Synthesis and selected properties of oligonucleotidyl-(Pm----O)-amino acids.
N-Cbz-Ser(OMe)-(Pm----O)-d(TpT) was synthesized as a diastereomeric mixture of approx. (1:1) by reacting d(TpT) with 2,4,6-triisopropylbenzenesulfonyl chloride and N-Cbz-Ser-OMe. The phosphoesteric bond of N-Cbz-Ser (OMe)-(Pm----O)-d(TpT) was found to be stable in acid (1 N HCl, 1 h, 37 degrees C), but labile in alkaline solution (0.1-1 N NaOH, 1 h, 37 degrees C). The products of alkaline hydrolysis were determined to be d(TpT) and the amino acid derivatives. Furthermore, the phosphotriester N-Cbz-Ser(OMe)-(Pm----O)-d(TpT) was more labile than the diesteric analogue N-Cbz-Ser (OMe)-pdT. The internucleotide phosphotriester linkage of N-Cbz-Ser (OMe)-(Pm----O)-d(TpT) was also found to be resistant to enzymatic digestion with spleen and snake venom phosphodiesterases.
Bagdoniene
L
L
Department of Biochemistry and Biophysics, Vilnius University, Lithuania SSR, USSR.
Plaipa
R
R
Juodka
B
B
D000596:Amino Acids; D006868:Hydrolysis; D008956:Models, Chemical; D009698:Nucleoproteins / Q000138:chemical synthesis*; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis*; D010727:Phosphoric Diester Hydrolases
D000596:Amino Acids; D009698:Nucleoproteins; D009838:Oligodeoxyribonucleotides; D010727:Phosphoric Diester Hydrolases