Synthesis of Nucleotide α-Amino Acids via New Branched Chain Sugar

Abstract

Muqdad Irhaeem Kadhim, Abeer Hamoodi Jabbar

This work includes synthesis of new N-substituted nucleotide α-amino acids, in order to obtain these derivatives; 3-keto sugar derivative was subjected to a modified strecker-type reaction, where by different primary aromatic amine with cyanide ion were introduced successfully, and new α-aminonitriles were thus obtained in good yields.
Base hydrolysis of sugar α-aminonitriles by using (35 %) aqueous sodium hydroxide solution, at reflux temperature gave the desired sugar α-amino acids. FTIR spectroscopy was utilized for characterization of synthesized compounds.
In order to synthesis the new nucleotides, the branched chains sugars modified to either active forms as acetyl sugar derivative or (1-bromosugar derivatives). When use 1-bromosugar the conversion include the hydrolysis to the corresponding diol, acetylation with acetic acid/acetic anhydride in acidic to furnished the acetylated sugar, bromination, forming 1-bromo, that was subjected to condensations with mercury base salts to gives aprtected nucleotides. DE blocking of these groups with (CH3ONa / CH3OH produced nucleotides free analogue type of (2',3')-dideoxye-(3',3')-amine carboxyl - pyrano).