WuXi AppTec (Shanghai) Co., Ltd., 288 Fute Zhong Road, Waigaoqiao Free Trade Zone, Shanghai 200131, China.
Org Lett. 2020 Dec 18;22(24):9484-9489. doi: 10.1021/acs.orglett.0c03461. Epub 2020 Nov 10.
We report a DNA-compatible photoredox decarboxylative coupling of α-amino acids with carbonyl compounds to access DNA-encoded sp-rich 1,2-amino alcohols. The reaction proceeds efficiently for a wide range of DNA-conjugated aldehydes and ketones and provides the desired 1,2-amino alcohols with conversions generally >50%. Additional utility of the developed protocol is demonstrated by one-pot cyclization of DNA-conjugated 1,2-amino alcohols into oxazolidiones and morpholinones. Lastly, qPCR and sequencing data analysis indicates no significant DNA damage upon photoredox decarboxylative coupling.
我们报告了一种 DNA 兼容的光氧化还原脱羧偶联反应，可将α-氨基酸与羰基化合物偶联，从而获得 DNA 编码的富含 sp 的 1,2-氨基醇。该反应对广泛的 DNA 连接的醛和酮都能高效进行，通常转化率>50%，即可得到所需的 1,2-氨基醇。通过 DNA 连接的 1,2-氨基醇一锅法环化，进一步证明了所开发的反应方案的实用性，可得到噁唑烷酮和吗啉酮。最后，qPCR 和测序数据分析表明，光氧化还原脱羧偶联反应不会导致 DNA 明显损伤。
