3055-23-0Relevant articles and documents
A Chemoenzymatic Route to Prepare Acyclic Nucleoside Analogues
Palazzolo, Martín A.,Nigro, Mariano J.,Iribarren, Adolfo M.,Lewkowicz, Elizabeth Sandra
, p. 921 - 924 (2016)
Acyclic nucleosides are potential antiviral and antitumor agents. In this work, their preparation through a novel chemoenzymatic procedure involving the N-alkylation of a nucleobase and subsequent aldol condensation catalyzed by a dihydroxyacetone phosphate-dependant aldolase (Rabbit Muscle Aldolase, RAMA) is described.
A short de novo synthesis of nucleoside analogs
Adluri, Bharanishashank,Britton, Robert,Campeau, Louis-Charles,Cohen, Ryan,Lehmann, Johannes,Meanwell, Michael,Silverman, Steven M.,Wang, Yang
, p. 725 - 730 (2020/09/02)
Nucleoside analogs are commonly used in the treatment of cancer and viral infections. Their syntheses benefit from decades of research but are often protracted, unamenable to diversification, and reliant on a limited pool of chiral carbohydrate starting materials. We present a process for rapidly constructing nucleoside analogs from simple achiral materials. Using only proline catalysis, heteroaryl-substituted acetaldehydes are fluorinated and then directly engaged in enantioselective aldol reactions in a one-pot reaction. A subsequent intramolecular fluoride displacement reaction provides a functionalized nucleoside analog. The versatility of this process is highlighted in multigram syntheses of D- or L-nucleoside analogs, locked nucleic acids, iminonucleosides, and C2′- and C4′-modified nucleoside analogs. This de novo synthesis creates opportunities for the preparation of diversity libraries and will support efforts in both drug discovery and development.
Synthesis of novel mimetics of CMP-sialic acid as the inhibitors of sialyltransferases
Tanaka, Toru,Ozawa, Machiko,Miura, Tsuyoshi,Inazu, Toshiyuki,Tsuji, Shuichi,Kajimoto, Tetsuya
, p. 1487 - 1490 (2007/10/03)
Novel mimetics of CMP-sialic acid were designed as the inhibitors of sialyltransferases. They were synthesized in a short step from a cytosine carrying β-hydroxy-α-L-amino acid based on the knowledge that nikkomycin, a peptidic derivative of an uracil carrying amino acid, shows a potent inhibitory activity toward N-acetyl-D-glucosaminyltransferases that employ UDP-N-acetyl-D-glucosamine as the donor substrate. The cytosine carrying β-hydroxyl-α-L-amino acid, a key intermediate in our synthetic strategy, was easily prepared by the L-threonine aldolase (LTA) catalyzed reaction.