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Preparation of novel n 9 xanthyl alpha amino acid n carboxy anhydrides for use in peptide synthesis


, : Preparation of novel n 9 xanthyl alpha amino acid n carboxy anhydrides for use in peptide synthesis. Acta Chemica Scandinavica Series B Organic Chemistry & Biochemistry 33(9): 685-689

Xanthylation of .alpha.-amino acid N-carboxyanhydrides by xanthydrol in boiling toluene or acetic anhydride affords crystalline N-xanthyl N-carboxyanhydrides of high specific optical activity. Their reaction with aniline, amino acids, amino acid esters and peptides in organic and aqueous-organic media proceeded in good yield. A low level of racemization during coupling, combined with the facile removal of the xanthyl amino-protecting group by alcoholysis, makes N-xanthyl N-carboxyanhydrides useful derivatives for peptide synthesis.

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