51(P05) 完全重水素化メバロン酸を用いた古細菌細胞膜脂質の生合成研究(ポスター発表の部)

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Archaea (archaebacteria) including methanogens, extreme halophiles, extreme thermophiles, and thermoacidophiles are distinct from prokaryotes and eukaryotes. The most characteristic feature of archaea is found in the chemical structure of its membrane core lipid, the biosynthesis of which has been studied with new approaches. A synthetic method of (RS)-mevalonolactone-d_9 was developed starting from deuterated dimethoxyphenylacetone and trimethyl phosphonoacetate. The 7-steps synthesis yielded mevalonolactone-d_9 in 43% overall yield. Worth to note is that the deuterium sources were easily available deuterium oxide and lithium aluminum deuteride. Synthesized mevalonolactone-d_9 was applied to the biosynthetic studies of the core membrane lipid, 2,3-di-O-phytanyl-sn-glycerol, of two halophilic archaea, Haloarcula japonica and Halobacterium halobium. Mevalonolactone-d_9 was highly incorporated into the phytanyl chains of the archaeal lipid, and the total enrichment was approximated to be as high as 70-90%. Mevalonate pathway appears to be clearly responsible for the biosynthesis of the phytanyl chains of the core lipid in the archaeal membrane. Further, since fully deuterated mevalonolactone was highly incorporated to the phytanyl group, we were able to trace the fate of incoming protium atoms during lipid biosynthesis by ^1H NMR spectroscopy. Saturation of the geranylgeranyl group to the phytanyl group was shown to take place through the addition of hydrogen in a syn-manner by analyzing the behavior of protium on the heavily deuterated archaeal lipid.
天然有機化合物討論会の論文
1998-08-31

51(P05) 完全重水素化メバロン酸を用いた古細菌細胞膜脂質の生合成研究(ポスター発表の部)

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