B. P. Gottikh

A new method of synthesizing 3′(2′)-O-aminoacylnucleosides and nucleotides

1. A new method of synthesizing 3′- and 2′-O-aminoacylnucleosides and aminoeylnucleotides based on the activation of N-substituted amino acids with imidazole was developed. 2. In using this method, it is most convenient to use the o-nitrophenylsulfenyl protection for the amino acid when preparing O-aminoacylnueleosides, and the tert-butyloxycarbonyl group in the case of 5′-nucleotides.

Aminoacyl derivatives of nucleosides, nucleotides, and polynucleotides: Communication 14. Aminoacylation of oligonucleotides that enter into the composition of the acceptor end of tRNA

1. The method of synthesis of 3′(2′)-O-aminoacylnucleotides, based on the interaction of nucleoside-5′-phosphates with imidazolides of N-protecting amino acids and subsequent removal of N-protecting group, was extended to the preparation of the appropriate peptidylnucleotides. 2. The synthesis of 3′(2′)-O-alanyl-alanyl- and 3′(2′)-O-leucyl-glycyl-tryptophanyl-nucleoside-5′-phosphate was realized for all four basic types of nucleotides (adenylic, guanylic, cytidylic, and uridylic acids).

New method for the synthesis of 3′(2′)-o-aminoacyl-adenosine

A new method was developed for the synthesis of a 3′(2′)-O-aminoacyl-adenosine by the condensation of N-protonated amino acids with 5′-O-trityladenosine in the presence of carbonyldiimidazole, with subsequent removal of the trityl protection.

Aminoacyl derivatives of nucleosides, nucleotides, and polynucleotides Communication 12. Synthesis of 3′(2′)-O-L-aminoacylnucleotides without prior protection of the amino group

1. A new one-step method was developed for the synthesis of 3′(2′)-O-aminoacylnucleotides by the reaction of protonated amino acids with nucleoside 5′-phosphates in the presence of N,N-carbonyldiimidazole. 2. It was shown that racemization is absent during the formation of the imidazolides of N-protonated amino acids and the condensation of the latter with nucleotides in aqueous medium.

Synthesis of aminoacyl derivatives of nucleosides, nucleotides, and polynucleotides

The possibility has been shown of extending the method of synthesis of O-aminoacyl derivatives of nucleotides and nucleoside triphosphates to prepare 3′(2′)-O-peptidyI-micleoside-5′-triphosphates.