RT Journal Article
T1 β-Peptides incorporating polyhydroxylated cyclohexane β-amino acid: synthesis and conformational study
A1 Reza Ramos, David
A1 Balo Becerra, Rosalino
A1 Otero, José M.
A1 Fletcher, Ai M.
A1 García Fandiño, Rebeca
A1 Sánchez Pedregal, Víctor Manuel
A1 Davies, Stephen G.
A1 Estévez Cabanas, Ramón José
A1 Estévez Cabanas, Juan Carlos
AB 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.
PB Royal Society of Chemistry
YR 2023
FD 2023
LK http://hdl.handle.net/10347/33219
UL http://hdl.handle.net/10347/33219
LA eng
NO Organic & Biomolecular Chemistry, 42
NO 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.
DS Minerva
RD 27 abr 2026