In conclusion, non-hydrolyzable substrate analogs for Asp- amidotransferase (GatCAB) were synthesized with overall yields from 2% to 14%. The synthetic route reported of the amino protection/deprotection herein does not require periodinane was group on the adenine moiety, and Dess-Martin proven to be a suitable oxidant for the conversion of both the 2' and 3'-hydroxyl groups of the ribose into the keto-adenosine inter mediates, and applicable for large scale synthesis. The DFT calcula tions suggest the origin of the formation of the 2-ketone hydrate via the internal hydrogen bond network, which was not observed between in the 3'-keto isomer. Investigations on the interactions substrate analogs the GatCAB enzyme and these non-hydrolyzable are in progress.