Studies on spin-trapped radicals in. gamma. -irradiated aqueous solutions of cis-4-chloro-L-proline and cis-4-hydroxy-L-proline by high-performance liquid chromatography and ESR spectroscopy

Journal Article · Thu May 24 00:00:00 EDT 1984 · J. Phys. Chem.; (United States)

DOI:https://doi.org/10.1021/j150655a038· OSTI ID:6674237

Moriya, F; Makino, K; Iguchi, N; Suzuki, N; Rokushika, S; Hatano, H

Aqueous solutions of cis-4-chloro-L-proline and cis-4-hydroxy-L-proline were ..gamma.. irradiated in the presence of a spin trap, 2-methyl-2-nitrosopropane. Stable spin adducts produced in the ..gamma..-irradiated solutions were analyzed by high-performance liquid chromatography and ESR spectroscopy. The following spin adducts were found and identified: t-BuN(O)-*CH(COO/sup -/)-CH/sub 2/-*CHCl-CH/sub 2/NH/sub 3//sup +/ (I) and t-BuN(O)-*CHCH/sub 2/NH/sub 2//sup +/-*CH(COO/sup -/)CH/sub 2/ (II) from cis-4-chloro-L-proline (..gamma.. irradiated in the presence of sodium formate); t-BuN(O)-*CH(COO/sup -/)CH/sub 2/-*CH(OH)CH/sub 2/NH/sub 3//sup +/ (III) and t-BuN(O)-*CHNH/sub 2//sup +/-*CH(COO/sup -/)CH/sub 2/-*CHOH (IV) from cis-4-hydroxy-L-proline. Each of spin adducts II and IV was found as a pair of diastereomeric radicals, which revealed mutually different hyperfine splitting constants. The diastereoisomers of spin adduct II were individually separared, and their preferential conformations were considered on the basis of their hyperfine structures. The ESR spectra of the spin adducts from L-proline and trans-4-hydroxy-L-proline in their ..gamma..-irradiated aqueous systems, which have been reported previously (Suzuki et al., ref 1), were reexamined and assigned by computer simulations and by taking account of the results from cis-4-chloro-L-proline and cis-4-hydroxy-L-proline.

• Research Organization: Kyoto Univ., Japan
• OSTI ID: 6674237
• Journal Information: J. Phys. Chem.; (United States), Vol. 88:11
• Country of Publication: United States
• Language: English

Related Subjects

38 RADIATION CHEMISTRY, RADIOCHEMISTRY, AND NUCLEAR CHEMISTRY
HYDROXY COMPOUNDS
CHEMICAL RADIATION EFFECTS
ORGANIC CHLORINE COMPOUNDS
PROLINE
AQUEOUS SOLUTIONS
COMPUTERIZED SIMULATION
ELECTRON SPIN RESONANCE
EXPERIMENTAL DATA
GAMMA RADIATION
HYPERFINE STRUCTURE
ISOMERS
LIQUID COLUMN CHROMATOGRAPHY
NITROSO COMPOUNDS
PROPANE
RADICALS
SPECTRA
STEREOCHEMISTRY
STRUCTURAL CHEMICAL ANALYSIS
TRAPPING
ALKANES
AMINES
AMINO ACIDS
AZOLES
CARBOXYLIC ACIDS
CHEMISTRY
CHROMATOGRAPHY
DATA
DISPERSIONS
ELECTROMAGNETIC RADIATION
HETEROCYCLIC ACIDS
HETEROCYCLIC COMPOUNDS
HYDROCARBONS
INFORMATION
IONIZING RADIATIONS
MAGNETIC RESONANCE
MIXTURES
NUMERICAL DATA
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
PYRROLES
PYRROLIDINES
RADIATION CHEMISTRY
RADIATION EFFECTS
RADIATIONS
RESONANCE
SEPARATION PROCESSES
SIMULATION
SOLUTIONS
400600* - Radiation Chemistry