H-Bond Self-Assembly: Folding versus Duplex Formation.
Identifieur interne : 000C97 ( PubMed/Curation ); précédent : 000C96; suivant : 000C98H-Bond Self-Assembly: Folding versus Duplex Formation.
Auteurs : Diego Nú Ez-Villanueva [Royaume-Uni] ; Giulia Iadevaia [Royaume-Uni] ; Alexander E. Stross [Royaume-Uni] ; Michael A. Jinks [Royaume-Uni] ; Jonathan A. Swain [Royaume-Uni] ; Christopher A. Hunter [Royaume-Uni]Source :
- Journal of the American Chemical Society [ 1520-5126 ] ; 2017.
Abstract
Linear oligomers equipped with complementary H-bond donor (D) and acceptor (A) sites can interact via intermolecular H-bonds to form duplexes or fold via intramolecular H-bonds. These competing equilibria have been quantified using NMR titration and dilution experiments for seven systems featuring different recognition sites and backbones. For all seven architectures, duplex formation is observed for homo-sequence 2-mers (AA·DD) where there are no competing folding equilibria. The corresponding hetero-sequence AD 2-mers also form duplexes, but the observed self-association constants are strongly affected by folding equilibria in the monomeric states. When the backbone is flexible (five or more rotatable bonds separating the recognition sites), intramolecular H-bonding is favored, and the folded state is highly populated. For these systems, the stability of the AD·AD duplex is 1-2 orders of magnitude lower than that of the corresponding AA·DD duplex. However, for three architectures which have more rigid backbones (fewer than five rotatable bonds), intramolecular interactions are not observed, and folding does not compete with duplex formation. These systems are promising candidates for the development of longer, mixed-sequence synthetic information molecules that show sequence-selective duplex formation.
DOI: 10.1021/jacs.7b01357
PubMed: 28470070
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Stross</name><affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry, University of Cambridge , Lensfield Road, Cambridge CB2 1EW, U.K.</nlm:affiliation><country xml:lang="fr">Royaume-Uni</country><wicri:regionArea>Department of Chemistry, University of Cambridge , Lensfield Road, Cambridge CB2 1EW</wicri:regionArea></affiliation></author><author><name sortKey="Jinks, Michael A" sort="Jinks, Michael A" uniqKey="Jinks M" first="Michael A" last="Jinks">Michael A. Jinks</name><affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry, University of Cambridge , Lensfield Road, Cambridge CB2 1EW, U.K.</nlm:affiliation><country xml:lang="fr">Royaume-Uni</country><wicri:regionArea>Department of Chemistry, University of Cambridge , Lensfield Road, Cambridge CB2 1EW</wicri:regionArea></affiliation></author><author><name sortKey="Swain, Jonathan A" sort="Swain, Jonathan A" uniqKey="Swain J" first="Jonathan A" last="Swain">Jonathan A. Swain</name><affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry, University of Cambridge , Lensfield Road, Cambridge CB2 1EW, U.K.</nlm:affiliation><country xml:lang="fr">Royaume-Uni</country><wicri:regionArea>Department of Chemistry, University of Cambridge , Lensfield Road, Cambridge CB2 1EW</wicri:regionArea></affiliation></author><author><name sortKey="Hunter, Christopher A" sort="Hunter, Christopher A" uniqKey="Hunter C" first="Christopher A" last="Hunter">Christopher A. Hunter</name><affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry, University of Cambridge , Lensfield Road, Cambridge CB2 1EW, U.K.</nlm:affiliation><country xml:lang="fr">Royaume-Uni</country><wicri:regionArea>Department of Chemistry, University of Cambridge , Lensfield Road, Cambridge CB2 1EW</wicri:regionArea></affiliation></author></analytic><series><title level="j">Journal of the American Chemical Society</title><idno type="eISSN">1520-5126</idno><imprint><date when="2017" type="published">2017</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Linear oligomers equipped with complementary H-bond donor (D) and acceptor (A) sites can interact via intermolecular H-bonds to form duplexes or fold via intramolecular H-bonds. These competing equilibria have been quantified using NMR titration and dilution experiments for seven systems featuring different recognition sites and backbones. For all seven architectures, duplex formation is observed for homo-sequence 2-mers (AA·DD) where there are no competing folding equilibria. The corresponding hetero-sequence AD 2-mers also form duplexes, but the observed self-association constants are strongly affected by folding equilibria in the monomeric states. When the backbone is flexible (five or more rotatable bonds separating the recognition sites), intramolecular H-bonding is favored, and the folded state is highly populated. For these systems, the stability of the AD·AD duplex is 1-2 orders of magnitude lower than that of the corresponding AA·DD duplex. However, for three architectures which have more rigid backbones (fewer than five rotatable bonds), intramolecular interactions are not observed, and folding does not compete with duplex formation. These systems are promising candidates for the development of longer, mixed-sequence synthetic information molecules that show sequence-selective duplex formation.</div></front></TEI><pubmed><MedlineCitation Status="PubMed-not-MEDLINE" Owner="NLM"><PMID Version="1">28470070</PMID><DateCompleted><Year>2018</Year><Month>05</Month><Day>09</Day></DateCompleted><DateRevised><Year>2019</Year><Month>01</Month><Day>13</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1520-5126</ISSN><JournalIssue CitedMedium="Internet"><Volume>139</Volume><Issue>19</Issue><PubDate><Year>2017</Year><Month>05</Month><Day>17</Day></PubDate></JournalIssue><Title>Journal of the American Chemical Society</Title><ISOAbbreviation>J. Am. Chem. Soc.</ISOAbbreviation></Journal><ArticleTitle>H-Bond Self-Assembly: Folding versus Duplex Formation.</ArticleTitle><Pagination><MedlinePgn>6654-6662</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1021/jacs.7b01357</ELocationID><Abstract><AbstractText>Linear oligomers equipped with complementary H-bond donor (D) and acceptor (A) sites can interact via intermolecular H-bonds to form duplexes or fold via intramolecular H-bonds. These competing equilibria have been quantified using NMR titration and dilution experiments for seven systems featuring different recognition sites and backbones. For all seven architectures, duplex formation is observed for homo-sequence 2-mers (AA·DD) where there are no competing folding equilibria. The corresponding hetero-sequence AD 2-mers also form duplexes, but the observed self-association constants are strongly affected by folding equilibria in the monomeric states. When the backbone is flexible (five or more rotatable bonds separating the recognition sites), intramolecular H-bonding is favored, and the folded state is highly populated. For these systems, the stability of the AD·AD duplex is 1-2 orders of magnitude lower than that of the corresponding AA·DD duplex. However, for three architectures which have more rigid backbones (fewer than five rotatable bonds), intramolecular interactions are not observed, and folding does not compete with duplex formation. These systems are promising candidates for the development of longer, mixed-sequence synthetic information molecules that show sequence-selective duplex formation.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Núñez-Villanueva</LastName><ForeName>Diego</ForeName><Initials>D</Initials><Identifier Source="ORCID">0000-0002-1005-1464</Identifier><AffiliationInfo><Affiliation>Department of Chemistry, University of Cambridge , Lensfield Road, Cambridge CB2 1EW, U.K.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Iadevaia</LastName><ForeName>Giulia</ForeName><Initials>G</Initials><AffiliationInfo><Affiliation>Department of Chemistry, University of Cambridge , Lensfield Road, Cambridge CB2 1EW, U.K.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Stross</LastName><ForeName>Alexander E</ForeName><Initials>AE</Initials><AffiliationInfo><Affiliation>Department of Chemistry, University of Cambridge , Lensfield Road, Cambridge CB2 1EW, U.K.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Jinks</LastName><ForeName>Michael A</ForeName><Initials>MA</Initials><AffiliationInfo><Affiliation>Department of Chemistry, University of Cambridge , Lensfield Road, Cambridge CB2 1EW, U.K.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Swain</LastName><ForeName>Jonathan A</ForeName><Initials>JA</Initials><AffiliationInfo><Affiliation>Department of Chemistry, University of Cambridge , Lensfield Road, Cambridge CB2 1EW, U.K.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Hunter</LastName><ForeName>Christopher A</ForeName><Initials>CA</Initials><Identifier Source="ORCID">0000-0002-5182-1859</Identifier><AffiliationInfo><Affiliation>Department of Chemistry, University of Cambridge , Lensfield Road, Cambridge CB2 1EW, U.K.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><GrantList 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