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Li Z, Yu B. HFIP-Promoted de Novo Synthesis of Biologically Relevant Nonnatural α-Arylated Amino Esters and Dipeptide Mimetics. Chemistry. 2019;doi: 10.1002/chem.201904395.
Li, Z., & Yu, B. (2019). HFIP-Promoted de Novo Synthesis of Biologically Relevant Nonnatural α-Arylated Amino Esters and Dipeptide Mimetics. Chemistry (Weinheim an der Bergstrasse, Germany), . https://doi.org/10.1002/chem.201904395
Li, Zhonghua, and Yu, Bin. "HFIP-Promoted de Novo Synthesis of Biologically Relevant Nonnatural α-Arylated Amino Esters and Dipeptide Mimetics." Chemistry (Weinheim an der Bergstrasse, Germany) vol. (2019). doi: https://doi.org/10.1002/chem.201904395
Li Z, Yu B. HFIP-Promoted de Novo Synthesis of Biologically Relevant Nonnatural α-Arylated Amino Esters and Dipeptide Mimetics. Chemistry. 2019 Oct 16; doi: 10.1002/chem.201904395. Epub 2019 Oct 16. PMID: 31617627.
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Chemistry. 2019 Oct 16; doi: 10.1002/chem.201904395. Epub 2019 Oct 16.

HFIP-Promoted de Novo Synthesis of Biologically Relevant Nonnatural α-Arylated Amino Esters and Dipeptide Mimetics.

Chemistry (Weinheim an der Bergstrasse, Germany)

Zhonghua Li, Bin Yu

Affiliations

  1. Scientific Research Center & Laboratory Animal Center, Henan University of Chinese Medicine, 156 Jinshui East Road, 450046, Zhengzhou, Henan, P. R. China.
  2. School of Pharmaceutical Sciences, Zhengzhou University, 100 Science Avenue, 450001, Zhengzhou, Henan, P. R. China.
  3. State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, 210023, P. R. China.

PMID: 31617627 DOI: 10.1002/chem.201904395

Abstract

Amino acids are fundamental building blocks, which have been extensively used in drug design and organic synthesis. However, nonnatural amino acids are relatively less studied. In this work, the authors report the first HFIP-promoted de novo synthesis of nonnatural α-arylated amino esters and dipeptide mimetics (27 examples, up to 99 % yield) from readily available amines, ethyl glyoxylate and electron-rich arenes under mild conditions, in which one C-C bond, one C-N bond and one chiral center were established simultaneously. The reaction was also performed on a gram scale, giving compound 4 a in 96 % yield. In addition, this protocol was successfully applied to the late-stage elaboration of drug molecules, such as tranylcypromine (TCP or PCPA) and troxipide. Interestingly, compound 4 h inactivated histone lysine specific demethylase 1 (LSD1) potently with an IC

© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: HFIP; LSD1 inhibitors; cascade reactions; histone demethylase; nonnatural amino acids

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