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Sugar?Oligoamides: Synthesis of DNA Minor Groove Binders

机译:糖寡酰胺:DNA小沟结合剂的合成

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摘要

Sugar-oligoamides have been designed andnsynthesized as structurally simple carbohydrate-based ligandsnto study carbohydrate−minor groove DNA interactions. Herenwe report an efficient solution-phase synthetic strategy tonobtain two broad families of sugar−oligoamides. The first type,nstructure vector A (-Py[Me]-γ-Py-Ind), has a methyl groupnpresent as a substituent on the nitrogen of pyrrole B, connectednto the C terminal of the oligoamide fragment. The second type,nstructure vector B (-Py[(CH2)11OH]-γ-Py-Ind), has an alkylnchain present on the nitrogen of pyrrole B connected to the Cnterminal of the oligoamide fragment and has been designed to access to di- and multivalent sugar−oligoamides. By usingnsequential DIPC/HOBt coupling reactions, the oligoamide fragment -Py[R]-γ-Py-Ind has been constructed. The last couplingnreaction between the anomeric amino sugar and the oligoamide fragment was carried out by activating the acid derivative as anBtO- ester, which has been performed by using TFFH. The isolated esters (BtO-Py[R]-γ-Py-Ind) were coupled with selectednamino sugars using DIEA in DMF. The synthesis of two different selective model vectors (vector A (1) and vector B (2)) andntwo types of water-soluble sugar−oligoamide ligands, with vector A structure (compounds 3−7) and with vector B structuren(compound 8), was carried out.
机译:糖-寡酰胺已被设计和合成为结构简单的基于碳水化合物的配体,从而研究了碳水化合物与小沟之间的DNA相互作用。 Herenwe报告了一种有效的溶液阶段合成策略,无法获得两个广泛的糖寡酰胺家族。第一种,n结构载体A(-Py [Me]-γ-Py-Ind),具有在吡咯B的氮上作为取代基存在的甲基,其连接至寡酰胺片段的C端。第二种,n结构向量B(-Py [((CH2)11OH]-γ-Py-Ind),在吡咯B的氮原子上存在与低酰胺片段的Cn末端连接的亚烷基链,并被设计为可与-和多价糖寡酰胺。通过使用顺序的DIPC / HOBt偶联反应,已构建了寡酰胺片段-Py [R]-γ-Py-Ind。端基氨基糖和寡酰胺片段之间的最后偶联反应是通过将酸衍生物活化为BtO-酯来进行的,这是通过使用TFFH进行的。使用DIEA在DMF中将分离的酯(BtO-Py [R]-γ-Py-Ind)与选定的氨基糖偶联。两种不同的选择性模型载体(载体A(1)和载体B(2))和两种类型的水溶性糖-寡酰胺配体的合成,具有载体A结构(化合物3-7)和载体B结构n(化合物8 ),已执行。

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  • 来源
    《The Journal of Organic Chemistry》 |2012年第23期|10870-10881|共12页
  • 作者单位

    Departamento de Sıń tesis Estructura y Propiedades de los Compuestos Orgań icos Instituto de Quıḿ ica Orgań ica General CSICnc/Juan de la Cierva 3 28006 Madrid Spain;

  • 收录信息 美国《科学引文索引》(SCI);美国《工程索引》(EI);美国《生物学医学文摘》(MEDLINE);美国《化学文摘》(CA);
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  • 正文语种 eng
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  • 入库时间 2022-08-17 13:29:34

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