Cargando…
Installing amino acids and peptides on N-heterocycles under visible-light assistance
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...
Autores principales: | , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Nature Publishing Group
2016
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4735789/ https://www.ncbi.nlm.nih.gov/pubmed/26830014 http://dx.doi.org/10.1038/srep20068 |
_version_ | 1782413145287950336 |
---|---|
author | Jin, Yunhe Jiang, Min Wang, Hui Fu, Hua |
author_facet | Jin, Yunhe Jiang, Min Wang, Hui Fu, Hua |
author_sort | Jin, Yunhe |
collection | PubMed |
description | 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. |
format | Online Article Text |
id | pubmed-4735789 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | Nature Publishing Group |
record_format | MEDLINE/PubMed |
spelling | pubmed-47357892016-02-05 Installing amino acids and peptides on N-heterocycles under visible-light assistance Jin, Yunhe Jiang, Min Wang, Hui Fu, Hua Sci Rep Article 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. Nature Publishing Group 2016-02-02 /pmc/articles/PMC4735789/ /pubmed/26830014 http://dx.doi.org/10.1038/srep20068 Text en Copyright © 2016, Macmillan Publishers Limited http://creativecommons.org/licenses/by/4.0/ This work is licensed under a Creative Commons Attribution 4.0 International License. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in the credit line; if the material is not included under the Creative Commons license, users will need to obtain permission from the license holder to reproduce the material. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/ |
spellingShingle | Article Jin, Yunhe Jiang, Min Wang, Hui Fu, Hua Installing amino acids and peptides on N-heterocycles under visible-light assistance |
title | Installing amino acids and peptides on N-heterocycles under visible-light assistance |
title_full | Installing amino acids and peptides on N-heterocycles under visible-light assistance |
title_fullStr | Installing amino acids and peptides on N-heterocycles under visible-light assistance |
title_full_unstemmed | Installing amino acids and peptides on N-heterocycles under visible-light assistance |
title_short | Installing amino acids and peptides on N-heterocycles under visible-light assistance |
title_sort | installing amino acids and peptides on n-heterocycles under visible-light assistance |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4735789/ https://www.ncbi.nlm.nih.gov/pubmed/26830014 http://dx.doi.org/10.1038/srep20068 |
work_keys_str_mv | AT jinyunhe installingaminoacidsandpeptidesonnheterocyclesundervisiblelightassistance AT jiangmin installingaminoacidsandpeptidesonnheterocyclesundervisiblelightassistance AT wanghui installingaminoacidsandpeptidesonnheterocyclesundervisiblelightassistance AT fuhua installingaminoacidsandpeptidesonnheterocyclesundervisiblelightassistance |