7273-34-9Relevant academic research and scientific papers
Syntheses and evaluation of the bioluminescent activity of (S)-Cypridina luciferin and its analogs
Wu, Chun,Kawasaki, Kosei,Ohgiya, Satoru,Ohmiya, Yoshihiro
, p. 753 - 756 (2007/10/03)
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 α-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.
Convergent and short-step syntheses of dl-Cypridina luciferin and its analogues based on Pd-mediated cross couplings
Nakamura, Hideshi,Aizawa, Mihoko,Takeuchi, Daisuke,Murai, Akio,Shimoura, Osamu
, p. 2185 - 2188 (2007/10/03)
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. (C) 2000 Elsevier Science Ltd.
STRUCTURE OF CYPRIDINA BILUCIFERYL, A DIMER OF CYPRIDINA LUCIFERYL RADICAL HAVING BIOLUMINESCENT ACTIVITY
Toya, Yoshiaki,Nakatsuka, Shin-ichi,Goto, Toshio
, p. 239 - 242 (2007/10/02)
Structure of Cypridina biluciferyl (luciferyl radical dimer), which is produced by chemical oxidation of C. luciferin with such as ferricyanide, was determined to be the symmetric 5,5'-dimer of C. luciferin.It gives light in the presence of C. luciferase, although the bioluminescent rate is very low.We suggest that the biluciferyl is an intermediate in the oxidation of the luciferin to C. luciferinol.
STRUCTURE OF CYPRIDINA LUCIFERINOL, "REVERSIBLY OXIDIZED CYPRIDINA LUCIFERIN"
Toya, Yoshiaki,Nakatsuka, Shin-ichi,Goto, Toshio
, p. 5753 - 5756 (2007/10/02)
Structure of Cypridina luciferinol (reversibly oxidized luciferin), which is produced by autooxidation or PbO2 oxidation of Cypridina luciferin without light production and can be reduced to C. luciferin with Na2S2O4 or NaBH4, was determined to be 2.
