Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.
Org Lett. 2011 Oct 21;13(20):5612-5. doi: 10.1021/ol202285y. Epub 2011 Sep 29.
A furan amino acid, inspired by the recently discovered proximicin natural products, was incorporated into the scaffold of a DNA-binding hairpin polyamide. While unpaired oligomers of 2,4-disubstituted furan amino acids show poor DNA-binding activity, furan (Fn) carboxamides paired with N-methylpyrrole (Py) and N-methylimidazole (Im) rings demonstrate excellent stabilization of duplex DNA as well as discrimination of noncognate sequences, consistent with function as a Py mimic according to the Py/Im polyamide pairing rules.
受近期发现的普罗米辛天然产物的启发，引入了一种呋喃氨基酸到 DNA 结合发夹状聚酰胺的结构中。虽然 2,4-二取代呋喃氨基酸的未配对寡聚物显示出较差的 DNA 结合活性，但与 N-甲基吡咯（Py）和 N-甲基咪唑（Im）环配对的呋喃（Fn）羧酰胺表现出对双链 DNA 的出色稳定作用，以及对非同源序列的区分能力，这与根据 Py/Im 聚酰胺配对规则作为 Py 类似物的功能一致。
