Non-Enzymic Coupling of Vindoline and Catharanthine to Synthesize 3', 4'-Anhydrovinblastine under Irradiation with Near-Ultraviolet Light

概要

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Non-enzymic coupling of vindoline and catharanthine to synthesize the dihydropyridinium intermediate(DHPI) of dimeric alkaloids was achieved under near-ultraviolet light irradiation with a peak at 370 nm in the presence of flavin mononucleotide (FMN). Circular dichroism analysis showed that 3', 4'-anhydrovinblastine(AVLB), a reduced product of DHPI, had an α-configuration at the C-18' chiral center, like natural dimeric alkaloids. The amount of AVLB was about 50% of the initial amount of vindoline under the conditions optimized in the study, namely irradiation with 20 W/m^2 near-ultraviolet llight in the presence of 50 μM FMNand 1 mM manganous ion at pH 7 and 25℃. These results suggest that this non-enzymic coupling system can supply naturla DHPI in sufficient amounts under biomimetic conditions and that it is suitable for investigating subsequent one-pot biosynthetic reactions; for example, to detect the enzyme mediating vinblastine synthesis from DHPI.
社団法人日本生物工学会の論文
1997-03-25