アリールグリシジルエーテルで処理した絹および羊毛のガスクロマトグラフィーによる分析

抄録

Silk and wool fibers were treated with phenyl glycidyl ether (PGE) or p-tolyl glycidyl ether (TGE) in the presence of aqueous neutral salt according to Shiozaki and Tanaka, and the gas-liquid chromatography (GC) of the hydrolysates of the treated silk and wool fibers were studied for the identification and quantification of the artifact amino acids produced. The GC analysis was carried out by the linear temperature-programmed method on OV-17 and on Dexsil 300 GC columns, after the amino acids in the hydrolysate being converted to n-butyl esters of N-trifluoroacetyl (BTFA) derivatives. The peaks of O-(2-hydroxy-3-phenoxypropyl)tyrosine (PGE-TYR) and O-(2-hydroxy-3-p-tolyloxypropyl)tyrosine (TGE-TYR), which were not detected with a conventional automatic amino acid analyzer, were observed in the gas chromatograms of the silk and wool fibers treated with, PGE and TGE, respectively, and the Kováts retention indices of these peaks were determined. The Δ I values of PGE-TYR and TGE-TYR were about equal to each other and much higher than those of O-2-hydroxypropyltyrosine and O-2-hydroxybutyltyrosine, previously reported. The retention indices of TGE-TYR were the highest among those of amino acids ever reported. The GC analysis of the PGE-and TGE-treated wool fibers also indicated that 2, 3-dihydroxypropyl phenyl ether and 2, 3-dihydroxypropyl p-tolyl ether were present in their acid hydrolysates, respectively. This finding clearly demonstrates that, in addition to the tyrosine residues, the acidic amino acid residues in wool react with aryl glycidyl ethers.