eugenyl 6-O-β-D-xylopyranosyl-β-D-glucopyranoside | 18604-54-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: eugenyl 6-O-β-D-xylopyranosyl-β-D-glucopyranoside
• 英文别名: eugenol 4-O-β-primeveroside；forsythenside L；sasanquin；eugenyl β-primeveroside；(2S,3R,4S,5S,6R)-2-(2-methoxy-4-prop-2-enylphenoxy)-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxane-3,4,5-triol
• CAS: 18604-54-1
• 化学式: C₂₁H₃₀O₁₁
• 分子量: 458.463
• InChiKey: FSCNUJMKSQHQSY-OSLYEKKFSA-N

物化性质

• 熔点：
  197-198 °C
• 沸点：
  692.3±55.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  168
• 氢给体数：
  6
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  eugenyl 6-O-β-D-xylopyranosyl-β-D-glucopyranoside 在 Penicillium multicolor IAM7153 β-diglycosidase 作用下， 以 acetate buffer 为溶剂， 生成 D-吡喃木糖 、 丁香酚 、 primeverose 、 丁香酚葡糖苷
  参考文献：
  名称：

  Isolation and Characterization of a β-Primeverosidase-Like Enzyme fromPenicillium multicolor

  摘要：

  从多彩青霉IAM7153的培养滤液中发现了对p-硝基苯基和丁香酚β-樱草糖苷（6-O-β-D-木糖吡喃糖基-β-D-葡萄吡喃糖苷）的水解活性，并分离出了该酶。该酶通过硫酸铵沉淀，然后依次通过苯基琼脂糖、Mono Q和β-半乳糖苷酰胺亲和柱层析纯化，类似于一种β-樱草糖苷酶。通过SDS-PAGE和凝胶过滤法估算其分子质量为50 kDa。纯化的酶对底物p-硝基苯基β-樱草糖苷具有高度特异性，以内切方式裂解为樱草糖和p-硝基苯酚，但对一系列作为香气前体的β-樱草糖苷底物的水解作用轻微。在其水解作用和动力学分析中，该酶对二糖苷的糖苷配基和糖基部分表现出较窄的底物特异性。我们得出结论，目前的酶是一种β-二糖苷酶，而不是β-樱草糖苷酶。

  DOI：

  10.1271/bbb.70.691
• 作为产物：
  描述：

  丁香酚 、 p-nitrophenyl 6-O-β-D-xylopyranosyl-β-D-glucopyranoside 在 sodium acetate buffer 、 Penicillium multicolor IAM7153 β-primeverosidase 作用下， 以 水 为溶剂， 反应 3.5h， 以12%的产率得到eugenyl 6-O-β-D-xylopyranosyl-β-D-glucopyranoside
  参考文献：
  名称：

  Efficient Synthesis of β‐Primeverosides as Aroma Precursors by Transglycosylation of β‐Diglycosidase from Penicillium multicolor

  摘要：

  The enzyme activity transferring a beta-primeverosyl unit was found from culture filtrates of Penicillium multicolor IAM7153 and was useful for synthesizing a series of beta-primeverosides via a beta-primeverosyl transfer reaction in an aqueous-organic biphasic system. With the acceptors benzyl alcohol, 2-phenylethanol, and ( Z )-3-hexenol, the enzyme induced the transfer products benzyl, 2-phenylethyl, and ( Z )-3-hexyl beta-primeverosides in high yields of 51% to 70% based on the donor added. When geraniol and eugenol were used as acceptors, the corresponding geranyl and eugenyl beta-primeverosides were obtained in lower yields of 8% to 12%. The enzyme was an excellent tool for producing naturally occurring beta-primeverosides on a mmol scale.

  DOI：

  10.1080/07328300500439413

文献信息

• Isolation and Characterization of a β-Primeverosidase-Like Enzyme from<i>Penicillium multicolor</i>
  作者：Kazutaka TSURUHAMI、Shigeharu MORI、Satoshi AMARUME、Shigetaka SARUWATARI、Takeomi MURATA、Jun HIRAKAKE、Kanzo SAKATA、Taichi USUI

  DOI：10.1271/bbb.70.691

  日期：2006.1

  p-Nitrophenyl and eugenyl β-primeveroside (6-O-β-D-xylopyranosyl-β-D-glucopyranoside) hydrolytic activity was found in culture filtrate from Penicillium multicolor IAM7153, and the enzyme was isolated. The enzyme was purified as a β-primeverosidase-like enzyme by precipitation with ammonium sulfate followed by successive chromatographies on Phenyl Sepharose, Mono Q, and β-galactosylamidine affinity columns. The molecular mass was estimated to be 50 kDa by SDS–PAGE and gel filtration. The purified enzyme was highly specific toward the substrate p-nitrophenyl β-primeveroside, which was cleaved in an endo-manner into primeverose and p-nitrophenol, but a series of β-primeveroside as aroma precursors were hydrolyzed only slightly as substrates for the enzyme. In analyses of its hydrolytic action and kinetics, the enzyme showed narrow substrate specificity with respect to the aglycon and glycon moieties of the diglycoside. We conclude that the present enzyme is a kind of β-diglycosidase rather than β-primeverosidase.

  从多彩青霉IAM7153的培养滤液中发现了对p-硝基苯基和丁香酚β-樱草糖苷（6-O-β-D-木糖吡喃糖基-β-D-葡萄吡喃糖苷）的水解活性，并分离出了该酶。该酶通过硫酸铵沉淀，然后依次通过苯基琼脂糖、Mono Q和β-半乳糖苷酰胺亲和柱层析纯化，类似于一种β-樱草糖苷酶。通过SDS-PAGE和凝胶过滤法估算其分子质量为50 kDa。纯化的酶对底物p-硝基苯基β-樱草糖苷具有高度特异性，以内切方式裂解为樱草糖和p-硝基苯酚，但对一系列作为香气前体的β-樱草糖苷底物的水解作用轻微。在其水解作用和动力学分析中，该酶对二糖苷的糖苷配基和糖基部分表现出较窄的底物特异性。我们得出结论，目前的酶是一种β-二糖苷酶，而不是β-樱草糖苷酶。
• Efficient Synthesis of β‐Primeverosides as Aroma Precursors by Transglycosylation of β‐Diglycosidase from <i>Penicillium multicolor</i>
  作者：Kazutaka Tsuruhami、Shigeharu Mori、Kanzo Sakata、Satoshi Amarume、Shigetaka Saruwatari、Takeomi Murata、Taichi Usui

  DOI：10.1080/07328300500439413

  日期：2005.11.1

  The enzyme activity transferring a beta-primeverosyl unit was found from culture filtrates of Penicillium multicolor IAM7153 and was useful for synthesizing a series of beta-primeverosides via a beta-primeverosyl transfer reaction in an aqueous-organic biphasic system. With the acceptors benzyl alcohol, 2-phenylethanol, and ( Z )-3-hexenol, the enzyme induced the transfer products benzyl, 2-phenylethyl, and ( Z )-3-hexyl beta-primeverosides in high yields of 51% to 70% based on the donor added. When geraniol and eugenol were used as acceptors, the corresponding geranyl and eugenyl beta-primeverosides were obtained in lower yields of 8% to 12%. The enzyme was an excellent tool for producing naturally occurring beta-primeverosides on a mmol scale.