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Chiral 1,5-disubsti...
Chiral 1,5-disubstituted 1,2,3-triazoles-versatile tools for foldamers and peptidomimetic applications
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- Said Stålsmeden, Anna, 1983 (author)
- Chalmers tekniska högskola,Chalmers University of Technology
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- Paterson, Andrew, 1988 (author)
- Chalmers tekniska högskola,Chalmers University of Technology
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- Szigyártó, Imola Cs (author)
- Magyar Tudomanyos Akademia,Hungarian Academy of Sciences
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- Thunberg, Linda (author)
- AstraZeneca AB
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- Johansson, Johan, 1980 (author)
- AstraZeneca AB
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- Beke-Somfai, Tamas, 1977 (author)
- Magyar Tudomanyos Akademia,Hungarian Academy of Sciences
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- Kann, Nina, 1964 (author)
- Chalmers tekniska högskola,Chalmers University of Technology
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(creator_code:org_t)
- 2020
- 2020
- English.
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In: Organic and Biomolecular Chemistry. - : Royal Society of Chemistry (RSC). - 1477-0539 .- 1477-0520. ; 18:10, s. 1957-1967
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https://doi.org/10.1...
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Abstract
Subject headings
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- 1,4- A nd 1,5-Disubstituted triazole amino acid monomers have gained increasing interest among peptidic foldamers, as they are easily prepared via Cu- A nd Ru-catalyzed click reactions, with the potential for side chain variation. While the latter is key to their applicability, the synthesis and structural properties of the chiral mono-or disubstituted triazole amino acids have only been partially addressed. We here present the synthesis of all eight possible chiral derivatives of a triazole monomer prepared via a ruthenium-catalyzed azide alkyne cycloaddition (RuAAC). To evaluate the conformational properties of the individual building units, a systematic quantum chemical study was performed on all monomers, indicating their capacity to form several low energy conformers. This feature may be used to effect structural diversity when the monomers are inserted into various peptide sequences. We envisage that these results will facilitate new applications for these artificial oligomeric compounds in diverse areas, ranging from pharmaceutics to biotechnology.
Subject headings
- NATURVETENSKAP -- Kemi -- Polymerkemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Polymer Chemistry (hsv//eng)
- TEKNIK OCH TEKNOLOGIER -- Kemiteknik -- Polymerteknologi (hsv//swe)
- ENGINEERING AND TECHNOLOGY -- Chemical Engineering -- Polymer Technologies (hsv//eng)
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
Publication and Content Type
- art (subject category)
- ref (subject category)
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