Peptide Backbone Directed Self-Assembly of Merocyanine Oligomers into Duplex Structures
© 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH..
The pseudopeptide backbone provided by N-(2-aminoethyl)-glycine oligomers with attached nucleobases has been widely utilized in peptide nucleic acids (PNAs) as DNA mimics. Here we demonstrate the suitability of this backbone for the formation of structurally defined dye stacks. Toward this goal a series of peptide merocyanine (PMC) dye oligomers connected to a N-(2-aminoethyl)-glycine backbone were prepared through peptide synthesis. Our concentration-, temperature- and solvent-dependent UV/Vis absorption studies show that under the control of dipole-dipole interactions, smaller-sized oligomers consisting of one, two or three dyes self-assemble into defined duplex structures containing two up to six chromophores. In contrast, upon further extension of the oligomer, the chosen peptide backbone cannot direct the formation of a defined duplex architecture anymore due to intramolecular aggregation between the dyes. For all aggregate species a moderate aggregation-induced emission enhancement is observed.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2022 |
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| Erschienen: |
2022 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:61 |
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| Enthalten in: |
Angewandte Chemie (International ed. in English) - 61(2022), 21 vom: 16. Mai, Seite e202200120 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Liu, Bin [VerfasserIn] |
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| Links: |
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| Anmerkungen: |
Date Completed 10.05.2022 Date Revised 27.08.2022 published: Print-Electronic Citation Status MEDLINE |
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| doi: |
10.1002/anie.202200120 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| 520 | |a © 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH. | ||
| 520 | |a The pseudopeptide backbone provided by N-(2-aminoethyl)-glycine oligomers with attached nucleobases has been widely utilized in peptide nucleic acids (PNAs) as DNA mimics. Here we demonstrate the suitability of this backbone for the formation of structurally defined dye stacks. Toward this goal a series of peptide merocyanine (PMC) dye oligomers connected to a N-(2-aminoethyl)-glycine backbone were prepared through peptide synthesis. Our concentration-, temperature- and solvent-dependent UV/Vis absorption studies show that under the control of dipole-dipole interactions, smaller-sized oligomers consisting of one, two or three dyes self-assemble into defined duplex structures containing two up to six chromophores. In contrast, upon further extension of the oligomer, the chosen peptide backbone cannot direct the formation of a defined duplex architecture anymore due to intramolecular aggregation between the dyes. For all aggregate species a moderate aggregation-induced emission enhancement is observed | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Research Support, Non-U.S. Gov't | |
| 650 | 4 | |a Dipole-Dipole Interaction | |
| 650 | 4 | |a Duplex Structure | |
| 650 | 4 | |a Dye Assembly | |
| 650 | 4 | |a Merocyanine | |
| 650 | 4 | |a Peptide Backbone | |
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| 650 | 7 | |a Coloring Agents |2 NLM | |
| 650 | 7 | |a Indoles |2 NLM | |
| 650 | 7 | |a Peptide Nucleic Acids |2 NLM | |
| 650 | 7 | |a Peptides |2 NLM | |
| 650 | 7 | |a merocyanine |2 NLM | |
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| 700 | 1 | |a Vonhausen, Yvonne |e verfasserin |4 aut | |
| 700 | 1 | |a Schulz, Alexander |e verfasserin |4 aut | |
| 700 | 1 | |a Höbartner, Claudia |e verfasserin |4 aut | |
| 700 | 1 | |a Würthner, Frank |e verfasserin |4 aut | |
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