Polarity effects in 4-fluoro- and 4-(trifluoromethyl)prolines.
amino acids
cis–trans isomerism
fluorine
polarity
proline
Journal
Beilstein journal of organic chemistry
ISSN: 1860-5397
Titre abrégé: Beilstein J Org Chem
Pays: Germany
ID NLM: 101250746
Informations de publication
Date de publication:
2020
2020
Historique:
received:
18
05
2020
accepted:
06
07
2020
entrez:
9
8
2020
pubmed:
9
8
2020
medline:
9
8
2020
Statut:
epublish
Résumé
Fluorine-containing analogues of proline are valuable tools in engineering and NMR spectroscopic studies of peptides and proteins. Their use relies on the fundamental understanding of the interplay between the substituents and the main chain groups of the amino acid residue. This study aims to showcase the polarity-related effects that arise from the interaction between the functional groups in molecular models. Properties such as conformation, acid-base transition, and amide-bond isomerism were examined for diastereomeric 4-fluoroprolines, 4-(trifluoromethyl)prolines, and 1,1-difluoro-5-azaspiro[2.4]heptane-6-carboxylates. The preferred conformation on the proline ring originated from a preferential axial positioning for a single fluorine atom, and an equatorial positioning for a trifluoromethyl- or a difluoromethylene group. This orientation of the substituents explains the observed trends in the p
Identifiants
pubmed: 32765799
doi: 10.3762/bjoc.16.151
pmc: PMC7385359
doi:
Types de publication
Journal Article
Langues
eng
Pagination
1837-1852Informations de copyright
Copyright © 2020, Kubyshkin; licensee Beilstein-Institut.
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