67 ^<13>C-NMRの配糖体の立体化学研究への応用
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概要
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In continuation of our studies of application of ^<13>C NMR to chemistry of glycosides, the structure of a glucoside(3) of Siegesbeckia pubescens (Compositae) including absolute configuration of its aglycone(2) was established mainly by means of ^<13>C NMR. Comparison of the spectrum of 3 with that of darutoside, the glucoside previously isolated from S. orientalis proved the identity of both compounds, leading to revise the location of the glucosyl-linkage of darutoside proposed by Diara et al. Significant influences of an adjacent OH function on the glycosylation shifts have been observed (see Chart 3). In order to find the generality of such an effect, stereo-selective synthesis of glucosides of cyclohexane-1, 2-diols (trans: 6R and 6S; cis: 7) by enzymic trans-glucosylation were studied. On glycosylation with α-amylase and maltose (donor), a racemic mixture of 6R and 6S yielded selectively mono-β-D-glucoside of 6R(8), and 7 gave exclusively 11 though the reaction of the later proceeded evidently more slowly than that of 6R. In contrast to this, glycosylation with β-glucosidase (emulsin) using amygdalin or salicin as the donors yielded less stereospecifically a mixture of glucosides, 9 and 10 from a mixture of trans diols(6R+6S), and 12 and 13 from cis diol(7) respectively. The configuration as well as the conformation of these glucosides were investigated and the glycosylation shifts were discussed in comparison with the former results.
- 天然有機化合物討論会の論文
- 1978-08-22
著者
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笠井 良次
広島大薬
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田中 治
広島大薬
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山崎 和男
Institute of Pharmaceutical Sciences, Hiroshima University School of Medicine
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山崎 和男
広島大薬
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山崎 和男
Institute Of Pharmaceutical Sciences Hiroshima University School Of Medicine
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木原 智加子
広島大薬
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板野 加代子
広島大薬
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金 済勲
ソウル大・生薬研
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