Strategies for Large-Scale Synthesis of Coelenterazine for in Vivo Applications

Tej B. Shrestha; Deryl L. Troyer; Stefan H. Bossmann

doi:10.1055/s-0033-1340556

Synthesis, Inhaltsverzeichnis

Synthesis 2014; 46(05): 646-652
DOI: 10.1055/s-0033-1340556

paper

Strategies for Large-Scale Synthesis of Coelenterazine for in Vivo Applications

Tej B. Shrestha*

^aKansas State University, Department of Chemistry, 213 CBC Building, Manhattan, KS 66506, USA Fax: +1(785)5326666 eMail: sbossman@ksu.edu

^bKansas State University, Anatomy & Physiology, 130 Coles Hall, Manhattan, KS, 66506, USA eMail: tbs3@vet.k-state.edu

,

Deryl L. Troyer

^bKansas State University, Anatomy & Physiology, 130 Coles Hall, Manhattan, KS, 66506, USA eMail: tbs3@vet.k-state.edu

,

Stefan H. Bossmann*

^aKansas State University, Department of Chemistry, 213 CBC Building, Manhattan, KS 66506, USA Fax: +1(785)5326666 eMail: sbossman@ksu.edu

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Abstract

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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 coupling

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Referenzen

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