Convergent and short-step syntheses of dl-Cypridina luciferin and its analogues based on Pd-mediated cross couplings
Tetrahedron Letters(2000)
Abstract
dl-Cypridina luciferin and its analogues were synthesized from 2-aminopyrazine by an eight-step method that included two regio-selective Pd-mediated cross couplings, and their chemi- and bioluminescent activities were compared. Analogues having a 3-benzofuranyl or a 3-benzothienyl group in the place of a 3-indolyl group showed luciferase affinities similar to Cypridina luciferase but with a lower luminescent efficiency, suggesting that the NH group is unimportant for molecular recognition whereas the indolyl group is crucial for efficient luminescence.
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Key words
benzofurans,bioluminescence,benzothiophenes,indoles
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