Journal
TETRAHEDRON LETTERS
Volume 47, Issue 5, Pages 753-756Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2005.11.119
Keywords
Cypridina luciferin; luciferase; bioluminescence; imidazopyrazinone
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Cypridina luciferin is the substrate in the bioluminescence of a luminous ostracod Cypridina (Vargula) hilgendorfii. Cypridina luciferin contains a chiral center in the sec-butyl moiety. Here, we report a convenient method for the preparation of (S)-Cypridina luciferin by the condensation of (S)-1,1-diethoxy-3-methylpentan-2-one with ethioluciferin. The light yield of the synthesized (S)-luciferin in the presence of Cypridina luciferase was about 1.7 times as active as that of racemic form. Furthermore, several luciferin analogs prepared by the same condensation with different alpha-ketoacetal derivatives showed moderate light yield with Cypridina luciferase. These readily available Cypridina luciferin and analogs are applicable to the bioluminescent detection of Cypridina luciferase. (c) 2005 Elsevier Ltd. All rights reserved.
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