Dextran derivatives III. Synthesis of esters of dextran with n-substituted amino acids by the mixed anhydride method and study of the conditions for eliminating the protective groups
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1. New methods for the O-aminoacylation of dextran (“polyglucin”) with mixed anhydrides of N-protected amino acids with benzenesulfonyl chloride, tosyl chloride, ethyl chloroformate, and phosphorus oxychloride have been proposed.
2. By these methods, and also by the method developed previously using dicyclohexylcarbodiimide, esters of dextran with N-tosylglycine, N-o-nitrophenylsulfenylglycine, N-benzyloxycarbonyl-ε-aminoenanthic acid, N-tert-butoxycarbonyl-L-alanine, N-tert-butoxycarbonyl-L-phenylalanine, N-o-nitrophenylsulfenyl-L-phenylalanine, and N-o-nitrophenylsulfenyl-L-valine have been synthesized.
3. Methods for eliminating the o-nitrophenylsulfenyl group from esters of NPS amino acids with dextran by means of thiophenol or a mixture of Na2S2O3 + KI have been recommended.
KeywordsDextran Protective Group Thiophenol Phosphorus Oxychloride Mixed Anhydride
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