Absolute handedness control of oligoamide double helices by chiral oxazolylaniline induction
Aromatic oligoamide double helices bearing a chiral oxazolylaniline moiety at the C-terminus were synthesized and their helix handedness was completely controlled (de > 99%). The absolute helix sense and the de values were evaluated by using 1 H NMR, X-ray crystallography, and circular dichroism...
Gespeichert in:
| Veröffentlicht in: | Organic & biomolecular chemistry 2020-09, Vol.18 (34), p.6643-665 |
|---|---|
| Hauptverfasser: | , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 665 |
|---|---|
| container_issue | 34 |
| container_start_page | 6643 |
| container_title | Organic & biomolecular chemistry |
| container_volume | 18 |
| creator | Yang, Ling Ma, Chunmiao Kauffmann, Brice Li, Dongyao Gan, Quan |
| description | Aromatic oligoamide double helices bearing a chiral oxazolylaniline moiety at the C-terminus were synthesized and their helix handedness was completely controlled (de > 99%). The absolute helix sense and the de values were evaluated by using
1
H NMR, X-ray crystallography, and circular dichroism (CD). Using crystal structure analysis, the high efficiency of helix handedness induction was attributed to the close location of the asymmetric carbon center to the helix orbits
via
intramolecular hydrogen bonding. The CD experiments also showed that there is no loss of chiral induction either in the interconversion of single and double helices or by elongation of the sequences.
Aromatic oligoamide double helices bearing a chiral oxazolylaniline moiety were synthesized and their helix handedness was completely controlled (de > 99%). |
| doi_str_mv | 10.1039/d0ob01503b |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1039_D0OB01503B</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2439182900</sourcerecordid><originalsourceid>FETCH-LOGICAL-c429t-2c36164c473db2ebc4386a92418a67d17f84a9a208f5dcf742e03b8fbf65ad0b3</originalsourceid><addsrcrecordid>eNp90UlLAzEYBuAginW7eFdGvIgwmm2WHNu6gtCL3oQhq6akk5rMgPXXG22t4MFTAu_Dx5c3ABwieIEgYZcKegFRAYnYADuIVlUOC8I213cMB2A3ximEiFUl3QYDgmuMaoZ3wPNQRO_6TmevvFVatTrGTPq2C95l3mTe2RfPZ1bpTPleuOS0s1LHTCwy-WoDT-ydf3i3cLy1zrY6s63qZWd9uw-2DHdRH6zOPfB0c_04vssfJrf34-FDLilmXY4lKVFJJa2IElgLSUldcoYpqnlZKVSZmnLGMaxNoaSpKNbprbURpiy4goLsgbPl3Hnwb72OXTOzUWqXNtK-jw2mpCSM4LJI9PQPnfo-tGm7L8VQjRmESZ0vlQw-xqBNMw92xsOiQbD56ry5gpPRd-ejhI9XI3sx02pNf0pO4GgJQpTr9PfTUn7yX97MlSGfwPWR2w</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2439182900</pqid></control><display><type>article</type><title>Absolute handedness control of oligoamide double helices by chiral oxazolylaniline induction</title><source>Royal Society Of Chemistry Journals 2008-</source><source>Alma/SFX Local Collection</source><creator>Yang, Ling ; Ma, Chunmiao ; Kauffmann, Brice ; Li, Dongyao ; Gan, Quan</creator><creatorcontrib>Yang, Ling ; Ma, Chunmiao ; Kauffmann, Brice ; Li, Dongyao ; Gan, Quan</creatorcontrib><description>Aromatic oligoamide double helices bearing a chiral oxazolylaniline moiety at the C-terminus were synthesized and their helix handedness was completely controlled (de > 99%). The absolute helix sense and the de values were evaluated by using
1
H NMR, X-ray crystallography, and circular dichroism (CD). Using crystal structure analysis, the high efficiency of helix handedness induction was attributed to the close location of the asymmetric carbon center to the helix orbits
via
intramolecular hydrogen bonding. The CD experiments also showed that there is no loss of chiral induction either in the interconversion of single and double helices or by elongation of the sequences.
Aromatic oligoamide double helices bearing a chiral oxazolylaniline moiety were synthesized and their helix handedness was completely controlled (de > 99%).</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/d0ob01503b</identifier><identifier>PMID: 32821892</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>C-Terminus ; Circular dichroism ; Crystal structure ; Crystallography ; Crystals ; Dichroism ; Elongation ; Handedness ; Helices ; Hydrogen bonding ; NMR ; Nuclear magnetic resonance ; Structural analysis ; X-ray crystallography</subject><ispartof>Organic & biomolecular chemistry, 2020-09, Vol.18 (34), p.6643-665</ispartof><rights>Copyright Royal Society of Chemistry 2020</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c429t-2c36164c473db2ebc4386a92418a67d17f84a9a208f5dcf742e03b8fbf65ad0b3</citedby><cites>FETCH-LOGICAL-c429t-2c36164c473db2ebc4386a92418a67d17f84a9a208f5dcf742e03b8fbf65ad0b3</cites><orcidid>0000-0003-4612-2268 ; 0000-0002-2932-3255</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,778,782,27907,27908</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/32821892$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Yang, Ling</creatorcontrib><creatorcontrib>Ma, Chunmiao</creatorcontrib><creatorcontrib>Kauffmann, Brice</creatorcontrib><creatorcontrib>Li, Dongyao</creatorcontrib><creatorcontrib>Gan, Quan</creatorcontrib><title>Absolute handedness control of oligoamide double helices by chiral oxazolylaniline induction</title><title>Organic & biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><description>Aromatic oligoamide double helices bearing a chiral oxazolylaniline moiety at the C-terminus were synthesized and their helix handedness was completely controlled (de > 99%). The absolute helix sense and the de values were evaluated by using
1
H NMR, X-ray crystallography, and circular dichroism (CD). Using crystal structure analysis, the high efficiency of helix handedness induction was attributed to the close location of the asymmetric carbon center to the helix orbits
via
intramolecular hydrogen bonding. The CD experiments also showed that there is no loss of chiral induction either in the interconversion of single and double helices or by elongation of the sequences.
Aromatic oligoamide double helices bearing a chiral oxazolylaniline moiety were synthesized and their helix handedness was completely controlled (de > 99%).</description><subject>C-Terminus</subject><subject>Circular dichroism</subject><subject>Crystal structure</subject><subject>Crystallography</subject><subject>Crystals</subject><subject>Dichroism</subject><subject>Elongation</subject><subject>Handedness</subject><subject>Helices</subject><subject>Hydrogen bonding</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Structural analysis</subject><subject>X-ray crystallography</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp90UlLAzEYBuAginW7eFdGvIgwmm2WHNu6gtCL3oQhq6akk5rMgPXXG22t4MFTAu_Dx5c3ABwieIEgYZcKegFRAYnYADuIVlUOC8I213cMB2A3ximEiFUl3QYDgmuMaoZ3wPNQRO_6TmevvFVatTrGTPq2C95l3mTe2RfPZ1bpTPleuOS0s1LHTCwy-WoDT-ydf3i3cLy1zrY6s63qZWd9uw-2DHdRH6zOPfB0c_04vssfJrf34-FDLilmXY4lKVFJJa2IElgLSUldcoYpqnlZKVSZmnLGMaxNoaSpKNbprbURpiy4goLsgbPl3Hnwb72OXTOzUWqXNtK-jw2mpCSM4LJI9PQPnfo-tGm7L8VQjRmESZ0vlQw-xqBNMw92xsOiQbD56ry5gpPRd-ejhI9XI3sx02pNf0pO4GgJQpTr9PfTUn7yX97MlSGfwPWR2w</recordid><startdate>20200914</startdate><enddate>20200914</enddate><creator>Yang, Ling</creator><creator>Ma, Chunmiao</creator><creator>Kauffmann, Brice</creator><creator>Li, Dongyao</creator><creator>Gan, Quan</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7T7</scope><scope>7TM</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-4612-2268</orcidid><orcidid>https://orcid.org/0000-0002-2932-3255</orcidid></search><sort><creationdate>20200914</creationdate><title>Absolute handedness control of oligoamide double helices by chiral oxazolylaniline induction</title><author>Yang, Ling ; Ma, Chunmiao ; Kauffmann, Brice ; Li, Dongyao ; Gan, Quan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c429t-2c36164c473db2ebc4386a92418a67d17f84a9a208f5dcf742e03b8fbf65ad0b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>C-Terminus</topic><topic>Circular dichroism</topic><topic>Crystal structure</topic><topic>Crystallography</topic><topic>Crystals</topic><topic>Dichroism</topic><topic>Elongation</topic><topic>Handedness</topic><topic>Helices</topic><topic>Hydrogen bonding</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Structural analysis</topic><topic>X-ray crystallography</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yang, Ling</creatorcontrib><creatorcontrib>Ma, Chunmiao</creatorcontrib><creatorcontrib>Kauffmann, Brice</creatorcontrib><creatorcontrib>Li, Dongyao</creatorcontrib><creatorcontrib>Gan, Quan</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yang, Ling</au><au>Ma, Chunmiao</au><au>Kauffmann, Brice</au><au>Li, Dongyao</au><au>Gan, Quan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Absolute handedness control of oligoamide double helices by chiral oxazolylaniline induction</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2020-09-14</date><risdate>2020</risdate><volume>18</volume><issue>34</issue><spage>6643</spage><epage>665</epage><pages>6643-665</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>Aromatic oligoamide double helices bearing a chiral oxazolylaniline moiety at the C-terminus were synthesized and their helix handedness was completely controlled (de > 99%). The absolute helix sense and the de values were evaluated by using
1
H NMR, X-ray crystallography, and circular dichroism (CD). Using crystal structure analysis, the high efficiency of helix handedness induction was attributed to the close location of the asymmetric carbon center to the helix orbits
via
intramolecular hydrogen bonding. The CD experiments also showed that there is no loss of chiral induction either in the interconversion of single and double helices or by elongation of the sequences.
Aromatic oligoamide double helices bearing a chiral oxazolylaniline moiety were synthesized and their helix handedness was completely controlled (de > 99%).</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>32821892</pmid><doi>10.1039/d0ob01503b</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0003-4612-2268</orcidid><orcidid>https://orcid.org/0000-0002-2932-3255</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1477-0520 |
| ispartof | Organic & biomolecular chemistry, 2020-09, Vol.18 (34), p.6643-665 |
| issn | 1477-0520 1477-0539 |
| language | eng |
| recordid | cdi_crossref_primary_10_1039_D0OB01503B |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | C-Terminus Circular dichroism Crystal structure Crystallography Crystals Dichroism Elongation Handedness Helices Hydrogen bonding NMR Nuclear magnetic resonance Structural analysis X-ray crystallography |
| title | Absolute handedness control of oligoamide double helices by chiral oxazolylaniline induction |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-16T20%3A33%3A37IST&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=Absolute%20handedness%20control%20of%20oligoamide%20double%20helices%20by%20chiral%20oxazolylaniline%20induction&rft.jtitle=Organic%20&%20biomolecular%20chemistry&rft.au=Yang,%20Ling&rft.date=2020-09-14&rft.volume=18&rft.issue=34&rft.spage=6643&rft.epage=665&rft.pages=6643-665&rft.issn=1477-0520&rft.eissn=1477-0539&rft_id=info:doi/10.1039/d0ob01503b&rft_dat=%3Cproquest_cross%3E2439182900%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=2439182900&rft_id=info:pmid/32821892&rfr_iscdi=true |