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Organic Letters: WuXi AppTec Developed Novel Photoredox-Mediated Decarboxylative Coupling between α Amino Acids and DNA-Conjugated Carbonyls

Organic Letters: WuXi AppTec Developed Novel Photoredox-Mediated Decarboxylative Coupling between α‑Amino Acids and DNA-Conjugated Carbonyls

 

2020/12/21 

 

DNA-encoded library (DEL) technology is a powerful and valuable tool commonly used by the pharmaceutical industry for the identification of compounds with affinity to biomolecular targets. Success in this endeavor lies in sampling diverse chemical libraries. However, current DNA-encoded library technology tend to be deficient in C(sp3) carbon counts.

 

Recently, WuXi AppTec HitS Unit has reported a DNA-compatible photoredox decarboxylative coupling reaction between α-amino acids and carbonyl compounds for the efficient synthesis of DNA-conjugated sp3-rich 1,2-amino alcohols. The reaction proceeds efficiently for a wide range of DNA-conjugated aldehydes and ketones under mild conditions, and provides the desired 1,2-amino alcohols with high conversions, enjoys huge potential and broad prospect in the DNA-encoded library production. Also, qPCR and sequencing data analysis indicates no significant DNA damage upon photoredox decarboxylative coupling reaction.

 

This work has been published on Organic Letters as the cover article.

Scheme. Photoredox decarboxylative coupling of α-amino acids with carbonyl compounds

 

Reference:

 

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