[摘要]：The synthesis and biophysical evaluation of 3'-Me-alpha-L-LNA is reported. The synthesis of the nucleoside building block phosphoramidite was accomplished starting from diacetone glucose. The 3'-Me group was introduced in the desired configuration by hydride mediated opening of an exocyclic epoxide. Inversion of the 2'-hydroxyl group was achieved by means of an oxidation/reduction sequence followed by cyclization onto a 5'-leaving group to assemble the [2.2.1] ring system. Biophysical evaluation of 3'-Me-alpha-L-LNA modified oligonucleotides showed good duplex thermal stabilizing properties which were similar to alpha-L-LNA. Mismatch discrimination experiments revealed that 3'-Me-alpha-L-LNA possess slightly enhanced discrimination properties for the GU wobble base-pair as compared to related nucleic acid analogs. (C) 2011 Elsevier Ltd. All rights reserved.
