Phosphinyl- and phosphinothioylamino acids and peptides. VI. The protection of the hydroxyl function in the tyrosine side-chain by the dimethylphosphinothioyl group.
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The use of the dimethylphosphinothioyl(Mpt) group for the protection of the hydroxyl function in the tyrosine side-chain was studied. <I>N</I>,<I>O</I>-Bis(Mpt)tyrosine was obtained directly by a Schotten-Baumann-type reaction of Mpt–Cl with tyrosine. The <I>O</I>-Mpt group was stable under acidic conditions, and it could be removed easily by alkaline hydrolysis or ester-exchange reaction. The usefulness of this new protecting group for the peptide synthesis was shown in the solid-phase synthesis of [D-Ala<SUP>2</SUP>, L-Leu<SUP>5</SUP>]-enkephalin(H–L-Tyr–D-Ala–Gly–L-Phe–L-Leu–OH) and its <I>N</I>-allyl derivative.
- 公益社団法人 日本化学会の論文
公益社団法人 日本化学会 | 論文
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