6533b7cefe1ef96bd1257a04

RESEARCH PRODUCT

N-[Glycyl-(Z)-α,β-dehydrophenylalanylglycyl-(Z)-α,β-dehydrophenylalanyl]glycine trifluoroacetate methanol solvate

Maciej MakowskiIwona MikołajczykMarek LisowskiTadeusz Lis

subject

chemistry.chemical_classificationResidue (chemistry)chemistryHydrogen bondStereochemistryGeneral Materials SciencePeptideGeneral ChemistryCondensed Matter Physics

description

The mol­ecular conformation of the title dehydro­peptide, H+-Gly1–ΔZPhe2–Gly3–ΔZPhe4–Gly5-OH·CF3COO−·CH3OH or C24H26N5O6+·CF3COO−·CH3OH, is characterized by the presence of two intra­molecular N—H⋯O hydrogen bonds that stabilize two type III β-turns, at the ΔZPhe2 (ΔZPhe is the Z isomer of the α,β-dehydro­phenyl­alanine residue) and Gly3, and Gly3 and ΔZPhe4 residues. As a result, the penta­peptide adopts a right-handed 310-helical conformation. All peptide units are linked trans to each other.

https://doi.org/10.1107/s1600536807016613