fpsc.2881$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fpsc.2881$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1416,27922,27923,45572,45573</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/27282135$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Tabata, Yuki</creatorcontrib><creatorcontrib>Mitani, Shota</creatorcontrib><creatorcontrib>Kimura, Shunsaku</creatorcontrib><title>Peptide nanotube aligning side chains onto one side</title><title>Journal of peptide science</title><addtitle>J. Pept. Sci</addtitle><description>A novel pseudo cyclic penta‐β‐peptide composed of a β‐naphthylalanine, two β‐alanines, and a sequence of ethylenediamine‐succinic acid (CP5ES) is synthesized and investigated on peptide nanotube (PNT) formation. When the PNT is formed with the maximum number of intermolecular hydrogen bonds between the cyclic peptides, the sequence enables the alignment of the side chains, naphthyl groups, on one side of the PNT. Microscopic and spectroscopic observations of CP5ES crystals reveal that CP5ES forms rod‐ or needle‐shaped molecular assemblies showing exciton coupling of the Cotton effect and predominant monomer emission, which are different from a reference cyclic tri‐β‐peptide composed of a β‐naphthylalanine and two β‐alanines. Insertion of a sequence of ethylenediamine‐succinic acid into β‐amino acids in the cyclic skeleton is therefore suggested to be effective to make the side chains aligning on one side of the PNT. Copyright © 2016 European Peptide Society and John Wiley & Sons, Ltd.
A novel pseudo cyclic β‐peptide with a sequence of ethylenediamine‐succinic acid is synthesized and investigated on PNT formation. With the sequence, the maximum number of intermolecular hydrogen bonds between the cyclic peptides are available only when the side chains, naphthyl groups, align at the same side.</description><subject>beta-Alanine - analogs & derivatives</subject><subject>beta-Alanine - chemistry</subject><subject>cyclic peptide</subject><subject>Ethylenediamines - chemistry</subject><subject>Hydrogen Bonding</subject><subject>Molecular Structure</subject><subject>Nanotubes, Peptide - chemistry</subject><subject>peptide nanotube</subject><subject>Peptides</subject><subject>Peptides, Cyclic - chemical synthesis</subject><subject>Peptides, Cyclic - chemistry</subject><subject>self-assembly</subject><subject>Succinates - chemistry</subject><subject>β-amino acid</subject><issn>1075-2617</issn><issn>1099-1387</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqF0F1LwzAUBuAgitMp-Atk4I03nTlJ89FLGboJQwubKN6EtE1nZ9fWpkX37223OkEQb5Jw8vDCeRE6AzwEjMlVYcMhkRL20BFgz3OASrHfvgVzCAfRQ8fWLjFu_hg_RD0iiCRA2RGivimqJDKDTGd5VQdmoNNkkSXZYmDbcfiqk8wO8qzKm8NshifoINapNafd3UePtzfz0cSZPozvRtdTJ3QlB0frQLqCSpcY11AcEh0xHMZUgxcACUgAoF1OhWSaYqa5ibE2GgecMxxBENM-utzmFmX-XhtbqVViQ5OmOjN5bRVILLmU2OP_U-GxxhLa0otfdJnXZdYsslEeBwnyJzAsc2tLE6uiTFa6XCvAqu1cNZ2rtvOGnneBdbAy0Q5-l9wAZws-ktSs_wxS_mzUBXY-sZX53HldvikuqGDq6X6sfJiIl9ncV8_0C4Mzl0E</recordid><startdate>201606</startdate><enddate>201606</enddate><creator>Tabata, Yuki</creator><creator>Mitani, Shota</creator><creator>Kimura, Shunsaku</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><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>7QO</scope><scope>7TK</scope><scope>8FD</scope><scope>FR3</scope><scope>K9.</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>201606</creationdate><title>Peptide nanotube aligning side chains onto one side</title><author>Tabata, Yuki ; Mitani, Shota ; Kimura, Shunsaku</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4861-aab8473842e4e30c2ad50cf3a19b12b2b11a463785a305a6ef0aea0b6650d1bf3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>beta-Alanine - analogs & derivatives</topic><topic>beta-Alanine - chemistry</topic><topic>cyclic peptide</topic><topic>Ethylenediamines - chemistry</topic><topic>Hydrogen Bonding</topic><topic>Molecular Structure</topic><topic>Nanotubes, Peptide - chemistry</topic><topic>peptide nanotube</topic><topic>Peptides</topic><topic>Peptides, Cyclic - chemical synthesis</topic><topic>Peptides, Cyclic - chemistry</topic><topic>self-assembly</topic><topic>Succinates - chemistry</topic><topic>β-amino acid</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tabata, Yuki</creatorcontrib><creatorcontrib>Mitani, Shota</creatorcontrib><creatorcontrib>Kimura, Shunsaku</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Neurosciences Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of peptide science</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tabata, Yuki</au><au>Mitani, Shota</au><au>Kimura, Shunsaku</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Peptide nanotube aligning side chains onto one side</atitle><jtitle>Journal of peptide science</jtitle><addtitle>J. Pept. Sci</addtitle><date>2016-06</date><risdate>2016</risdate><volume>22</volume><issue>6</issue><spage>391</spage><epage>396</epage><pages>391-396</pages><issn>1075-2617</issn><eissn>1099-1387</eissn><coden>JPSIEI</coden><abstract>A novel pseudo cyclic penta‐β‐peptide composed of a β‐naphthylalanine, two β‐alanines, and a sequence of ethylenediamine‐succinic acid (CP5ES) is synthesized and investigated on peptide nanotube (PNT) formation. When the PNT is formed with the maximum number of intermolecular hydrogen bonds between the cyclic peptides, the sequence enables the alignment of the side chains, naphthyl groups, on one side of the PNT. Microscopic and spectroscopic observations of CP5ES crystals reveal that CP5ES forms rod‐ or needle‐shaped molecular assemblies showing exciton coupling of the Cotton effect and predominant monomer emission, which are different from a reference cyclic tri‐β‐peptide composed of a β‐naphthylalanine and two β‐alanines. Insertion of a sequence of ethylenediamine‐succinic acid into β‐amino acids in the cyclic skeleton is therefore suggested to be effective to make the side chains aligning on one side of the PNT. Copyright © 2016 European Peptide Society and John Wiley & Sons, Ltd.
A novel pseudo cyclic β‐peptide with a sequence of ethylenediamine‐succinic acid is synthesized and investigated on PNT formation. With the sequence, the maximum number of intermolecular hydrogen bonds between the cyclic peptides are available only when the side chains, naphthyl groups, align at the same side.</abstract><cop>England</cop><pub>Blackwell Publishing Ltd</pub><pmid>27282135</pmid><doi>10.1002/psc.2881</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1075-2617 |
| ispartof | Journal of peptide science, 2016-06, Vol.22 (6), p.391-396 |
| issn | 1075-2617 1099-1387 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1808688096 |
| source | MEDLINE; Wiley Online Library All Journals |
| subjects | beta-Alanine - analogs & derivatives beta-Alanine - chemistry cyclic peptide Ethylenediamines - chemistry Hydrogen Bonding Molecular Structure Nanotubes, Peptide - chemistry peptide nanotube Peptides Peptides, Cyclic - chemical synthesis Peptides, Cyclic - chemistry self-assembly Succinates - chemistry β-amino acid |
| title | Peptide nanotube aligning side chains onto one side |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-09T10%3A52%3A45IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Peptide%20nanotube%20aligning%20side%20chains%20onto%20one%20side&rft.jtitle=Journal%20of%20peptide%20science&rft.au=Tabata,%20Yuki&rft.date=2016-06&rft.volume=22&rft.issue=6&rft.spage=391&rft.epage=396&rft.pages=391-396&rft.issn=1075-2617&rft.eissn=1099-1387&rft.coden=JPSIEI&rft_id=info:doi/10.1002/psc.2881&rft_dat=%3Cproquest_cross%3E4087156711%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1795961818&rft_id=info:pmid/27282135&rfr_iscdi=true |