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β-Peptides incorporating polyhydroxylated cyclohexane β-amino acid: synthesis and conformational study

Identificadores del recurso

Organic & Biomolecular Chemistry, 42

http://hdl.handle.net/10347/33219

10.1039/D3OB00906H

1477-0539

Origin

(Minerva. Repositorio Institucional da Universidade de Santiago de Compostela)

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Title:: β-Peptides incorporating polyhydroxylated cyclohexane β-amino acid: synthesis and conformational study
Description:: We describe the synthesis of trihydroxylated cyclohexane β-amino acids from (−)-shikimic acid, in their cis and trans configuration, and the incorporation of the trans isomer into a trans-2-aminocyclohexanecarboxylic acid peptide chain. Subsequently, the hydroxyl groups were partially or totally deprotected. The structural study of the new peptides by FTIR, CD, solution NMR and DFT calculations revealed that they all fold into a 14-helix secondary structure, similarly to the homooligomer of trans-2-aminocyclohexanecarboxylic acid. This means that the high degree of substitution of the cyclohexane ring of the new residue is compatible with the adoption of a stable helical secondary structure and opens opportunities for the design of more elaborate peptidic foldamers with oriented polar substituents at selected positions of the cycloalkane residues.; This work has received financial support from the Xunta de Galicia and the European Regional Development Fund- ERDF (ED431C 2018/30, ED431F 2020/05 and Centro singular de investigación de Galicia accreditation 2019-2022, ED431G 2019/ 03). Funding from the Agencia Estatal de Investigación (AEI) and the European Regional Development Fund- ERDF (RTI2018098795-A-I00 and PDC2022-133402-I00) is also acknowledged. R. G.-F. thanks Ministerio de Ciencia, Innovación y Universidades for a “Ramón y Cajal” contract (RYC-2016-20335). L. B. thanks Ministerio de Educación, Cultura y Deporte for a FPU fellowship (FPU13/01243). D. R. thanks Xunta de Galicia for a predoctoral fellowship. All calculations were carried out at the Centro de Supercomputación de Galicia (CESGA). Funding for open access charge: Universidade de Santiago de Compostela/CRUE.; SI
Idioma:: English
Autor/Productor:: Reza Ramos, David; Balo Becerra, Rosalino; Otero, José M.; Fletcher, Ai M.; García Fandiño, Rebeca; Sánchez-Pedregal, Víctor M.; Davies, Stephen G.; Estévez Cabanas, Ramón José; Estévez Cabanas, Juan Carlos
Publisher:: Royal Society of Chemistry
Otros colaboradores/productores:: Universidade de Santiago de Compostela. Centro de Investigación en Química Biolóxica e Materiais Moleculares; Universidade de Santiago de Compostela. Departamento de Química Orgánica
Rights:: Open access. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence; Atribución 4.0 Internacional; http://creativecommons.org/licenses/by/4.0/; open access
Date:: 2024-03-15T11:08:10Z; 2023
Tipo de recurso:: journal article; VoR

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1. <dc:title>β-Peptides incorporating polyhydroxylated cyclohexane β-amino acid: synthesis and conformational study</dc:title>
2. <dc:creator>Reza Ramos, David</dc:creator>
3. <dc:creator>Balo Becerra, Rosalino</dc:creator>
4. <dc:creator>Otero, José M.</dc:creator>
5. <dc:creator>Fletcher, Ai M.</dc:creator>
6. <dc:creator>García Fandiño, Rebeca</dc:creator>
7. <dc:creator>Sánchez-Pedregal, Víctor M.</dc:creator>
8. <dc:creator>Davies, Stephen G.</dc:creator>
9. <dc:creator>Estévez Cabanas, Ramón José</dc:creator>
10. <dc:creator>Estévez Cabanas, Juan Carlos</dc:creator>
11. <dc:contributor>Universidade de Santiago de Compostela. Centro de Investigación en Química Biolóxica e Materiais Moleculares</dc:contributor>
12. <dc:contributor>Universidade de Santiago de Compostela. Departamento de Química Orgánica</dc:contributor>
13. <dc:description>We describe the synthesis of trihydroxylated cyclohexane β-amino acids from (−)-shikimic acid, in their cis and trans configuration, and the incorporation of the trans isomer into a trans-2-aminocyclohexanecarboxylic acid peptide chain. Subsequently, the hydroxyl groups were partially or totally deprotected. The structural study of the new peptides by FTIR, CD, solution NMR and DFT calculations revealed that they all fold into a 14-helix secondary structure, similarly to the homooligomer of trans-2-aminocyclohexanecarboxylic acid. This means that the high degree of substitution of the cyclohexane ring of the new residue is compatible with the adoption of a stable helical secondary structure and opens opportunities for the design of more elaborate peptidic foldamers with oriented polar substituents at selected positions of the cycloalkane residues.</dc:description>
14. <dc:description>This work has received financial support from the Xunta de Galicia and the European Regional Development Fund- ERDF (ED431C 2018/30, ED431F 2020/05 and Centro singular de investigación de Galicia accreditation 2019-2022, ED431G 2019/ 03). Funding from the Agencia Estatal de Investigación (AEI) and the European Regional Development Fund- ERDF (RTI2018098795-A-I00 and PDC2022-133402-I00) is also acknowledged. R. G.-F. thanks Ministerio de Ciencia, Innovación y Universidades for a “Ramón y Cajal” contract (RYC-2016-20335). L. B. thanks Ministerio de Educación, Cultura y Deporte for a FPU fellowship (FPU13/01243). D. R. thanks Xunta de Galicia for a predoctoral fellowship. All calculations were carried out at the Centro de Supercomputación de Galicia (CESGA). Funding for open access charge: Universidade de Santiago de Compostela/CRUE.</dc:description>
15. <dc:description>SI</dc:description>
16. <dc:date>2024-03-15T11:08:10Z</dc:date>
17. <dc:date>2024-03-15T11:08:10Z</dc:date>
18. <dc:date>2023</dc:date>
19. <dc:type>journal article</dc:type>
20. <dc:type>VoR</dc:type>
21. <dc:identifier>Organic & Biomolecular Chemistry, 42</dc:identifier>
22. <dc:identifier>http://hdl.handle.net/10347/33219</dc:identifier>
23. <dc:identifier>10.1039/D3OB00906H</dc:identifier>
24. <dc:identifier>1477-0539</dc:identifier>
25. <dc:language>eng</dc:language>
26. <dc:rights>Open access. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence</dc:rights>
27. <dc:rights>Atribución 4.0 Internacional</dc:rights>
28. <dc:rights>http://creativecommons.org/licenses/by/4.0/</dc:rights>
29. <dc:rights>open access</dc:rights>
30. <dc:publisher>Royal Society of Chemistry</dc:publisher>
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