Phosphinyl- and phosphinothioylamino acids and peptides. IV. Further examples of use of the diphenylphosphinothioyl group for the protection of amino acids.
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概要
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The preparation and purification of diphenylphosphinothioyl(Ppt)-amino acids were studied. The side-chain functional groups of tyrosine and cysteine were found to react also with diphenylphosphinothioyl chloride to form <I>O</I>-Ppt and <I>S</I>-Ppt derivatives. Acidic reagents for the removal of <I>N</I>-Ppt group were examined by using <I>N</I>,<I>O</I>-bis-Ppt-tyrosine ethyl ester (III) as the most difficult model, HCl in HCO<SUB>2</SUB>H–CH<SUB>2</SUB>Cl<SUB>2</SUB> being found to be most preferable. The <I>O</I>- and <I>S</I>-Ppt bonds were stable during the course of acidic treatments, but could be removed by alkaline hydrolysis. An application of Ppt-amino acids to the solid phase peptide synthesis is given.
- 公益社団法人 日本化学会の論文
著者
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IKEDA Shigeru
Department of Computer and Mathematical Sciences, Graduate School of Information Sciences, Tohoku Un
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Ueki Masaaki
Department of Anesthesia, Nishiwaki Municipal Hospital:Department of Anesthesia and Perioperative Medicine, Kobe University
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SHINOZAKI Kozo
Department of Applied Chemistry, Science University of Tokyo
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Shikano Etsuro
Department of Chemistry, Science University of Tokyo
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Tonegawa Fumio
Department of Chemistry, Science University of Tokyo
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Ueki Masaaki
Department of Chemistry, Science University of Tokyo
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