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- W2045852270 endingPage "9191" @default.
- W2045852270 startingPage "9191" @default.
- W2045852270 abstract "C-linked carbo-β2-amino acids (β2-Caa), a new class of β-amino acid with a carbohydrate side chain having D-xylo configuration, were prepared from D-glucose. The main idea behind the design of the new β-amino acids was to move the steric strain of the bulky carbohydrate side chain from the Cβ- to the Cα-carbon atom and to explore its influence on the folding propensities in peptides with alternating (R)- and (S)-β2-Caas. The tetra- and hexapeptides derived were studied employing NMR (in CDCl3), CD, and molecular dynamics simulations. The β2-peptides of the present study form left-handed 12/10- and 10/12-mixed helices independent of the order of the alternating chiral amino acids in the sequence and result in a new motif. These results differ from earlier findings on β3-peptides of the same design, containing a carbohydrate side chain with D-xylo configuration, which form exclusively right-handed 12/10-mixed helices. Quantum chemical calculations employing ab initio MO theory suggest the side chain chirality as an important factor for the observed definite left- or right-handedness of the helices in the β2- and β3-peptides." @default.
- W2045852270 created "2016-06-24" @default.
- W2045852270 creator A5002172866 @default.
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- W2045852270 creator A5072453302 @default.
- W2045852270 creator A5089523135 @default.
- W2045852270 date "2012-01-01" @default.
- W2045852270 modified "2023-10-14" @default.
- W2045852270 title "Synthesis of C-linked carbo-β2-amino acids and β2-peptides: design of new motifs for left-handed 12/10- and 10/12-mixed helices" @default.
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- W2045852270 doi "https://doi.org/10.1039/c2ob26615f" @default.
- W2045852270 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/23089875" @default.
- W2045852270 hasPublicationYear "2012" @default.