Non-Hydrogen-Bonded Secondary Structure in β-Peptides: Evidence from Circular Dichroism of (S)-Pyrrolidine-3- carboxylic Acid Oligomers and (S)-Nipecotic Acid Oligomers
Homooligomers of β-amino acids (S)-3-pyrrolidine-3-carboxylic acid (PCA) and (S)-nipecotic acid (Nip) were studied by circular dichroism (CD) in methanol. In each series, a profound change in the far-UV CD spectrum was observed from monomer to tetramer, but little change was observed from tetramer t...
Gespeichert in:
| Veröffentlicht in: | Organic letters 1999-12, Vol.1 (11), p.1717-1720 |
|---|---|
| Hauptverfasser: | , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 1720 |
|---|---|
| container_issue | 11 |
| container_start_page | 1717 |
| container_title | Organic letters |
| container_volume | 1 |
| creator | Huck, Bayard R Langenhan, Joseph M Gellman, Samuel H |
| description | Homooligomers of β-amino acids (S)-3-pyrrolidine-3-carboxylic acid (PCA) and (S)-nipecotic acid (Nip) were studied by circular dichroism (CD) in methanol. In each series, a profound change in the far-UV CD spectrum was observed from monomer to tetramer, but little change was observed from tetramer to hexamer. A comparable pattern is observed in the CD spectra of short proline oligomers. We conclude that both PCA and Nip oligomers with ≥ four residues adopt a characteristic secondary structure. |
| doi_str_mv | 10.1021/ol9909482 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_69482109</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>69482109</sourcerecordid><originalsourceid>FETCH-LOGICAL-a311t-41949467db71524ce95cd229490c69a37c202decb0e52ea1a2f6baf616d228983</originalsourceid><addsrcrecordid>eNptkU1OHDEQha0oKMCQBRdA3gTBwsF29_SM2cHwFwkB0iTrltuuBqNueyh3I2bHlruw4iAcIieJJ4MQUrKqp9JXT1X1CNkU_LvgUuyFRimu8rH8RNbEUGZsxIfy87su-CpZj_GWc5E66gtZFXycFTzja-T5Inh2NrcYrsGzw-AtWDoFk4TGOZ122JuuR6DO09cXdgWzzlmI-78fn-jxfZLeAK0xtHTi0PSNRnrkzA0GF1saaroz3WVXc8TQOOs8sIxRo7EKD_PGGXpgnKWXjbsOLWCk2tu_Axduljbo_gE2yEqtmwhf3-qA_Do5_jk5Y-eXpz8mB-dMZ0J0LBcqV3kxstUo3ZsbUENjpUxNbgqls5GRXFowFYehBC20rItK14UoEjVW42xAtpe-Mwx3PcSubF000DTaQ-hjWSx-LbhK4O4SNBhiRKjLGbo2Pa4UvFxEU75Hk9itN9O-asF-IJdZJODbEtAmlrehR59u_I_RHx9_lxo</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>69482109</pqid></control><display><type>article</type><title>Non-Hydrogen-Bonded Secondary Structure in β-Peptides: Evidence from Circular Dichroism of (S)-Pyrrolidine-3- carboxylic Acid Oligomers and (S)-Nipecotic Acid Oligomers</title><source>MEDLINE</source><source>American Chemical Society Journals</source><creator>Huck, Bayard R ; Langenhan, Joseph M ; Gellman, Samuel H</creator><creatorcontrib>Huck, Bayard R ; Langenhan, Joseph M ; Gellman, Samuel H</creatorcontrib><description>Homooligomers of β-amino acids (S)-3-pyrrolidine-3-carboxylic acid (PCA) and (S)-nipecotic acid (Nip) were studied by circular dichroism (CD) in methanol. In each series, a profound change in the far-UV CD spectrum was observed from monomer to tetramer, but little change was observed from tetramer to hexamer. A comparable pattern is observed in the CD spectra of short proline oligomers. We conclude that both PCA and Nip oligomers with ≥ four residues adopt a characteristic secondary structure.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol9909482</identifier><identifier>PMID: 10836030</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Chromatography, High Pressure Liquid ; Circular Dichroism ; Nipecotic Acids - chemistry ; Peptides - chemistry ; Proline - analogs & derivatives ; Proline - chemistry ; Protein Structure, Secondary ; Pyrrolidines - chemistry ; Spectrophotometry, Ultraviolet</subject><ispartof>Organic letters, 1999-12, Vol.1 (11), p.1717-1720</ispartof><rights>Copyright © 1999 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a311t-41949467db71524ce95cd229490c69a37c202decb0e52ea1a2f6baf616d228983</citedby><cites>FETCH-LOGICAL-a311t-41949467db71524ce95cd229490c69a37c202decb0e52ea1a2f6baf616d228983</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/ol9909482$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol9909482$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/10836030$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Huck, Bayard R</creatorcontrib><creatorcontrib>Langenhan, Joseph M</creatorcontrib><creatorcontrib>Gellman, Samuel H</creatorcontrib><title>Non-Hydrogen-Bonded Secondary Structure in β-Peptides: Evidence from Circular Dichroism of (S)-Pyrrolidine-3- carboxylic Acid Oligomers and (S)-Nipecotic Acid Oligomers</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>Homooligomers of β-amino acids (S)-3-pyrrolidine-3-carboxylic acid (PCA) and (S)-nipecotic acid (Nip) were studied by circular dichroism (CD) in methanol. In each series, a profound change in the far-UV CD spectrum was observed from monomer to tetramer, but little change was observed from tetramer to hexamer. A comparable pattern is observed in the CD spectra of short proline oligomers. We conclude that both PCA and Nip oligomers with ≥ four residues adopt a characteristic secondary structure.</description><subject>Chromatography, High Pressure Liquid</subject><subject>Circular Dichroism</subject><subject>Nipecotic Acids - chemistry</subject><subject>Peptides - chemistry</subject><subject>Proline - analogs & derivatives</subject><subject>Proline - chemistry</subject><subject>Protein Structure, Secondary</subject><subject>Pyrrolidines - chemistry</subject><subject>Spectrophotometry, Ultraviolet</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1999</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkU1OHDEQha0oKMCQBRdA3gTBwsF29_SM2cHwFwkB0iTrltuuBqNueyh3I2bHlruw4iAcIieJJ4MQUrKqp9JXT1X1CNkU_LvgUuyFRimu8rH8RNbEUGZsxIfy87su-CpZj_GWc5E66gtZFXycFTzja-T5Inh2NrcYrsGzw-AtWDoFk4TGOZ122JuuR6DO09cXdgWzzlmI-78fn-jxfZLeAK0xtHTi0PSNRnrkzA0GF1saaroz3WVXc8TQOOs8sIxRo7EKD_PGGXpgnKWXjbsOLWCk2tu_Axduljbo_gE2yEqtmwhf3-qA_Do5_jk5Y-eXpz8mB-dMZ0J0LBcqV3kxstUo3ZsbUENjpUxNbgqls5GRXFowFYehBC20rItK14UoEjVW42xAtpe-Mwx3PcSubF000DTaQ-hjWSx-LbhK4O4SNBhiRKjLGbo2Pa4UvFxEU75Hk9itN9O-asF-IJdZJODbEtAmlrehR59u_I_RHx9_lxo</recordid><startdate>19991202</startdate><enddate>19991202</enddate><creator>Huck, Bayard R</creator><creator>Langenhan, Joseph M</creator><creator>Gellman, Samuel H</creator><general>American Chemical Society</general><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></search><sort><creationdate>19991202</creationdate><title>Non-Hydrogen-Bonded Secondary Structure in β-Peptides: Evidence from Circular Dichroism of (S)-Pyrrolidine-3- carboxylic Acid Oligomers and (S)-Nipecotic Acid Oligomers</title><author>Huck, Bayard R ; Langenhan, Joseph M ; Gellman, Samuel H</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a311t-41949467db71524ce95cd229490c69a37c202decb0e52ea1a2f6baf616d228983</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1999</creationdate><topic>Chromatography, High Pressure Liquid</topic><topic>Circular Dichroism</topic><topic>Nipecotic Acids - chemistry</topic><topic>Peptides - chemistry</topic><topic>Proline - analogs & derivatives</topic><topic>Proline - chemistry</topic><topic>Protein Structure, Secondary</topic><topic>Pyrrolidines - chemistry</topic><topic>Spectrophotometry, Ultraviolet</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Huck, Bayard R</creatorcontrib><creatorcontrib>Langenhan, Joseph M</creatorcontrib><creatorcontrib>Gellman, Samuel H</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><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Huck, Bayard R</au><au>Langenhan, Joseph M</au><au>Gellman, Samuel H</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Non-Hydrogen-Bonded Secondary Structure in β-Peptides: Evidence from Circular Dichroism of (S)-Pyrrolidine-3- carboxylic Acid Oligomers and (S)-Nipecotic Acid Oligomers</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>1999-12-02</date><risdate>1999</risdate><volume>1</volume><issue>11</issue><spage>1717</spage><epage>1720</epage><pages>1717-1720</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>Homooligomers of β-amino acids (S)-3-pyrrolidine-3-carboxylic acid (PCA) and (S)-nipecotic acid (Nip) were studied by circular dichroism (CD) in methanol. In each series, a profound change in the far-UV CD spectrum was observed from monomer to tetramer, but little change was observed from tetramer to hexamer. A comparable pattern is observed in the CD spectra of short proline oligomers. We conclude that both PCA and Nip oligomers with ≥ four residues adopt a characteristic secondary structure.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>10836030</pmid><doi>10.1021/ol9909482</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 1999-12, Vol.1 (11), p.1717-1720 |
| issn | 1523-7060 1523-7052 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_69482109 |
| source | MEDLINE; American Chemical Society Journals |
| subjects | Chromatography, High Pressure Liquid Circular Dichroism Nipecotic Acids - chemistry Peptides - chemistry Proline - analogs & derivatives Proline - chemistry Protein Structure, Secondary Pyrrolidines - chemistry Spectrophotometry, Ultraviolet |
| title | Non-Hydrogen-Bonded Secondary Structure in β-Peptides: Evidence from Circular Dichroism of (S)-Pyrrolidine-3- carboxylic Acid Oligomers and (S)-Nipecotic Acid Oligomers |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-02T22%3A57%3A41IST&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=Non-Hydrogen-Bonded%20Secondary%20Structure%20in%20%CE%B2-Peptides:%E2%80%89%20Evidence%20from%20Circular%20Dichroism%20of%20(S)-Pyrrolidine-3-%20carboxylic%20Acid%20Oligomers%20and%20(S)-Nipecotic%20Acid%20Oligomers&rft.jtitle=Organic%20letters&rft.au=Huck,%20Bayard%20R&rft.date=1999-12-02&rft.volume=1&rft.issue=11&rft.spage=1717&rft.epage=1720&rft.pages=1717-1720&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/ol9909482&rft_dat=%3Cproquest_cross%3E69482109%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=69482109&rft_id=info:pmid/10836030&rfr_iscdi=true |