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首页> 外文期刊>Current Protocols in Nucleic Acid Chemistry >Synthesis of 2'-Fluorinated Northern Methanocarbacyclic (2'-F-NMC) Nucleosides and Their Incorporation Into Oligonucleotides
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Synthesis of 2'-Fluorinated Northern Methanocarbacyclic (2'-F-NMC) Nucleosides and Their Incorporation Into Oligonucleotides

机译：合成2氟化的北部Methanocarbacyclic -F-NMC(2)核苷他们并入寡核苷酸

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摘要

This article describes chemical synthesis of 2'-fluorinated Northern methanocarbacyclic (2'-F-NMC) nucleosides and phosphoramidites, based on a bicyclo[3.1.0]hexane scaffold bearing all four natural nucleobases (U, C, A, and G), and their incorporation into oligonucleotides by solid-supported synthesis. This synthesis starts from commercially available cyclopent-2-en-1-one to obtain the fluorinated carbocyclic pseudosugar intermediate (S.13), which can be converted to the uridine intermediate by condensation with isocyanate, followed by cyclization, and to adenine and guanine precursors by microwave-assisted reactions. All four 2'-F-NMC phosphoramidites are synthesized from S.13 in a convergent approach, and the monomers are used for synthesis of 2'-F-NMC-modified oligonucleotides.
机译：本文介绍了化学合成的2》氟methanocarbacyclic北部(2 ' -F-NMC)核苷和phosphoramidites,基于bicyclo[3.1.0]己烷支架轴承所有四个自然碱基(U, C, A和G),和他们并入寡核苷酸solid-supported合成。从商用cyclopent-2-en-1-one获取氟化碳环pseudosugar中间(S.13),它可以转化为尿苷的中间通过凝结异氰酸酯,其次是环合,腺嘌呤和鸟嘌呤的前兆微波反应。从S.13 phosphoramidites合成收敛的方法,使用单体2 ' -F-NMC-modified的合成寡核苷酸。

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