Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhopal Bypass Road, Bhauri, Bhopal 462066, MP, India.
Chem Commun (Camb). 2020 Nov 18;56(89):13832-13835. doi: 10.1039/d0cc05492e. Epub 2020 Oct 21.
Chemo- and site-specific modifications in oligonucleotides have wide applicability as mechanistic probes in chemical biology. However, methods that label specific sites in nucleic acids are scarce, especially for labeling DNA/RNA from biological or enzymatic sources rather than synthetic ones. Here we have employed a classical reaction, reductive amination, to selectively functionalize the N-amine of guanosine and 2'-deoxyguanosine monophosphate (GMP/dGMP). This method specifically modifies guanine in DNA and RNA oligonucleotides, while leaving the other nucleobases unaffected. Using this approach, we have successfully incorporated a reactive handle chemoselectively into nucleic acids for further functionalization and downstream applications.
在化学生物学中，寡核苷酸的化学和位置特异性修饰作为机制探针具有广泛的适用性。然而，标记核酸中特定位置的方法很少，特别是对于从生物或酶源而不是合成源标记 DNA/RNA。在这里，我们采用了一种经典反应——还原胺化反应，来选择性地对鸟嘌呤和 2'-脱氧鸟苷单磷酸（GMP/dGMP）的 N-胺进行功能化。该方法特异性修饰 DNA 和 RNA 寡核苷酸中的鸟嘌呤，而不影响其他碱基。使用这种方法，我们已经成功地将反应性接头选择性地掺入核酸中，用于进一步的功能化和下游应用。
