NDLI: Conformational preferences in the β-peptide oligomers of cis-2-amino-1-fluorocyclobutane-1-carboxylic acid

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Conformational preferences in the β-peptide oligomers of cis-2-amino-1-fluorocyclobutane-1-carboxylic acid

Content Provider	Semantic Scholar
Author	Hassoun, Ammar Grison, Claire M. Guillot, Régis Boddaert, Thomas Aitken, David J.
Copyright Year	2015
Abstract	An efficient synthesis of cis-2-amino-1-fluorocyclobutane-1-carboxylic acid in single enantiomer form was established and protected homo-oligomers (2-, 4-, and 6-mers) of this cyclic cis-β-amino acid were prepared. Conformational analysis of these oligomers using IR, NMR and CD techniques in solution, supported by molecular modelling studies, suggested a strong conformational preference for a well-defined strand-like structure in which intra-residue hydrogen bonding is weak at best and is not consequential for adoption of the secondary structure. Single crystal X-ray analysis of the tetramer showed that a regular strand-like conformation is adopted in the solid state; only intermolecular hydrogen bonding networks are observed. The backbone topology and the 4-membered ring orientations are noticeably different from those of the tetramer of the corresponding non-fluorinated cis-β-amino acid.
Starting Page	3270
Ending Page	3279
Page Count	10
File Format	PDF HTM / HTML
DOI	10.1039/C4NJ01929F
Volume Number	39
Alternate Webpage(s)	https://pubs.rsc.org/en/content/getauthorversionpdf/C4NJ01929F
Alternate Webpage(s)	http://www.rsc.org/suppdata/nj/c4/c4nj01929f/c4nj01929f1.pdf
Alternate Webpage(s)	https://doi.org/10.1039/C4NJ01929F
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article

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