Matsuno Yuki, Shoji Takao, Kim Shokaku, Chiba Kazuhiro
Laboratory of Bio-organic Chemistry, Tokyo University of Agriculture and Technology , 3-5-8 Saiwai-cho, Fuchu, Tokyo 183-8509, Japan.
Org Lett. 2016 Feb 19;18(4):800-3. doi: 10.1021/acs.orglett.6b00077. Epub 2016 Feb 4.
A straightforward method for the synthesis of oligonucleotide blocks using a Cbz-type alkyl-chain-soluble support (Z-ACSS) attached to the 3'-OH group of 3'-terminal nucleosides was developed. The Z-ACSS allowed for the preparation of fully protected deoxyribo- and ribo-oligonucleotides without chromatographic purification and released dimer- to tetramer-size oligonucleotide blocks via hydrogenation using a Pd/C catalyst without significant loss or migration of protective groups such as 5'-end 4,4'-dimethoxtrityl, 2-cyanoethyl on internucleotide bonds, or 2'-TBS.
开发了一种直接的方法，用于使用连接到3'-末端核苷3'-OH基团的Cbz型烷基链可溶性支持物（Z-ACSS）合成寡核苷酸片段。Z-ACSS允许制备无需色谱纯化的完全保护的脱氧核糖和核糖寡核苷酸，并通过使用Pd/C催化剂进行氢化反应释放二聚体至四聚体大小的寡核苷酸片段，而不会导致5'-末端4,4'-二甲氧基三苯甲基、核苷酸间键上的2-氰基乙基或2'-TBS等保护基团发生明显损失或迁移。
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