Huanan Wen; Rui Ge; Yi Qu; Jialin Sun; Xiaodong Shi; Weiren Cui; Hao Yan; Qi Zhang; Yulong An; Wenji Su; Hongfang Yang; Letian Kuai; Alexander L. Satz; Xuanjia Peng
Org. Lett., 2020, 22(24), 9484-9489
https://doi.org/10.1021/acs.orglett.0c03461

Abstract

We report a DNA-compatible photoredox decarboxylative coupling of α-amino acids with carbonyl compounds to access DNA-encoded sp3-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.