Abstract
In the title compound, the de-hydro-dipeptide (Boc-Phe-ΔAla-OiPr, C20H28N2O5), the mol-ecule has a trans conformation of the N-methyl-amide group. The geometry of the de-hydro-alanine moiety is to some extent different from those usually found in simple peptides, indicating conjugation between the H2C=C group and the peptide bond. The bond angles around de-hydro-alanine have unusually high values due to the steric hindrance, the same inter-action influencing the slight distortion from planarity of the de-hydro-alanine. The mol-ecule is stabilized by intra-molecular inter-actions between the isopropyl group and the N atoms of the peptide main chain. In the crystal, an N-H⋯O hydrogen bond links the mol-ecules into ribbons, giving a herringbone head-to-head packing arrangement extending along the [100] direction. In the stacks, the mol-ecules are linked by weak C-H⋯O hydrogen-bonding associations.
Highlights
Faculty of Chemistry, University of Opole, Oleska 48, 45-052 Opole, Poland. *Correspondence e-mail: In the title compound, the dehydrodipeptide (Boc–Phe–Ala–OiPr, C20H28N2O5), the molecule has a trans conformation of the N-methylamide group
The geometry of the dehydroalanine moiety is to some extent different from those usually found in simple peptides, indicating conjugation between the
The bond angles around dehydroalanine have unusually high values due to the steric hindrance, the same interaction influencing the slight distortion from planarity of the dehydroalanine
Summary
Dehydropeptides are a class of compounds containing at least one residue of an ,-dehydroamino acid. These compounds are of interest in many fields of science because of their structural and chemical properties. The development of synthetic methods for dehydropeptide preparation has resulted in a search for practical applications for these compounds. Compounds containing dehydroamino acid residues are considered to be inhibitors of enzymes (Makowski et al, 2001; Latajka et al, 2006, 2008). They are more resistant towards proteolytic enzymes than saturated analogues. The preparation of the title compound, N-(tert-butoxycarbonyl)-phenylalanyldehydroalanine isopropyl ester and its structure determination by single-crystal X-ray crystallographic methods are presented
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Free) 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a call
