Impact of the ΔPhe configuration on the Boc-Gly-ΔPhe-NHMe conformation: experiment and theory

Conformational propensities of N - t -butoxycarbonyl-glycine-( E/Z )-dehydrophenylalanine N′ -methylamides (Boc-Gly-( E/Z )-ΔPhe-NHMe) in chloroform were investigated by NMR and IR techniques. The low-temperature crystal structure of the E isomer was determined by single crystal X-ray diffraction an...

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Published in:Structural chemistry 2019-10, Vol.30 (5), p.1685-1697
Main Authors: Buczek, Aneta, Siodłak, Dawid, Bujak, Maciej, Makowski, Maciej, Kupka, Teobald, Broda, Małgorzata A.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Chloroform
Computer Applications in Chemistry
Configurations
Crystal structure
Crystals
Glycine
Isomers
NMR
Nuclear magnetic resonance
Original Research
Physical Chemistry
Single crystals
Theoretical and Computational Chemistry
Vapor phases
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Summary:Conformational propensities of N - t -butoxycarbonyl-glycine-( E/Z )-dehydrophenylalanine N′ -methylamides (Boc-Gly-( E/Z )-ΔPhe-NHMe) in chloroform were investigated by NMR and IR techniques. The low-temperature crystal structure of the E isomer was determined by single crystal X-ray diffraction and the experimental data were elaborated by theoretical calculations using DFT (B3LYP, M06-2X) and MP2 approaches. The β-turn tendencies for both isomers were determined in the gas phase and in the presence of solvent. The obtained results reveal that the configuration of ΔPhe residue significantly affects the conformations of the studied dehydropeptides. The tendency to adopt β-turn conformations is significantly lower for the E isomer (Boc-Gly-( E )-ΔPhe-NHMe), both in gas phase and in chloroform solution.
ISSN:1040-0400
1572-9001
DOI:10.1007/s11224-019-01387-w