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Urease: A highly biocompatible catalyst for switchable Biginelli reaction and synthesis of 1,4-dihydropyridines from the in situ formed ammonia

Paper ID Volume ID Publish Year Pages File Format Full-Text
49632 46757 2015 5 PDF Available
Title
Urease: A highly biocompatible catalyst for switchable Biginelli reaction and synthesis of 1,4-dihydropyridines from the in situ formed ammonia
Abstract

•Urea is a natural odorless source of nitrogen for synthesis of 1,4-dihydropyridines.•Water-based reaction with urea and urease is highly biocompatible.•Reactions give excellent yields of products without purification.•Urease catalyzes Hantzsch reaction with urea in water more than NH4OAc.•This enzymatic medium is reusable and inhibits by heavy metal cations.

Urease is a superior biocompatible catalyst for switching from the Biginelli reaction to urea-based synthesis of 1,4-dihydropyridines in water, where 100% switching occurs at 0.02 g/mL of enzyme. Hantzsch reaction with ammonium acetate (NH4OAc) is inefficiently catalyzed by urease (70%, 4 h), and heavy metal ions inhibit the urease-catalyzed reactions with urea or NH4OAc. Promotion of the urea-based Hantzsch reaction by urease and its inhibition with Hg2 + supports specificity of urease for in situ generation of ammonia, whereas the role of urease in further transformations is not so specific. The features of this enzymatic method are reusability, mild reaction conditions, biocompatibility, generality, and high yield of products.

Graphical abstractUrease is a biocatalyst for switching of the Biginelli reaction to urea-based Hantzsch synthesis of 1,4-dihydropyridines in water, while urease-catalyzed Hantzsch reaction with either urea or ammonium salt inhibits by trace amounts of Hg2 + and Ag+.Figure optionsDownload full-size imageDownload as PowerPoint slide

Keywords
Urease; Water-based Hantzsch reaction; Enzymatic; Biocompatible
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Urease: A highly biocompatible catalyst for switchable Biginelli reaction and synthesis of 1,4-dihydropyridines from the in situ formed ammonia
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Publisher
Database: Elsevier - ScienceDirect
Journal: Catalysis Communications - Volume 72, 5 December 2015, Pages 63–67
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
Get Full-Text Now
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Price was $35.95
You save - $31
Price after discount Only $4.95
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Online Support
Any Questions? feel free to contact us