Solid-Phase Synthesis of Pyrrole Derivatives through a Multicomponent Reaction Involving Lys-Containing Peptides

Yahya E Jad; Santosh K Gudimella; Thavendran Govender; Beatriz G de la Torre; Fernando Albericio

doi:10.1021/acscombsci.8b00006

Solid-Phase Synthesis of Pyrrole Derivatives through a Multicomponent Reaction Involving Lys-Containing Peptides

ACS Comb Sci. 2018 Apr 9;20(4):187-191. doi: 10.1021/acscombsci.8b00006. Epub 2018 Feb 22.

Authors

Yahya E Jad¹, Santosh K Gudimella^{1

2}, Thavendran Govender¹, Beatriz G de la Torre^{1

3}, Fernando Albericio^{1

2

4

5}

Affiliations

¹ Catalysis and Peptide Research Unit , School of Health Sciences, University of KwaZulu-Natal , University Road , Westville, Durban 4001 , South Africa.
² School of Chemistry and Physics , University of KwaZulu-Natal , University Road , Westville, Durban 4001 , South Africa.
³ KRISP, College of Health Sciences , University of KwaZulu-Natal , Durban 4001 , South Africa.
⁴ Department of Organic Chemistry , University of Barcelona , 08028 Barcelona , Spain.
⁵ CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine , Barcelona Science Park , 08028 Barcelona , Spain.

PMID: 29444402
DOI: 10.1021/acscombsci.8b00006

Abstract

The synthesis of pyrroles has received considerable attention because of their biological and pharmaceutical activities. Herein we describe a solid-phase multicomponent reaction that utilizes Lys as a N donor, β-nitrostyrenes, 1,3-dicarbonyl compounds, and FeCl₃ as an easily accessible catalyst under microwave irradiation to afford the subsequent pyrrole derivatives in high conversions. The strategy combines three of the most powerful tools in modern synthetic chemistry: the solid-phase mode, microwave activation, and a multicomponent reaction. The excellent results in terms of rapidity, versatility, and purity obtained herein support once again that this combined strategy is efficient for gaining chemical diversity.

Keywords: combinatorial libraries; multicomponent reaction; pyrrole; solid-phase peptide synthesis.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Combinatorial Chemistry Techniques
Iron Compounds / chemistry
Lysine / analogs & derivatives*
Lysine / chemistry*
Microwaves
Molecular Structure
Nitrogen / chemistry
Peptides / chemical synthesis*
Pyrroles / chemical synthesis*
Small Molecule Libraries
Solid-Phase Synthesis Techniques
Styrenes / chemistry

Substances

Iron Compounds
Peptides
Pyrroles
Small Molecule Libraries
Styrenes
Lysine
Nitrogen