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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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Related references

Katakai, R., 1975: Peptide synthesis using o-nitrophenylsulfenyl N-carboxy alpha-amino acid anhydrides. Journal of Organic Chemistry 40(19): 2697-2702

Kircher, K.; Zahn, H.; Berndt, H., 1980: Peptides 119. peptide synthesis with n carboxy alpha amino acid anhydrides. On reaction of N-carboxy-.alpha.-amino acid anhydrides (NCA) with equimolar amounts of amino acids or excess NCA in potassium borate buffer of pH 10.2 (0.degree. C) considerable amounts of homooligomers and homopolymers are formed. If an excess of...

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Wilder R.; Mobashery S., 1992: The use of triphosgene in preparation of n carboxy alpha amino acid anhydrides. Journal of Organic Chemistry 57(9): 2755-2756

Halstrom J.; Kovacs K., 1987: Improved preparation of crystalline n 9 xanthyl amino acid n carboxyanhydrides for peptide synthesis. Theodoropoulos, D (Ed ) Peptides, 1986; 19th European Symposium, Chalkidiki, Greece, August 31-September 5, 1986 Xix+684p Walter De Gruyter: Berlin, West Germany; New York, New York, Usa Illus 111-114

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