Nucleoside N-acylation with active derivatives of amino acids
DOI:
https://doi.org/10.7124/bc.000449Abstract
Simple procedure for N-acylation ofadenosine guanosine and cytidine by active derivatives of amino acids is proposed. Procedure is based on transient silyt protection ofribose hydroxy groups and consists of 3 steps: (a) silytotion of nucleoside by trimethylchloro-silane, (b) reaction of amino group ofsilylated nucleoside with chloroanhydride or active ester of N-protected amino acid, (c) desilylation of intermediate. The yields of N-amino-acylated nucleosides were about 40–90 %.References
Krayevsky AA, Watanabe KA. Modified nucleosides as anti-AIDS drugs: current status and perspectives. M.: Bioinform, 1993. 212 p.
Aggarwal SK, Gogu SR, Rangan SR, Agrawal KC. Synthesis and biological evaluation of prodrugs of zidovudine. J Med Chem. 1990;33(5):1505-10.
Abraham TW, Wagner CR. A Phosphoramidite-based synthesis of phosphoramidate amino acid diesters of antiviral nucleosides. Nucleosides Nucleotides. 1994;13(9):1891–903.
Shabarova ZA, Bogdanov AA. Chemistry of nucleic acids and their components. M.: Khimia, 1978: 88 p.
Nietzky R, Braunschweig E. Ueber die Einwirkung von Alkalien auf Orthonitrophenylhydrazin. Berichte der deutschen chemischen Gesellschaft. 1894; 27(3):3381—3384.
Greenstein JP, Winitz M. Chemistry of amino acids. New York; London, 1961: 465-7.
Ti GS, Gaffney BL, Jones RA. Transient protection: efficient one-flask syntheses of protected deoxynucleosides. J Am Chem Soc. 1982;104(5):1316–9.
Chaix C, Duplaa AM, Molko D, T?oule R. Solid phase synthesis of the 5'-half of the initiator t-RNA from B. subtilis. Nucleic Acids Res. 1989;17(18):7381-93.
Gait MJ, Matthes HWD, Singh M, Titmas RC Synthesis of oligodeoxyribonucleotides by a continuous flow phosphotriester method on a kieselguhr. polyamide support. Chemical and enzymatic synthesis of gene fragments: a laboratory manual. Eds. H. G. Gassen, A. Lang. Berlin: Verlag Chemie, 1982: 1-42.
