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Synthesis 2014; 46(05): 646-652
DOI: 10.1055/s-0033-1340556
DOI: 10.1055/s-0033-1340556
paper
Strategies for Large-Scale Synthesis of Coelenterazine for in Vivo Applications
Further Information
Publication History
Received: 25 November 2013
Accepted after revision: 10 December 2013
Publication Date:
09 January 2014 (online)
Abstract
A new application of two Negishi-type coupling reactions for the synthesis of coelenterazine is reported. The synthesis of coelenterazine in high purity on a gram scale will enable numerous approaches to bioluminescence imaging and possibly photodynamic therapy of deep-seated tumors. Coelenterazine is the substrate for several luciferases, among them Gaussia luciferase (gLuc). This synthesis starts with pyrazin-2-amine and uses inexpensive starting materials and catalysts.
Key words
palladium - zinc - organometallic reagents - Grignard reaction - regioselectivity - Negishi couplingSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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