Acetylated and Methylated beta-Cyclodextrins as Viable Soluble Supports for the Synthesis of Short 2 %26apos;-Oligodeoxyribo-nucleotides in Solution

作者：Molina Alejandro Gimenez; Kungurtsev Vyacheslav; Virta Pasi; Lonnberg Harri^*

来源：Molecules, 2012, 17(10): 12102-12120.

DOI：10.3390/molecules171012102

• cyclodextrin
• oligonucleotides
• phosphoramidites
• soluble support
• synthesis

Novel soluble supports for oligonucleotide synthesis 11a-c have been prepared by immobilizing a 5%26apos;-O-protected 3%26apos;-O-(hex-5-ynoyl) thymidine (6 or 7) to peracetylated or permethylated 6-deoxy-6-azido-beta-cyclodextrins 10a or 10b by Cu(I)-promoted 1,3-dipolar cycloaddition. The applicability of the supports to oligonucleotide synthesis by the phosphoramidite strategy has been demonstrated by assembling a 3%26apos;-TTT-5%26apos; trimer from commercially available 5%26apos;-O-(4,4%26apos;-dimethoxytrityl) thymidine 3%26apos;-phosphoramidite. To simplify the coupling cycle, the 5%26apos;-O-(4,4%26apos;-dimethoxytrityl) protecting group has been replaced with an acetal that upon acidolytic removal yields volatile products. For this purpose, 5%26apos;-O-(1-methoxy-1-methylethyl)-protected 3%26apos;-(2-cyanoethyl-N, N-diisopropyl-phosphoramidite) s of thymidine (5a), N-4-benzoyl-2%26apos;-deoxycytidine (5b) and N-6-benzoyl-2%26apos;-deoxyadenosine (5c) have been synthesized and utilized in synthesis of a pentameric oligonucleotide 3%26apos;-TTCAT-5%26apos; on the permethylated cyclodextrin support 11c.

• 出版日期2012-10