Cypridina luciferin synthesis

Properties of luciferin. The crystals are microscopic needles, which melt with decomposition at 205-210°C (Bitler and McElroy, 1957). It is a quite stable luciferin compared with some other luciferins, such as Cypridina luciferin and the luciferins of krill and dinoflagellates. It is not significantly affected by lOmM H2SO4 and lOmM NaOH at room temperature in air. The absorption spectral data of luciferin are shown in Fig. 1.3 (McElroy and Seliger, 1961). The molar absorption coefficient of the 328 nm peak in acidic solutions and that of the 384 nm peak in basic solutions are both 18,200 (Morton et al., 1969). Luciferin is fluorescent, showing an emission maximum at 537 nm in both acidic and basic conditions, although the intensity of the fluorescence is lower in acidic solution than in basic solution (fluorescence quantum yields 0.62 in basic condition, and 0.25 in acidic condition Morton et al., 1969). The chemical synthesis... 

Thus, oxyluciferin has a molecular formula of C21H27ON72HCI. The total synthesis of Cypridina luciferin has been accomplished (Kishi et al., 1966c Inoue et al., 1969 Karpetsky and White, 1971 Nakamura et al., 2000). 

Inoue, S., Sugiura, S., Kakoi, H., and Goto, T. (1969). Cypridina bioluminescence. VIA new route for the synthesis of Cypridina luciferin and its analogs. Tetrahedron Lett., pp. 1609-1610. 

Kishi, Y., et al. (1966c). Cypridina Bioluminescence. III. Total synthesis of Cypridina luciferin. Tetrahedron Lett., pp. 3445-3450. 

Nakamura, H., et al. (2000). Convergent and short-step synthesis of dl-Cypridina luciferin and its analogues based on Pd-mediated cross coupling. Tetrahedron Lett. 41 2185-2188. 

Several papers were concerned with the synthesis of and mechanism of luminescence of Cypridina luciferin and its analogues <06T6272 06TL753 06TL6057>. 

Cypridina luciferin is an imidazopyrazinone involved in the bioluminescence of the crustacean Cypridina (Vargula) hilgendotfii. The first total synthesis of this natural product was achieved by Kishi in 1966, which was followed by that of White and Karpetsky in 1971. Most recently, Nakamura et al. developed a convenient, direct procedure for this synthesis, employing Suzuki coupling (Eq. (36)) [67]. 

The structure of Cypridina luciferin was established by analysis of spectroscopic data, chemical degradations, extensive MS analysis, and total synthesis [41—44]. Cypridina luciferin is biosynthesized from L-tryptophan, L-arginine, and L-isoleudne [45,46]. Distomadines A (24) and B (25) have been isolated from the asddian Pseudodistoma aureum and were not adive in antifungal, antiviral, anti-inflammatory, and anti-mycobacterial bioassays [47]. 

III. total synthesis of Cypridina luciferin. Tetrahedron Lett 1966 7 3445-50. 

EtMeCHCOCHO in aqueous acid gave the luciferin from Cypridina in 80% yield,which contrasts with the yield of <1% from the multistage synthesis. 

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