A new chemical synthesis of 2-amino-(N-D-ribofuranosyl)acetamide 5'-phosphate.
2-Amino-(N-D-ribosyl)acetamide 5'-phosphate (GAR,10) has been prepared in a readily scaled-up synthesis from 2,3-O-isopropylidene-D-ribofuranosylamine p-toluenesulfonate (3) by condensation with the mixed anhydride of N-)benzyloxy-carbonyl)glycine, followed by phosphorylation with 2-cyanoethyl phosphate and removal of the protecting groups. By varying the conditions, the alpha-4 and the beta-5 anomers could be obtained and separated from each other. Anomerization occurs upon removing the O-isopropylidene group from either 7 or 8, so that the final compound (10) is an equimolar mixture of both anomers, of which only one is active toward GAR-transformylase.
D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008722:Methods; D012265:Ribonucleotides / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014166:Transferases / Q000378:metabolism
D012265:Ribonucleotides; D014166:Transferases