2] Synthesis of aminoacyl-N10 adenines

Abstract

This chapter describes the principle of synthesis of aminoacyl-N 10 adenines. The aminoacyl-N 10 adenines are prepared by condensing carbobenzoxyamino acids (Z-amino acids) and adenine with N,N'-dicyclohexylcarbodiimide (DCC) in dimethyl sulfoxide and decarbobenzoxylating the product with HBr. The ultraviolet absorption spectrum of L-isoleucyladenine with an absorption maximum at 282 mμ is characteristic of the aminoacyl-N 10 adenines. In synthesis of Z -aminoacyl-N 10 Adenines (II) the N-carbobenzoxy derivatives of glycine, L-alanine, DL-valine, L-leucine, L-isoleucine, and L-phenylalanine, are prepared essentially by the method of Bergmann and Zervas. Adenine (I), the Z-amino acid, and DCC in equimolar proportions were dissolved in hot (90°) dimethyl sulfoxide (0.4 M adenine) and allowed to cool and then stand at room temperature for 48 hours. Large needles of dicyclohexylurea are formed and removed by filtration. In aminoacyl-N 10 adenines (III) treatment of the Z-aminoacyl-N 10 adenines with a 34% solution of anhydrous HBr in glacial acetic acid resulted in removal of the carbobenzoxy groups.