Porphyrin substituted phosphoramidites: new building blocks for porphyrin-oligonucleotide syntheses
Porphyrin substituted phosphoramidites: new building blocks for porphyrin-oligonucleotide syntheses
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DOI：
10.1016/j.bmc.2005.01.045
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发表时间：
2005-04-01
影响因子：
3.5
通讯作者：
Berova, N
中科院分区：
文献类型：
--
作者：
Balaz, M;Holmes, AE;Berova, N
合成了含有三吡啶基苯基和四苯基卟啉发色团的胸苷亚磷酰胺，并将其用作自互补8聚体寡核苷酸3 '-T-5'-GCGCGCA-3'和5'-ACGCGCGT-3 '的固相合成中的结构单元。据我们所知，这些是第一个在3 '-位携带卟啉发色团的卟啉-寡核苷酸缀合物。通过自动化固相合成和通过市售的固体支持的寡核苷酸的廉价的直接“在烧瓶中”修饰实现链组装。这种方法允许合成修饰的寡核苷酸，而不使用昂贵的自动化DNA合成仪器。含卟啉的自互补寡核苷酸有望成为一种有价值的模型，用于药物结合研究和使用圆二色性测定DNA序列中的构象变化。(c)2005爱思唯尔有限公司保留所有权利。
Thymidine phosphoramidites containing trispyridylphenyl and tetraphenylporphyrin chromophores attached via a short amide linker in the 3'-position have been synthesized and used as building blocks in solid-phase synthesis of self-complementary 8-mer oligonucleotides 3'-T-5'-GCGCGCA-3' and 5'-ACGCGCGT-3'. To our knowledge, these are the first porphyrin-oligonucleotide conjugates carrying the porphyrin chromophores in the 3'-position. Chain assembly was achieved by automated solid-phase synthesis and by inexpensive straightforward `in flask' modification of commercially available solid supported oligonucleotides. This approach allows the synthesis of modified oligonucleotides without using costly instrumentation for automated DNA synthesis. Porphyrin-containing self-complementary oligonucleotides are expected to be a valuable model for drug binding studies and determination of conformational changes in DNA sequences using circular dichroism. (c) 2005 Elsevier Ltd. All rights reserved.