Novel Chemoenzymatic Protocol for the Synthesis of 3'-O-Dimethoxytrityl-2'-deoxynucleoside Derivatives as Building Blocks for Oligonucleotide Synthesis

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• 作者：Alba D&iacute ; az-Rodr&iacute ; guez ; Susana Ferná ; ndez ; Yogesh S. Sanghvi ; Miguel Ferrero ; and Vicente Gotor
• 刊名：Organic Process Research & Development
• 出版年：2006
• 出版时间：May 2006
• 年：2006
• 卷：10
• 期：3
• 页码：581 - 587
• 全文大小：100K
• 年卷期：v.10,no.3(May 2006)
• ISSN：1520-586X

文摘

An easy, efficient, and scalable chemoenzymatic strategy forthe synthesis of 3'-O-dimethoxytrityl-2'-deoxynucleosides hasbeen developed. A key feature of this approach is the regioselective synthesis of 5'-O-levulinyl-2'-deoxynucleosides throughenzymatic acylation in the presence of Candida antarctica lipaseB. In addition, it was observed that the deblocking of levulinylgroup from the 5'-position is perfectly compatible with conventional base protecting groups. To demonstrate the scalabilityof this method, 3'-O-dimethoxytritylthymidine (4a) was synthesized on 25-g scale. These monomers (4a-d) are usefulbuilding blocks for the synthesis of oligonucleotides.