6533b82cfe1ef96bd128fe5d

RESEARCH PRODUCT

Molecular and crystal structure of Nα-(9-fluorenyl)-methoxycarbonyl-L-ornithine hydrochloride diethyl ether solvate

Elzbieta MasiukiewiczLiliana MazurBarbara RzeszotarskaAnna E. Koziol

subject

HydrochlorideHydrogen bondStereochemistryL-OrnithineBioengineeringCrystal structureOrnithineBiochemistryMedicinal chemistryAnalytical Chemistrychemistry.chemical_compoundchemistryDrug DiscoverySide chainMolecular MedicineMoleculeDiethyl ether

description

The solid-state conformation of the first N-protected ornithine derivative has been established by X-ray analysis. The hydrochloride of Nα-(9-fluorenyl)methoxycarbonyl-l-ornithine crystallises as diethyl ether solvate. The backbone (ω0 ϕ, ψ χ1) torsion angles are (174.9°,–84.0°, 145.9°,–171.0°). The conformation of the urethane amide bonds istrans. The ornithine aliphatic side chain adopts preferred fully extended conformation which is stabilised by the hydrogen bonding of the-NH3+ group to the diethyl ether molecule, carboxyl group and Cl− anions.

https://doi.org/10.1007/bf02447550