Installing amino acids and peptides on N-heterocycles under visible-light assistance

Scientific Reports
Yunhe JinHua Fu

Abstract

Readily available natural α-amino acids are one of nature's most attractive and versatile building blocks in synthesis of natural products and biomolecules. Peptides and N-heterocycles exhibit various biological and pharmaceutical functions. Conjugation of amino acids or peptides with N-heterocycles provides boundless potentiality for screening and discovery of diverse biologically active molecules. However, it is a great challenge to install amino acids or peptides on N-heterocycles through formation of carbon-carbon bonds under mild conditions. In this article, eighteen N-protected α-amino acids and three peptides were well assembled on phenanthridine derivatives via couplings of N-protected α-amino acid and peptide active esters with substituted 2-isocyanobiphenyls at room temperature under visible-light assistance. Furthermore, N-Boc-proline residue was successfully conjugated with oxindole derivatives using similar procedures. The simple protocol, mild reaction conditions, fast reaction, and high efficiency of this method make it an important strategy for synthesis of diverse molecules containing amino acid and peptide fragments.

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Citations

Jan 13, 2017·Chemistry : a European Journal·Wan-Min ChengYao Fu
Nov 20, 2016·Chemistry : a European Journal·Tuhin Patra, Debabrata Maiti
Dec 19, 2019·Chemical Communications : Chem Comm·José Tiago M CorreiaMárcio Weber Paixão
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Oct 30, 2020·Chemical Communications : Chem Comm·Bei-Bei ZhanBing-Feng Shi
Nov 5, 2020·Angewandte Chemie·Liubov I PanferovaAlexander D Dilman
Dec 20, 2020·Biomolecules·Hunain AliFarzana Shaheen
Jul 2, 2021·Chemical Science·Wen WeiLutz Ackermann
Sep 25, 2017·Journal of the American Chemical Society·Yunhe JinHua Fu
Feb 19, 2020·The Journal of Organic Chemistry·Yan-Jun ZhuangYan-Biao Kang
Jun 28, 2017·Biochemistry·Justine N deGruyterPhil S Baran
Sep 3, 2021·Chemical Communications : Chem Comm·Xianjin Zhu, Hua Fu

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